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Intergenerational Friendship

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Marty and Doc, friends for all time.
Silvia Mora: The old men are sad characters.
Mabel Mora: I guess. Sort of. They're also the first friends I've had in a really long time.

Two people are good friends. Only, one of them is about twice, three times, — or even four or more times — the other person's age! Considering their differences in life experiences and worldviews, how do they relate? What could they possibly have in common? Assuming this is actually a platonic friendship and not something far more sinister, or for that matter an overtly stated mentoring situation, intergenerational friendships can be pretty weird. As the Real Life section indicates, while not everyone finds older or younger people completely unapproachable, there's still frequently a gap there.

This can take the form of a young adult from one generation befriending someone old enough to be their parent or even grandparent, such as in the comedy Finding Forrester. It can take the form of an adult befriending a misguided or vulnerable youth, as in the French film The Professional. Sometimes, the two happen to have more in common than they think, such as having surprisingly similar life experiences. Sometimes the younger generation is more mature, or the older generation is less mature; the latter especially helps writers to dodge away from worrying questions being asked about sexual attraction.

As for how they become friends, it could well be contrived circumstances that bring them together, or a shared life experience. Sometimes it's a teacher trying to help a troubled teen, leading to them becoming close friends. Either way, the situation that leads to their friendship would often be something out of the ordinary, since in real life, people of two widely different age groups generally do not reach out to each other.

Sadly, though, if it's an adult and a child who are friends, in modern stories, expect someone to misinterpret it as being sexual, and violence to possibly result. Sometimes the younger one will have an innocent Precocious Crush on the older one.

This trope does not generally apply if it's a parent-child relation between the two.

A subtrope of Odd Friendship.

Contrast Age-Gap Romance and May–December Romance, in which there is a generation gap between romantic partners, and Intergenerational Rivalry, in which there is a generation gap between rivals. Although neither trope is mutually exclusive and can sometimes overlap.

Sister Trope to Mayfly–December Friendship, which involves friendship between beings of vastly different lifespans.


Examples:

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    Anime & Manga 
  • .hack//SIGN: Bear (middle-aged writer) and Mimiru (high school student). Gamers from different generations playing a virtual reality MMORPG. "You know, when I was your age, we actually had to use graph paper to map out the mazes in games." "You are old."
  • After the Rain (2014): Kondo, a 45-year-old divorcee, insists that he sees his relationship with the much younger Akira (a 17-year-old highschool student) as a non-romantic friendship. She isn't thrilled about the "non-romantic" part.
  • Arabian Nights: Adventures of Sinbad: Sinbad and his two friends Ali Baba and Aladdin all greatly differ in age, with Sinbad being a child, Ali Baba being somewhere in his twenties, and Aladdin being an old man of undetermined age.
  • Black Butler:
    • Vincent Phantomhive (late 20´s?) with Undertaker (at least a century) and Baron Kelvin (in his 50´s).
    • Ciel (13) has a Villainous Friendship with Sebastian (a demon). Also he´s at least in good terms with the aforementioned Undertaker until the Campania Arc and Lau (early 30's).
    • Agni (an adult) with his master Soma (late teens) and tries to be a friend with Sebastian
  • Bleach:
    • Nel, who is a child, and Ichigo, a teenager. Then, we find out that Nel is in fact the former Tres Espada and much older than Ichigo.
    • Captain Hitsugaya is the Shinigami equivalent of a Teen Genius and looks like a 15-year-old. Captain Ukitake is at least a 30-something-year-old in looks. Ukitake wants to strike one of these with Hitsugaya. Hilarity Ensues.
  • BL Metamorphosis is about an unlikely friendship between 17-year-old Urara Sayama and 75-year-old widow Yuki Ichinoi; when Ichinoi picks up a volume of BL manga out of curiosity and finds she enjoys it, she goes back to the bookstore to get more, and forms a friendship with longtime Yaoi Fangirl Urara from there.
  • Captain Tsubasa:
    • Roberto (late 20's/early 30's) and Tsubasa (12 at the start of the series).
    • Also Hyuga (12-13 at the start) and Kouzou Kira (mid to late 30's).
  • Cardcaptor Sakura: Sakura (10) and Kaho Mizuki (20s). All of Eriol's friendships might count as well, taking Really 700 Years Old into account.
  • Case Closed:
    • The title character (a 16 year old in a 7 years old body) with a lot of characters: all the police officers, several FBI members (mostly Akai and Jodie), the detective children, Dr Agasa... In universe, several characters think he has this kind of relationship with Heiji Hattori (who is really of his same age).
    • The 16th film, Detective Conan Film 16: The Eleventh Striker has Kazumasa Nakaoka (24) and Tomofumi Motoura (about 10-11 years old), who was an aspiring soccer player. It doesn't end well.
    • In the anime, Heiji himself has one with the 30-something restaurant owner Heishirou Bizen. Sadly, Bizen is stabbed to death in the seventh Non-Serial Movie.
  • Claudine: The psychiatrist is at least middle-aged when he meets the ten-year-old Claude. Despite the large age gap, they both share a lasting friendship. The psychiatrist explicitly refers to Claude as a good friend in the ending narration.
  • Dr. STONE: Senku and Chrome (mid-teens) and Kaseki (60s), thanks to their mutual love of science and crafting. They get a rather sweet Friendship Moment in Chapter 57, where Kaseki laments that he never had friends growing up; Chrome says that they're his friends, and rejects the age difference by saying "What does that have to do with anything?", which brings Kaseki to tears.
  • Dragon Ball Z: Gohan and Krillin, particularly in the Namek saga, where they spend a lot of time working together trying to think their way around the much more powerful villains. The weird thing is that Krillin isn't much taller than the six-year-old Gohan.
  • Durarara!!: Shizuo Heiwajima (24) tends to develop friendships with people that are out of his age range, such as Simon (late 40s to mid 50s), Akane (10), the Orihara twins Mairu and Kururi (15), and Celty (200+).
  • Eyeshield 21: Sakuraba (a high school student) and Torakichi (a grade schooler) who is Sakuraba's biggest fan and one of Sakuraba's main motivators for improving himself.
  • Fruits Basket:
    • Hatori and Momiji. They seemed to bond after Momiji was forced to leave his parents as a child (when Hatori was 20), and they remain close at least until the beginning of the series. Hatori probably took it upon himself to be a Parental Substitute, but oddly enough, Momiji still sees him as a friend, not a father figure. They turn out to have quite a bit in common.
    • Also, Tohru (16) with Shigure, Ayame (same age as Hatori) and Ritsu (a college student).
    • Tohru's mother with Arisa Uotani, Tohru's friend.
  • Fullmetal Alchemist:
  • Full Metal Panic!: Sousuke (16) and Kalinin (40-50+ ?). Kalinin doesn't quite make it as Sousuke's father figure (Majid took that role), and is more of a intergenerational Heterosexual Life Partner (though this is most notably during their backstory where they spent more time together - Kalinin shows up a lot less in the present time of the series, though he technically is Sousuke's legal guardian).
  • Fushigi Yuugi: Byakko Ibun: the 20-something Nirusha and the 10-years-old Reipin, with the first helping out the latter to find her inner strength in exchange for her being kind to him when nobody else would.
  • Future GPX Cyber Formula: 14-year-old Hayato Kazami making friends with several of these; with Bleed Kaga (19), Naoki Shinjyo (17), Knight Shoemach (21), Jackie Gudelhian (20), Franz Heinel (21), Edelhi Bootsvorz (22) and on his team, with Tetsuichiro Kurumada (47) and Shinsuke Maki (19).
  • GaoGaiGar: Mamoru Amani (9) and Gai Shishioh (20).
  • In GATE Tarou Kanou was an up-and rising government bureaucrat in his mid-thirties, and Itami Youji was a troubled junior high kid. Both of them met on a street corner when Tarou saw that Itami was reading a Manga and got them into a discussion about their shared love for Manga. Now Itami is an illustrious and distinguished First Lieutenant in the JSDF, while Tarou Kanou is Japan's Defense Minister who is gunning for the Prime Minister seat, but twenty years since they first met; they are still fast friends.
  • Gintama:
    • The Yorozuya trio. There's Kagura (14) and Shinpachi (16) with their boss/comrade/friend/sorta-like-big brother Gintoki, who's somewhere in his 20s. Kagura even sleeps in Gintoki's closet.
    • Also Okita (18) and his beloved captain Kondo (30ish). Hijikata falls somewhere in-between.
  • Gugure! Kokkuri-san: Kokkuri is probably a lot older than the 25 years he'd like to claim. Kohina is an elementary student. Nevertheless, even though Kokkuri's acting as a parental substitute, they still consider each other friends.
  • Gundam
    • Mobile Suit Gundam SEED:
      • Mu La Flaga (late twenties/early thirties) and Kira Yamato (16). Later, we get Andrew Waldfeld (late thirties/early forties) and Kira.
      • Also Murrue Ramius (late twenties) and both Kira and his friends (15-16). By the end Natarle (same age bracket as Murrue and Mu) strikes one with Fllay (15) when she becomes her Bridge Bunny after her Character Development.
    • Mobile Suit Gundam Wing: Heero Yuy (14-15) and the little girl (no older than 8) and her dog. It doesn't end well. Holy crap, it doesn't.
  • Hetalia: Axis Powers:
    • Iceland (ageless nation with the looks of a 17-year-old) and Turkey (also ageless nation, looks like in his mid-to-late 30's). More exactly, the Hetalia Bloodbath 2010.
    • Also France (ageless nation who looks like in his late 20's) andf 19-year-old American tourist Lisa, the reincarnation of another 19-year-old girl he was friends with... Joan of Arc.
    • Rome (dead ageless nation with the looks of a man in his 40's) attempts to strike one with his grandson's best friend/boyfriend, Germany (another nation who looks like a 19-20 year old but may be "older" than that). Hilarity Ensues.
  • Hikaru no Go: Hikaru Shindou who is around 12 years old at the beginning of the story, and Fujiwara Sai, who is a couple hundreds years old ghost.
  • His and Her Circumstances: Maho Izawa (mid-teens) and Yuusuke Takeshi's (late 20's) relationship starts off as this when she was lecturing her friends, and he notices her leg was bleeding, and he claims he saw see a vision of a lovely schoolgirl holding flowers. This later becomes a May–December Romance when they started to fall in love and get married at the end of the manga.
  • Hunter × Hunter:
    • Isaac Netero, who is at least 110 years old or older, is shown to be friends with many people who are much younger than him. The Juuni-shin/Zodiacs, the Shingen-ryu Kenpo martial artists (including Wing and Biscuit), Morel, Knov, and many other Hunters are mostly adults of various ages. Even old characters like Linne and especially Zeno are not nearly as old as Netero (Netero was already an old man when Linne and Zzigg were young adults and Zeno is 67.)
    • The Phantom Brigade have a Villainous Friendship going on and the member vary in different ages. They even welcome Kalluto (10) and have accepted him as their friend...sort-of.
  • I Am a Hero: Hideo and Hiromi, at least initially, before it becomes something more sexual. This works primarily because they're forced together by circumstance, as they have very little in common.
  • Inside Mari: High schooler Yori and college student Isao befriend each other, when Isao ends up in the body of Yori's crush, Mari. Later subverted when it's revealed that Mari has a Split Personality rather than there being a body-swap.
  • Jewelpet (2009): Keigo Tatewaki (early 20's) with Rinko and her friends (14).
  • JoJo's Bizarre Adventure:
    • Joseph Joestar has been on both ends of that trope:
      • In Battle Tendency, he's a 18-year old delinquent who's close with the elderly Robert E. O. Speedwagon, his Honorary Uncle.
      • In Stardust Crusaders, he's the 68-year old leader of a team made up of teenagers (Joseph's grandson Jotaro Kujo, Noriaki Kakyoin), people in their 20s (Jean-Pierre Polnareff, Muhammad Avdol) and a dog (Iggy) and is very close friends with all of them.
      • In Diamond is Unbreakable, he's 78 years old. This doesn't prevents him from being one of the few people the 20-year old Rohan Kishibe openly likes, gets along with and respects.
    • In the tie-in game JoJo's Bizarre Adventure: Heritage for the Future, the middle-aged Hol Horse has a Villainous Friendship with the young boy Boingo. It later carries over to the series itself with JoJo's Bizarre Adventure: Crazy Diamond's Demonic Heartbreak, with Hol Horse striking up friendships with the teenaged Josuke Higashikata, as well as with Boingo's young adult brother, Oingo.
    • In Golden Wind, the 20-year old Bruno Bucciarati is friends with the Affably Evil Cool Old Guy Pericolo and is noticeably affected by the latter's suicide.
    • Stone Ocean's main cast has the 39-year old Weather Report and the 40-year old Jotaro Kujo being close with Jolyne Cujoh (Jotaro's estranged daughter), Ermes Costello, Emporio Alnino, F.F., and Narciso Anasui, all of whom are in their 20s at most (with the youngest, Emporio, being 11, aside from F.F. being a plankton colony possessing a young girl's corpse).
    • Lucy Steel has also been on both ends of the trope:
      • In Steel Ball Run, she's a 14-year old girl married with the 51-year old Stephen Steel, but their marriage is a sham to protect Lucy from The Mafia and the true nature of their relationship is actually this trope. While there's nothing romantic in their relationship, they're still much closer to each other than the average friendship. Part of Lucy's motives to help the heroes is to rescue her friend and husband.
      • In JoJolion, the now 65-year old Lucy befriends the 17-year old Joseph "Fumi" Joestar, and takes him under her wing when he is trapped in the US during WW 2. He becomes her assistant and looks after her in the three last years of her life.
  • Kaiju No. 8: 32-year-old Kafka Hibino's closest friends and Secret Keepers, Reno Ichikawa and Kikoru Shinomiya, are a good 10+ years younger than him. Even around the entire group of new recruits, he's still the oldest among them, yet he gets along well with all of them.
  • Kiki's Delivery Service: Kiki befriends three women, all of different ages. There was the pregnant baker lady, the teenaged artist and an elderly woman.
  • Kotaro Lives Alone: Kotaro, the 4-year-old protagonist, becomses good friends with his neighbor, a young adult named Shin Karino.
  • Kodomo no Jikan: Aoki-sensei (22) and the three girls (10 each) act like this from time to time. Kuro (10) and Shirai-sensei are an even better example.
  • In Kurage no Shokudo, Youtarou forms two with Arashi, the current owner of the Jellyfish Diner, and Natsuko, a close friend of Arashi's who delivers fresh produce to him.
  • Lyrical Nanoha:
    • Fate and Signum, who first became friends back when Fate was just 9 while Signum... looked and acted to be around 19 but is actually a few hundred years old.
    • Vita likes hanging out with senior citizens and looks like she's 6, but she's just as old as Signum.
  • Magi: Labyrinth of Magic: there's Aladdin (10) with his numerous friends and allies: Alibaba (17), Morgiana (14), Sinbad (29), Yamraiha (23), Ugo (originally 62 but became ageless), Sphintus (17), Kouha (18) and Yunan (unknown).
  • Miss Kobayashi's Dragon Maid:
    • Kobayashi (25) and Georgie (somewhere in her teens) instantly become "comrades" over their shared love of maids when they met.
    • Shouta (10) gets along really well with Takiya, considering him to be a cool adult.
    • Saikawa becomes friends with Ilulu in chapter 45, who (discounting lifespan differences) is about twice her age.
    • The sixth Mini Dragon short has Fafnir go to a guild meetup for an MMO he plays. Discounting Fafnir himself, the oldest person present is a middle aged man and the youngest is a woman in her late teens/early twenties.
  • Thirty-years-old Satoko Tawada befriends a 12-year-old Mashuu Hayami in My Boy.
  • In My Next Life as a Villainess: All Routes Lead to Doom!, a young gardener was hired by an equally young duke and they became fast friends. When the duke died the gardener was heartbroken and simply sat waiting to die so he could see his friend again. However, eight year old Katarina got him out of his funk by constantly hanging around him borrowing tools and making toys together until he eventually realized he was glad to be alive again. He still looks forward to seeing his old friend again, but now he wants to tell his friend all about his granddaughter.
  • Naruto:
    • Naruto and Killer Bee, with the former being a teenager and the latter in his mid-thirties.
    • There's also Itachi Uchiha and Kisame Hoshigaki. Itachi met Kisame while he was in his early teens and Kisame was in his mid twenties, and yet, they get along very well. Especially for Akatsuki partners, who kind of have a reputation for bickering. Even the guy whose partner is himself.
    • Most of the jounin sensei become this with their students, when said students rank up. For example, take Naruto and Kakashi (respectively 16 and 31) or Shikamaru and Asuma (16 and 31).
    • In Naruto Gaiden, Naruto, who is in his early 30's, strikes one with Sarada Uchiha and to a lesser degree Chōchō Akimichi, two girls who were both 11 years old at the time.
  • Negima! Magister Negi Magi:
    • Negi (10) and Takahata (mid 30's). Kind of makes sense as Takahata was a friend of Negi's father Nagi.
    • Within the Ala Rubra, Eishun is at least 10 years older than Nagi, and Albireo is implied to be even older than that. Jack Rakan is also probably at least a decade older than Nagi. And Takahata was about Negi's age back then. The only one within his same age range was Kurt Godel, who was no older than 14.
    • Chisame (14 as much) and Jack Rakan also seem to have a bit of an Odd Friendship going, as well, especially judging by her reaction to his death. Not to mention Chisame's seeming addiction to age-changing pills to make her a loli further emphasizes this.
  • Neon Genesis Evangelion: Misato Katsuragi (29) and Shinji Ikari (14). This is one of the show's many deconstructions, as while they get along pretty well, Misato bounces from Shinji's commanding officer at NERV to a Cool Big Sis at home on a near-daily basis, which keeps them from truly being able to relate to each other in a way that would be mutually beneficial. Things are clouded even further by the ambiguity of exactly what Misato feels for Shinji and both of them having massive emotional and psychological issues that prevent them from being able to meaningfully help each other with their respective problems.
  • One Piece
    • Several of Luffy's True Companions. Up until the Grand Line, all of the crew were in their late teens. Then came Chopper (15), Nico Robin (28), Franky (34), and Brook (88). Post-timeskip adds Jinbe, who's 46 by that point.
    • Also Luffy's friendship with Shanks.
    • Let's not forget Mr. 2, who is very keen on making speeches about his friendship with the Straw Hat Pirates and was eventually revealed in a 2019 databook release to be 30 when introduced.
  • Ouran High School Host Club: Eclaire Tonerre (16-17) and Tamaki's mother (most likely in her fourties).
  • Outlaw Star: Gene Starwind (aged about 20) and Jim Hawking (aged 11).
  • PandoraHearts: Any of Break's friendships count as this as although he doesn't look it he's nearly forty. His closest friends are Reim (26) and Sharon (23, although she looks 13) they've been friends since he was 24.
  • Pokémon: The Series: Professor Oak (about 50) and Ash (10 for the past 26 years or so) are fairly close even though the former taught Ash's mother in school. Possibly averted in that, at least on Oak's end, he first met Ash when he was the same age due to some accidental Time Travel.
  • Power Stone: Ayame Yumatara (14) becomes good friends with Apollus and Pride Falcon (both late middle-aged) over the course of their journey to find the Power Stones, to the point where she's willing to protect them by taking a powerful blast from a transformed Valgas.
  • Rakugo Tennyo Oyui: Suzu (12) and Akira (somewhere in her 20s). Suzu spends the great majority of the series hanging around high school students and old famous people from Japanese history. If it weren't for the tanuki, Ponta, she'd be the only person of her age around.
  • Rurouni Kenshin in general. Main protagonist Kenshin is, unusually for a shounen action series, all of 28 years old. He was fighting in the last war when most of the other characters were children.
    • Sagara Sanosuke is 19, yet they gamble, drink, and occasionally swap war stories (from the same war, no less).
    • Kenshin and 17-year-old Kaoru even more so. They eventually get married.
    • More vitriolic, but also quite loyal: Sanosuke and 10-year-old Yahiko.
  • Sailor Moon
    • The no-more-than-eight Chibi-Usa is good friends with Setsuna, who is at least in her late teens, but more likely early-to-mid twenties. Then throw in the fact that the Setsuna Chibi-Usa is friends with originally is the thousand-year-old (AND reincarnated) Sailor Pluto, and the gap is a bit bigger. In the manga, Chibi-Usa herself is over nine hundred but looks like a child, and even then Setsuna is significantly older than her.
    • Rei Hino (14) and Kaidou-san (early/mid 20's) in the manga. He actually was Rei's first love, but he married a girl his age and it didn't go beyond a kiss.
  • Persona 4: The Animation: Nanako Doujima (6) and all of her cousin Yuu's friends (around 15-16), but specially 15-year-old Naoto. We don't know how strictly old Teddie is, but his human form has the looks of a 15-year-old boy.
  • Saiyuki Ibun: Toudai (who will be known as the Goudai Sanzo) and the youkai Tenkai who would inherit the Maten Sutra before Koumyou Sanzo. Played with, as physically, Toudai appears much older than Tenkai who looks like a young child. But as a youkai, Tenkai could be easily be years older than Toudai while retaining his youthful appearance.
  • The Seven Deadly Sins: princess Elizabeth (16) is friends with the Seven Deadly Sins, all of which are older than her: Ban is around 40, Meliodas is at least 3000 and Diane and King are over 700. Actually any friendship the Sins have outside the group counts. And in the group itself, since there is a huge gap between them (Ban and Meliodas, King befriended Diane when she was a child and he was an adult and ruler...).
    • King Bartha too. Aside of Meliodas he befriended Threader and Arthur when they were children.
  • Simoun: The deep and mutual bond between sixteen-year-old Yun and Time Abyss Onashia, possibly the ultimate example in terms of actual age difference.
  • The Snow Queen (2005): Gerda (eleven) and Ragi (middle-aged) become friends. There are some shades of Parental Substitute.
  • Tsubasa -RESERVoir CHRoNiCLE-: Kurogane (mid-twenties), Syaoran, Sakura (teenagers), and Fai might count as this.
    • Fai would definitely qualify as this with just about everybody. Yuuko mentions in Acid Tokyo that he has already lived many times Kurogane's lifespan. In other words he is not exactly in his early twenties anymore, no matter how young he looks. In fact, he is most likely closer to Yuuko's age than most.
  • The Vision of Escaflowne: Selena Schezar/Dilandau Albatou (around 6 years old at first, later 15) and Jajuka (age unknown, but presumably in his twenties).
  • Wandering Son: Nitori and Takatsuki both make friends with two 20 to 30 something year olds named Yuki and Shiina when they were in elementary school. Takatsuki actually met Yuki when she was (non-seriously) flirting with him one day. It's implied Yuki recognized Takatsuki was also transgender and decided to toy with him. Despite Yuki being Mistaken for Pedophile once (by Shiina no less) she's otherwise presented as a Cool Big Sis.
  • Yuzuriha Nekoi (14) and Shiyuu Kusanagi (about 40) in X1999. The girl is in love with the man, but it's implied that he cannot be anything more than friends with her due to their age difference and squick factor. They get together in the anime, though.
    • An example from the same series is Subaru and Seishirou. It's not as obvious in X1999 where both are clearly adults, but in the semi-prequel Tokyo Babylon the age gap is much more visible, Seishirou being 25 while Subaru is only 16. Then Subaru falls in love with Seishirou.
    • Also, Kotori (high school student, around 16) and Kakyou (in his mid-to-late 20's). The second goes as far as possessing her body briefly when she dies to take her horrifying physical pain into himself, and then he says goodbye to her as she goes to Heaven, becoming the depositary of her last words.
    • For that matter, this is the bond that Karen (20-something Hooker with a Heart of Gold) and Seiichirou (30-something manga editor) strike with the younger Dragons of Heaven. (High school age, or in the aforementioned Yuzuriha's case, middle-school age.)
  • Xxx HO Li C: Watanuki (about 16) and Yuko (in her late 20's or so it seems), and Watanuki and Haruka.
  • Yugi and his friends in Yu-Gi-Oh! (all around 16) with Pharaoh Yami/Atem (over 3,000).
  • Yuri!!! on Ice:
    • Yuri Plisetsky (15) and Yuko Nishigori (25) strike up a friendship in Episode 3. Yuko helps Yurio train for the Hot Springs on Ice competition, and she even texts Yurio after he's gone back to Russia in Episode 4. In Episode 11, when Yurio thinks of all the people he's met who have influenced his feelings of agape, Yuko is one of them.
    • Mari Katsuki (30) and Minako Okukawa (somewhere in her fifties) are good friends even though Minako is stated by Word of God to be older than Mari's mother. They travel together to Barcelona to watch the Grand Prix Finals.

    Asian Animation 

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    Comic Books 
  • Asterix: Asterix's closest friend besides Obelix is the druid Getafix, who had his long white beard when all the rest of the cast (save Geriatrix) were children.
  • Batman:
    • The Caped Crusader has five Robins and three Batgirls, though four of the Robins and one of the Batgirls ended up his children, and the younger Batgirls report more to and are better friends with Barbara Gordon than Bruce.
    • Tim Drake was friends with the much older Harold Allnut, who is Batman's mute in house mechanic since they both like developing new gadgets. He bitterly brings up Harold's murder when Bruce sent him to ask another genius to help build a new Batmobile, angry that Harold is never mentioned following his death.
  • Johnny the Homicidal Maniac: The relationship between Johnny and Squee is something like this, with Johnny regarding Squee as a friend/little brother figure. It's entirely one-sided however, as Squee doesn't feel anything other than sheer terror towards him, and with VERY good reason.
  • Kings In Disguise: In the excellent but very grim Dark Horse Comics series involving hobos in the Great Depression, the main character is a young boy who ends up teaming up with a much older man while searching for his father. There's nothing sinister at all about their friendship, but many other hobos traveling with young boys are in exactly that sort of relationship, and they assume that these two are as well. That's not even mentioning the incredibly creepy old guy who tries to assault the protagonist at one point.
  • Lenore the Cute Little Dead Girl: Lenore and Ragamuffin is one of the most extreme cases. Biologically, Lenore is 10 years old and Ragamuffin is between 20 and 30 years old. The thing is that Lenore has been 10 for 100 years and Ragamuffin has been 20-30 for 400 years. So they are like 4 generations apart and Lenore is still the one who manipulates him like he is her toy... which he is, practically, since he is trapped in a small cotton doll. And even when he transforms into his old vampire self, he still follows her like a devoted servant... ahem... friend.
  • My Little Pony Micro Series: Their age difference is never specifically mentioned, but its clear that Twilight and Jade learn to appreciate each other across a generational gap. Jade and Princess Celestia are also old friends, and Celestia is at least a thousand years old.
  • Superman: Superman's relationship with Superboy (the Conner Kent/Kon-El version) and Supergirl is something like this. Although they're family -being his clone and his cousin-, Clark generally lets them have their own lives but remains close with them regardless.
  • Sweet Tooth: The main relationship is the friendship between Gus and Jeppard. Gus is 9, while Jeppard looks at least 40.
  • Tintin: Tintin and Captain Haddock. They fall in together during the derring do of The Crab With the Golden Claws and are constant companions from then on. It's difficult to determine when Tintin moves in with Haddock and Professor Calculus but it seems to be some time after the Moon adventure. The sheer oddness of their relationship has led to many snide remarks and speculation down the years, not least because neither are interested in women (the Captain's plain terrified), but theirs is a very sweet and lasting friendship where they continually lay down their lives for each other.
  • Werewolf by Night: In volume 1, 19-year-old Jack's best friend is Buck, a writer in his 40s. Jack occasionally wonders if Buck isn't a surrogate father to him, but then comes to the conclusion that, no, he simply is a very good friend. Later he grows to be best friends with Michael Morbius, who was already an M.D. with at least one PhD and a Nobel prize under his belt before Jack had even turned 18.
  • Wonder Woman:
    • Wonder Woman (1942): A couple of the Holliday Girls, who are a paramilitary group made up of young adults, are friends with a bunch of children who like to play on the streets of Washington D.C. which means that the kids will come tell them when there's suspicous activity or one of their friends has gone missing.
    • Wonder Woman (1987): The teenaged Wonder Girl (Cassie) becomes close friends the young adults Artemis and Donna Troy as well as the slightly older Diana.
    • Wonder Woman (Rebirth): The Kid Hero Peony McGill/Star Blossom jumps at the chance to befriend Wonder Woman.
  • X-Men:
    • Wolverine and every teenage girl to join the X-Men. In particular Jubilee in the 80s-90s, Kitty Pryde and Armor. In fact, he appears to get along with teenage girls better than any other type of person.
      • Lampshaded in an old Wolverine issue when he is asked, "do you wonder, why this need for adolescent girls?" - to which Jubilee replies "coz we don't screw his heart and backstab him after like you [adult] cows always do".
    • X-23 has one with Gambit in her series. It's not as pronounced as there's only a decade between them at most, but X-23's vulnerability is presented as a sharp counterpoint to Gambit's street smarts and maturity.
    • X-23's little sister Gabby has a surprisingly sweet friendship with fellow Cloud Cuckoolander Deadpool.
    • Cyclops is close to the other founding members of the Champions. His younger self was part of their team when he came to the present Marvel universe, and when he went back to his place in time the adult Scott gained all those memories.
    • Kieron Gillen's Uncanny X-Men run depicted Hope and Namor as this. Hope's a 16 year old Child Soldier and the messiah of the mutant race who grew up in a Bad Future, Namor is an Older Than He Looks Atlantian king who's been around and active since WW2; together they trade snark when paired up on a mission and connect as friends, something both of them rarely do with anyone else.
  • Yoko Tsuno: Yoko (early 20's) and Aoki (60/70's) in Daughter of the Winds. It ends in tears when Aoki, an ex-war veteran, pulls an Heroic Sacrifice for her sake.
  • Comic BookŻyjesz: In Polish graphic novel "Żyjesz?" ("Alive?") the nameless heroine of the book is in her 20’s, while the boy she befriends during her adventures is about six-seven years old. They get along pretty well, enjoy each other company and there isn't a single occasion where they aren't trying to save each other (the entire story line is more-or-less Survival Horror the comic book).

    Comic Strips 
  • The five-year-old titular protagonist of Dennis the Menace (US) tends to be on his elderly neighbor Mr. Wilson's good side whenever the latter is friendly.
  • The titular character of the British comic strip Rupert Bear and its Animated Adaptation Rupert is a young boy, but quite a few of his closest friends are adults, the most notable ones being the Professor, the Wise Old Goat, and Constable Growler.

    Eastern Animation 
  • All nine main cast members of KikoRiki are friends of different ages. It can be inferred from their manner of speech, interests and mannerisms that 2 are seniors (Carlin and Olga), 3 are middle-aged (Dokko, Pin and Barry) and 4 are youngsters (Krash and Chiko are kids, Rosa and Wally are teenagers).

    Fan Works 
  • In Everyday Craziness In Pontypandy, due to the lack of people her age around town, 18 year old Gabby's closest friends are 29 year old Elvis and 34 year old Bronwyn. She also has an Odd Friendship with 8 year old Norman.
  • In Gal Pals, Lincoln forms a friendship between the the titular Gal Pals, with half of them being teenagers (Carol, Becky, Whitney and Dana).
  • Getting Back on Your Hooves has Trixie form one with the Cutie Mark Crusaders after she saves them from a Ropen in the Everfree Forest (though Sweetie Belle already liked her before then).
  • In Ghoul Detective Series, Ken Kaneki befriended Kuroto Kai when he was a child and idolizes him. Sadly, Kai died two years later. Even their last conversation is a nod to Elena and Rei's last conversation.
  • Flippy and Flaky from the Happy Tree Friends in a lot of fancomics, fanart and stories, especially their anime versions. Bonus added with the Wife Husbandry that happens later.
  • Lots of The Lord of the Rings fanfiction portrays Legolas befriending Aragorn as a child, such as in Healing Hope.
  • In Hellsister Trilogy, twenty-nine-year-old Supergirl and her cousin's teen descendant Laurel Kent get along pretty well. Kara was particularly delighted to meet Laurel because her existence meant her cousin and Lois Lane would end up together.
  • The Parselmouth of Gryffindor has one develop between Ron and Peter Pettigrew.
  • In the Dark World timeline of the Pony POV Series, Twilight forms one with Pinkie's descendant Apple Pie. This is even more so than initially apparent, as one remembers that Twilight is over a thousand years old by this point.
  • In Scar The Unsung Hero, Scar (who must've been in his 60's in lion years at least considering it takes place after the movie) befriends a teenage boy. What's weird is that he ends up considering him not only an adopted brother but a "big brother".
  • The Second Try has one develop between 4 year old Aki and 14 year old Rei. This is especially interesting because Aki technically hasn't been born yet when the two meet. And because she is also the child of Asuka and Shinji, therefore she's Rei's niece. Sorta.
  • TD of The Non-Bronyverse gets along extremely well with children, but he's especially close friends with the CMC.
  • In the Gravity Falls fic Home Is Where the Haunt Is has one between Mabel and OC Mr. Mason. It doesn't end well.
  • In the Transformers fanfiction, Black Crayons, Annabelle Lennox is about five years old and considers Ironhide to be her best friend.
  • In the Fairly Oddparents fanfiction, Never Had a Friend Like Me, there is Norm, the 50,000 year old genie, and Amanda, the 8 year old human.
  • In Hope for the Heartless (a fanfic taking place after The Black Cauldron), the Horned King is an over one thousand years old lich, who's Resurrected For A Redemption Quest. He gains as his Morality Pet Avalina, a 14-year-old peasant girl (who turns 15 during the story), though he shows signs of becoming her deceased father's replacement.
  • In Kage, this seems to be forming between the 12-year-old Jade and the nearly 100 years old Raythor (who's middle-aged by his species' standards).
  • In The Ultimate Evil, Valerie Payne, who's 23 years old in the beginning of the fic, forms a sisterly bond with Jade Chan who's about ten years old.
  • The New Recruit: Matt is 17-18 when he joins the Avengers (all of whom are in or around their thirties). Despite this, they all seem to get along fairly well, with Bruce acting like a mentor figure for Matt.
  • In build your wings on the way down Edward becomes friends with Gabby and Aviv Seif, who are regular university students while he's 12. Lampshaded by Aviv, who also points out that Edward is part of the military.
    Aviv: When you were twelve, you would have been very happy to have seventeen year old friends.
  • Due to his abilities, Harry Potter in Barefoot doesn't see Dumbledore as his headmaster but as Albus and the two regularly chat in his office over various things. To a lesser extent, Harry and Tonks who's in her final year of Hogwarts while he's in his first.
  • In the One Piece/Steven Universe crossover A Gem in the Rough, Petrea and Damian (Miss Valentine and Mr. 5 respectively) do not mind that Steven Universe is far younger than they are and truly see him as a good friend. By the same token, Steven, Connie Maheswaran, and Genevieve (Miss Goldenweek) all get along with the older members of the crew quite well. On the other hand, this trope also unnerves Priyanka Maheswaran when she first meets the Straw Hats, but she warms up to them in time.
  • Black Sky has Theodore Nott - freshly out of Hogwarts so in his late teens or early twenties - going undercover in the Vongola Famiglia by becoming Daniela Vongola's personal attendant. He comes to see her as a surrogate grandmother while she fondly nicknames him "Accomplice" for his help in pranking the staff. Their bond was so deep they Harmonized with each other, something possible only when both parties have common ground.
  • Fate Ingens Cor: the fourteen-years-old Luna Lovegood and her Servant Caster - middle-aged - have a very friendly relationship, with the girl being genuinely curious about his original time period and the Servant happily telling her everything about nature magic and how lucky he was in his marriage.
  • In Eleutherophobia, Eva and Tom bond over being former involuntary hosts and run a support group together. She's old enough to be his mom.
  • The Bridge: several, often between the transferred kaiju and the younger Equestrians.
    • Between the earth pony filly Gentle Leaf and the 77,000 year old kaiju, Anguirus; started with them finding each other while lost and Gentle Leaf being endangered spurring Anguirus to launch himself into the fray against several dragons to protect her.
    • Destroyah and the Cutiemark Crusaders eventually work towards this, inspired by Destroyah accidentally saving them from a Timber Wolf pack and being knocked out before she could turn on them. She did go through multiple Defrosting the Ice Queen moments to mellow her out and after a Heel–Face Turn, allows them to ride on her back.
  • In Amazing Fantasy, the 14-year-old Izuku strikes up a friendship with the 47-year-old Peter Parker when they meet under surprising circumstances.
  • Held Together By Spiderwebs centers on teenage Peter Parker befriending late twenties Steve Rogers.
  • The Differentverse: Young Scootaloo becomes close enough to the other Bearers, all of whom are adults (and one of whom is her aunt), to have a bond of friendship that lets them activate the Elements of Harmony together.
  • The main team of the Alternate Tail Series mostly has young adults ranging from 17 to 19 with Gajeel, Levy, Lyon, and Mira. However, it also has from the much younger Kagura and Carla at 13 and 6 respectivly as well as the 198 years old Pantherlily, who is described as being around middle-age spiritually. The fact he is also Carla's father helps add to this trope.
  • The Last Son has many examples of this trope with the large amount of superheroes, but one of the most prominent examples is Superman with Captain America. The latter is a World War II veteran, while the former grew hearing the latter's stories and aspired to be like him when he decided to become a hero. When the two finally meet each other, they become fast friend over their shared ideals, and remain staunch allies throughout the story.
  • Son of the Sannin has Shizune and Itachi, who are about ten years apart in age and are shown to have become close friends by the time that the latter is a preteen. It's through this friendship that Shizune met Itachi's cousin Shisui, who she would marry and start a family with during the Time Skip.
  • The Phineas and Ferb fanfic A tale of two inventors: An unlikely friendship has a high-school age Phineas befriending his science teacher Dr. Heinz Doofenshmirtz.
  • Fate Revelation Online: Well, teenage version. To kids, the difference between an eighteen year-old and a twelve year-old is huge, so Asuna sees her friendship with Illya as something like this. Of course, the audience knows that Illya really is eighteen (though she enjoys playing up her appearance a bit), so she has more in common with her than Asuna realizes. On the other hand, everyone assumes that Illya and Silica are the same age so their friendship makes perfect sense, but in reality Illya is at least six years older.
  • In The Mouse in the Walls, due to Mirabel's Black Sheep status in the village and family and the fact that Ratón lives alone in the wall of a person's house in secret, they are pretty much the only friends they have despite one of them being in the mid-teens and Ratón pushing fifty.
  • In The Story of Apollo, Daphne and Luca: An Italian Tragedy, the teenaged Alberto immediately becomes good friends with the adult woman Caterina, Giulia's mother.
  • Later, Traitor: As Frazie (a teenage girl) begins to help the kids of Whispering Rock, she develops friendships with them. She's the closet with Lili, as the two become pals and work together to solve the mystery of the missing campers.
  • With Pearl and Ruby Glowing: The Palace support group has a mix of people of all ages, so friendships forming between the kids, teens, and adults are common, such as teenager Merida with adult Basil.
  • Oni Ga S Shiku Series: Izuku, at eight years old, is already good friends with Detective Tsukauchi, who is twenty nine at the time. At one point Tsukauchi asks Izuku to pretend to be his adopted kid for a bit so he can pretend he has some kind of social life in front of his mother, but both find it incredibly awkward and the mother tells Izuku she's glad her son has friends like him. It goes even further when Izuku at age ten goes to face the Yamikumo clan on his own, and instead of trying to stop Izuku Tsukauchi ignores all police proceedure to support him instead of telling him to stay back because he's a kid. This is in contrast to what the actual parental figures in Izuku's life do, who try to stop him from putting himself in danger.

    Films — Animation 
  • Wreck-It Ralph: Vanellope and Ralph. Somewhat murky since, as video game characters, they don't age normally, but Vanellope certainly looks and acts the part of a small child and Ralph is definitely an adult, and he looks like he'd be old enough to be her father. Also, Ralph's game is much older than Vanellope's, so it works on that level as well.
  • Hogarth (nine years old) and Dean (early to mid thirties at most) in The Iron Giant.
  • Carl (an elderly man, and the main protagonist) and Russell (a kid) in Up.
  • Jack and North in Rise of the Guardians. Jack is a little over three hundred years old but North, being Santa Claus, existed even longer. And that is not taking their physical appearances into consideration where Jack is a teenager and North is around his fifties or sixties.
  • In The Pirates Who Don't Do Anything: A VeggieTales Movie, the main protagonist George befriends a princess named Eloise. George is a rather old man and he has children back home who are around Eloise's age. Eloise is eight.
  • Alice and Tati from The Illusionist (2010). Alice is a teenager, and Tati is at least 60. Doubles as Odd Friendship because of their language barrier; Tati is French, and Alice can only speak English.
  • Toothless and Cloudjumper in How to Train Your Dragon 2. Toothless is stated to be Hiccup's age (about 20), while Cloudjumper was an adult when he accidentally left a scar on the newborn Hiccup's chin. The friendship mostly consists of Toothless behaving like a kitten/puppy trying to play with Cloudjumper, only for Cloudjumper to be mildly annoyed and grudgingly playing back. At the end, Cloudjumper bows down to Toothless, after Toothless has proven himself to be an Alpha.
  • Tintin and Haddock in The Adventures of Tintin (2011), a young adult and a man at least in his late thirties/forties.
  • Mary and Max, from the film of the same name, a lonely nine year old girl in Australia and a 44 year old man with Asperger's Syndrome in New York.
  • Aladdin and Genie. The former is in his late teens, and the latter is well over 10,000 years older (though you'd never know it, to look at him).
  • Moana is a 16-year-old girl, while Maui is a centuries-old demigod.
  • In The Little Prince (2015): The Girl, who's 9 years old, and the Aviator, an old man who tells her about his meeting with the Little Prince. This also applies to the Aviator and the Titular Little Prince, since it happened when the aviator was an adult, while the Little Prince was a child.
  • The Breadwinner: Eleven-year-old Parvana becomes friends with the middle-aged Razaq who fought in the war with her Baba. After Razaq asks her to read him a letter that informs him of his wife's death, he asks her to teach him to read and write and pays her more than she thinks is necessary. He even offers her some of his apple and gets her Baba out of prison, even with a bullet in his shoulder.
  • Tigger and Roo are often shown to be friends, but their friendship is especially prominent in The Tigger Movie. It's not clear how old Tigger is, or if stuffed animals even age, but he appears to be clearly older than Roo.
  • Bill Bluff and Guy Graham in Doug's First Movie are a villainous example.
  • Miguel and Héctor in Coco. Though Héctor died at an age where he is old enough to be Miguel's older brother, they grew up more than a hundred years apart from each other and they become fast friends within a few hours of knowing each other. It's revealed that Héctor is Miguel's true great-great grandfather.
  • The Prophet: The young Almitra and clearly older Mustafa form a quick friendship upon meeting each other.
  • Jesper and the eponymous Klaus.
  • A Bug's Life: Dot is just a child, but is Flik's only real friend initially.

    Films — Live-Action 
  • Our Miss Brooks: Miss Brooks is friends with sixteen-year-old Walter Denton, and, to a lesser extent, Harriet Conklin and Stretch Snodgrass. However, Miss Brooks, herself, would surely object to the label "Intergenerational Friendship"!
  • Good Will Hunting: Will, the isolated, delinquent, genius teenager from the slums of Boston, and Sean, the middle-aged, dissatisfied and lonely community college psychology professor form a relationship that makes up most of the plot.
  • Finding Forrester is about a high school student, Jamal, who meets reclusive author Forrester, and the two become friends. This leads to funny moments such as when Forrester tries to act "hip" by speaking slang, leading to the infamous "You're the man now, dog!" phrase.
  • Home Alone and its sequel involve friendships between the prepubescent Kevin McAllister and an older stranger who appears creepy at first, but turns out to be nice. Said older stranger also ends up saving Kevin from the Wet Bandits.
    • In the first film, it's Old Man Marley, who shovels salt onto the sidewalks. Kevin gets sucked into a rumor by his older brother Buzz that Old Man Marley killed his family, which turns out to be untrue. In fact, when Kevin talks to Marley in a church on Christmas Eve, Marley reveals that he's estranged from his son, and Kevin encourages him to give his son a call. In the movie's climax, when the Wet Bandits have Kevin cornered, Marley smacks both of them in the face with a snow shovel and rescues Kevin.
    • In the second film, the Pigeon Lady is a homeless woman who lives above the New York Philharmonic Orchestra's stage in the Lincoln Center. She's lonely because people seem to always forget about her, and Kevin vows to remember her. After making this connection, the Pigeon Lady saves Kevin after the Wet Bandits threaten him with a gun in Central Park. She douses the Wet Bandits in bird seed, causing them to be swarmed by a flock of pigeons, distracting them long enough for Kevin to slip away. The next morning, Kevin gives the Pigeon Lady a Christmas present, cementing the friendship.
  • Lawn Dogs is about two disaffected outsiders, a 10-year-old girl and a 21-year-old lower-class man, who become unlikely friends after a chance encounter.
  • Leon (aka The Professional) involves an assassin who befriends a 12-year-old girl.
  • Taxi Driver is about a man who befriends a 12-year-old girl as well.
  • The City of Lost Children has a 9-year-old girl who befriends an intellectually disabled man whose younger brother was kidnapped.
  • Beautiful Girls has a very young girl (played by Natalie Portman from The Professional) and an older man.
  • In the Back to the Future trilogy, high school senior Marty McFly is probably elderly scientist Dr. Emmett Brown's only friend in town. At least in the movies, how they met and became friends is not explained. That relationship simply exists before the first movie begins.
    • Word of God later explained that the friendship started when Marty was around 13-14 years old. After being told for years that Doc Brown was a dangerous, crackpot lunatic, he snuck into Doc's lab to see for himself and instead was fascinated by what he saw in there and thought Doc's inventions were cool. Doc found him and was happy Marty thought he was "cool and accepted him for what he was". Doc then gave Marty a part-time job helping out with experiments, helping in the lab, and feeding Einstein. Read for yourself here.
    • Later it was established that Doc actually sought Marty out when the timing was right due to his knowledge of their future friendship.
      • Doc Brown had the idea for the flux capacitor (the device that allows time travel) after hitting his head when he fell while hanging a wall clock. He may have fallen due to being distracted by Marty (having traveled from 1985 to 1955) calling him on the phone. Therefore, to preserve the timeline, Doc Brown must become friends with Marty, so Marty will film the testing of the time machine, go back to 1955, and enable the invention of the time machine. Ever wonder why a mad scientist obsessed with time travel and clocks converted one wall of his house into a huge guitar amp? Because he knew it would make Marty want to come over to his house repeatedly. And he had all of it planned out years before Marty was born, based on watching a video of himself describing inventing the time machine and a letter describing its first use, given to him by . . . Marty.
      • It should be noted that in real life Micheal J. Fox and Christopher Lloyd are only 23 years apart. Marty was supposed to be a teenager despite Fox being 24 at the time and Doc Brown was supposed to be in his sixties despite being 47 at the time. A notable gap, but hardly the 50+ years of their characters.
  • Middle-aged accountant Henry "Mutant" Weston and nine-year-old Eric from Mr. Magorium's Wonder Emporium. Plus, Mahony and Mr. Magorium himself. Sure, she might be about 20-30, but he claims to be 243 years old.
  • The Fall centers upon the relationship between Alexandria (5), a young immigrant with a broken arm, and her reluctant father-figure Roy Walker (unknown — based on the actor's age, mid-20s), a paralyzed stuntman. Surprisingly, no one ever suspects anything "funny" between them; the fact that he's a paraplegic may be a factor, but even after hospital officials find out that Roy conned Alexandria into stealing him morphine, he's still allowed to see her.
  • The film Scent of a Woman is about a poor prep school student slowly developing one of these with a blind, medically retired ex Lieutenant Colonel who has hired him as aide.
  • Lost in Translation is about Bill Murray's character and Scarlett Johannson's character striking up a friendship in Japan, in part because they are both in unsatisfying relationships with their spouses. The ending is ambiguous over whether it is a romantic relationship, but it does not have to be. It's an even bigger gap seeing Johansen was 17 when she was filming it though her character was somewhere in her 20s.
  • The Man Without a Face features a disfigured recluse (played by Mel Gibson) who agrees to tutor a troubled young boy over the summer. Their friendship sparks suspicion amongst the town residents. (Of course, in the book... )
  • About a Boy. Will Freeman, a 36-year-old bachelor, and Marcus, an eccentric, introverted, bullied 12-year-old with a suicidal mother end up close, and Marcus benefits and gradually becomes more confident and "normal" as a result of Will's guidance. In keeping with modern concern about such relationships, Marcus's mother initially thinks Will must be a paedophile and has a go at him in public.
  • The Ultimate Gift has the rich twenty-something guy befriend the Littlest Cancer Patient.
  • Rigoletto, a man who's at least in his forties and probably older, is reluctently befriended by a young girl to whom he ends up giving music lessons. The other kids from her town end up befriending him as well, with some pushing from the young girl. The adults are pretty wary, due in large part because the man is pretty badly disfigured. It all blows up when it appears that Rigoletto attacked a child. In reality, the child had fallen off a small dam into a river, and Rigoletto jumped in after and rescued it. When he carried the child into the town, all people saw was a monstrous man carying what looked like a dead child. It... Didn't end well.
  • The Karate Kid movies:
    • Daniel LaRusso and Mr. Nariyoshi Miyagi in the first three movies. Miyagi teaches Daniel self-defense, while Daniel helps Miyagi cope with his grief over losing his family and later, the death of his father.
    • Miyagi and Julie in The Next Karate Kid.
    • It continues in The Karate Kid (2010) remake, with Dre and Mr Han. Then Dre calls Mr Han his best friend.
  • Buster with Elwood and Mack (and later, Cab), in Blues Brothers 2000.
  • The beautiful film Yaaba is about two African children befriending a very old woman, an outcast who is accused of being a witch.
  • Teenage boy Max Fischer and middle-aged man Herman Blume in Rushmore.
  • In Finding Neverland, James Barrie strikes up a friendship with the Llewelyn-Davies boys despite being old enough to be their father. It helps that James is very much in touch with his inner child and that two of the boys (Peter and George) often act mature beyond their years. And since the movie is loosely based off of the real life friendship between James and the Llewelyn-Davies family, this would be Truth in Television.
  • Crouching Tiger, Hidden Dragon: Jen strikes up a sisterly friendship with Lady of War Shu Lien, who is at least twice her age.
  • Terminator:
  • In Push, the 13-year-old Cassie and Nick, who is in his mid-20s, are reluctant partners when they are chased by the Division and the Triads. By the end, though, they develop a friendship. Of course shippers see something more
  • The Lord of the Rings: The Fellowship, all with varying ages. Gandalf and Legolas were definitely the oldest of the group,note  with Pippin being the youngest and Aragorn's age is stated to be 87. In fact, this even occurs between the Hobbits themselves. Pippin is still in his "tweens", (the age between 20 and 33 when a Hobbit comes of age), when the Fellowship set out from Bag-End. In comparison, Frodo is 51. This continues in The Hobbit where Gandalf becomes friends with Bilbo (who was fifty-ish). Also, Bilbo with the dwarves, particularly Thorin and Balin, who are both nearing the two hundreds. Even the younger dwarves like Fíli and Kíli are above their seventies.
  • In Montreal Main, a photographer in his late 20s becomes best buds with a 12-year-old boy. Whether or not there's some attraction there is ambiguous; Word of God states that the man "doesn't know what he wants".
  • Allan Quatermain and Tom Sawyer develop one of these in the film version of The League of Extraordinary Gentlemen.
  • Henry Travers who plays the heroine's father in Shadow of a Doubt was about seventy at the time of filming. Hume Cronym, who played his best friend, Herbie, was about thirty. Originally Herbie was supposed to be played by a must older actor but they liked Cronym so much they they cast him. What results is a charming Intergenerational Friendship.
  • Twelve And Holding has Gus (unknown age, but probably in his late twenties or older) and Malee, who has a Precocious Crush on him. While it's entirely platonic on his side, she takes it a bit too far... eventually culminating in her setting up a romantic candlelight dinner, complete with a robe which she drops to reveal herself to him. Fortunately, Gus doesn't feel the same way, and promptly calls her mother to take her home.
  • The nature documentary Chimpanzee observes the developing bond between Oscar a three-month-old orphan and Freddie the troop leader (likely in his twenties or thirties.) This bond is especially noteworthy as while Chimpanzees are considered capable of adopting orphans this was the first time it was captured on film and even rarer seeing as it was an adult male and the alpha male no less.
  • Paper Moon has Moses Pray and the recently-orphaned Addie Loggins bonding in their various con games against suckers.
  • In Sling Blade a grown man and a young boy become close friends.
  • Eventually, the father-and-son relationship that existed between Obi-Wan Kenobi and Anakin Skywalker evolved into a very close friendship, despite the sixteen year age gap.
  • Other movies: On Borrowed Time, Just You and Me, Kid and Butterfly
  • From The Counterfeiters, Sally, who is in his forties, and Kolya, who is around 20.
  • Tiger Bay revolves around the friendship between a Sympathetic Murderer and the 11-year-old girl he kidnaps after she witnesses his crime. Eventually, Love Redeems and he lets her go.
  • In G.I. Joe: Retaliation General Joseph Colton develops one with Lady Jaye.
  • Star Trek (2009): Possibly, with Spock Prime and Jim Kirk, considering Spock Prime is about 155 and Jim is 25.
  • In Sophie Scholl: The Final Days, the 21-year-old title character strikes up a friendship with her cellmate Else Gebel, who is in her late thirties.
  • My First Mister: 17-year-old Jennifer becomes friends with 49-year-old Randal.
  • Everything Must Go: Nick Halsey befriends a neighborhood kid named Kenny who he teaches to play baseball and how to make sales.
  • Bad Words: 40-year-old Guy Trilby is befriended by 10-year-old Chaitanya Chopra.
  • Ray and Dave in Off the Black. Over forty years separate the two of them, but they bond over baseball and the fear of never accomplishing anything in life.
  • Harold and Maude. The titular characters - a teenaged boy and a 79 year old woman.
  • The Hunger Games: Katniss and Peeta with Haymitch.
  • Man on Fire: Creasy starts out as a suicidal alcoholic until he gradually warms up to Pita, the little girl he's been hired to bodyguard. He decides to help her prepare for a swimming competition and sort of becomes a surrogate father to Pita, driving him to go on a rage-driven revenge quest after she's kidnapped and apparently killed.
  • Kid Detective (2020): Abe (32) and Caroline (16-17) develop a friendly bond while working on a crime investigation together. This is probably helped by the fact that Abe still has the maturity of a teenager.
  • The film Laggies focuses on one of these between twenty-eight year old slacker Megan (Keira Knightley) and high school girl Annika (Chloë Grace Moretz).
  • In The Garbage Pail Kids Movie, 14-year-old Dodger is shown to be on very good terms with his adult boss Captain Manzini, who is definitely a lot nicer and more considerate to Dodger than the titular Garbage Pail Kids.
  • MrBeans Holiday: Bean causes Stepan, a russian boy to be separated from his father on the way to Cannes. Although (understandably) Stepan is angry with him at first, they quickly strike a friendship as Bean attempts to return Stepan to his father.
  • In The Night of the Grizzly, Gypsy Cole, who's about five or six years old, becomes close friends with forty-something store assistant Hank (Jack Elam).
  • In Jasminum Eugenia is stated to be five and Zdrówko is... hmm. Old (the actor was sixty five while filming).
  • In Along With The GodsThe Two Worlds The grim reaper, Haewonmak, is an adult male, and the assistant Guardian, Deok-choon is an 18 year old girl, though they are both a thousand years old.
  • Jumanji: As a boy in 1969, Alan is good friends with Carl, one of his father's employees. When they meet again 26 years later, Carl (who's now a cop) understandably doesn't recognize him, then freaks out when Alan tells him. Alan uses the opportunity to trick Carl into letting him escape.
  • Knives Out: The elderly Harlan was close friends with his personal nurse, the twentysomething Marta. So much so that he decided to cut his family out of his will and leave everything to Marta instead.
  • Captain Jack Sparrow and Will Turner in the Pirates of the Caribbean franchise. Jack is older than Will - Will's father served under Jack during his (first) run as captain of the Black Pearl - but even in the first film, their friendship is clear.
  • Many films starring the 1930's child star Jackie Cooper were about his friendship with an adult man. Some of these include; Young Donovans Kid, The Bowery, Lone Cowboy, Treasure Island (1934), and Tough Guy.
  • Mackintosh and T.J. has a middle-aged drifter befriending a fourteen-year-old runaway.
    • All Monsters Attack: lonely kid Ichiro, aged somewhere around 8-10, has a close friendship with his late middle-aged neighbour Shinpei, who often babysits for him.
  • The Holiday: While on vacation in L.A. the 30-something Iris befriends Arthur Abbott, a retired screenwriter from the Golden Age of Hollywood. Arthur provides Iris advice on how to get over her ex-boyfriend and rebuild her self esteem. In return, Iris helps Arthur with his physical therapy so he can attend a Screenwriters Guild event honoring his work.
  • In The King Falstaff appears to be at least two decades older than Hal; according to the script Hal is 25 and Falstaff is 45 at the beginning of the film, while in the film itself it's mentioned Falstaff fought during the reign of Richard II (who ruled from 1377 to 1399, while Hal was born in 1386 and would've been around 13 when Richard was deposed). The two are close friends, with the older Falstaff often offering advice to young Hal.
  • The Intern is about the close friendship that develops between the thirtysomething Jules, the CEO of a fashion company, and 60-year-old Ben, the titular intern. Both of them are lonely, Ben due to being a retired widow and Jules due to being extremely overworked, so they fill void in each other's lives.
  • A Quiet Place Part II has Regan, a girl in her early-to-mid teens, and Emmett, a man who looks to be in his forties, as a Badass and Child Duo who form a close bond during their travels to the island. Emmett, who lost his family and has become a hardbitten cynic ever since, regains his faith in humanity and a purpose due to his relationship with Regan.
  • More Than Ever: Thirtysomething Hélène platonically bonds with the elderly Bent over their shared experiences with disease.

    Literature 
  • Fire and Hemlock: The protagonist befriends a man who she initially thinks is much older than her, but he seems to have been in his twenties when they first met; she later realizes that he isn't that old, it's just that to a child, all adults seem ancient.
  • Dragon Bones has a really weird example with 19-year-old Ward befriending Oreg, a ghost-like being who is almost as old as castle Hurog, which means over a thousand years. There are some other instances where mortals befriend supernatural beings, where this trope applies, but the weird thing about Oreg is that he looks 17 or so - younger than Ward. He's also The Woobie and frequently seems that age, or younger, too, especially when he's frightened.
  • In The Bartimaeus Trilogy, Bartimaeus is a demon, thousands of years old and was pretty close friends with Ptolemy and, in the end, is pretty close friends with Kitty and especially Nathanael; all three of them are/were in their teens at that time.
  • Blanche of The Blue-Nosed Witch, the youngest witch in Scurry 13, is best friends with the much older Josephine.
  • In The True Confessions of Charlotte Doyle, Charlotte is 13, while Zachariah is in at least his 60s. It makes sense to Zachariah, though:
    "I can assure you," he said with a slight smile, "Zachariah can be a fine friend."
    "And I can assure you," I returned, "that the captain will have made arrangements for my social needs."
    "Ah, but you and I have so much in common."
    "I don't think so."
    "But we do! Miss Doyle is so young! I am so old! Surely there is something similar in that."
  • In My Sweet Orange Tree, Zeze is 5, while Portuga, the Cool Old Guy he befriends is in his mid-40. Not quite a friendship, but certainly a case of Parental Substitute.
  • Stephen King uses this one repeatedly:
    • Low Men in Yellow Coats, the first story in Hearts in Atlantis (later made into a Film of the Book) is about a young boy who develops a friendship with the much-older psychic Ted Brautigan. The boy's rather self-centered mother harbors strong suspicions about Brautigan's intentions for her son, which figures heavily into his eventual capture by the inhuman creatures hunting for him at the end of the story.
    • Jake and Roland in The Dark Tower series. Jake is not quite a teen when they first meet, and Roland is well over fifty.
    • Pet Sematary, with the Crandalls (both eighty-something) and the Creeds (in their 30s, with two young children who also bond with their elderly neighbors). When they first meet, the narration describes Louis Creed's relationship to Jud Crandall by saying "he called this man a friend, as a grown man must do when he finds the man who should have been his father relatively late in life".
    • Apt Pupil has a thoroughly twisted version with Todd Bowden and "Arthur Denker" (who is actually a former Nazi concentration camp commander named Kurt Dussander).
    • The Bill Hodges trilogy (Mr. Mercedes, Finders Keepers, End of Watch) has a three-sided example with Power Trio Bill Hodges (late 60s), Holly Gibney (mid-40s), and Jerome Robinson (goes from 17 to 21 during the trilogy).
  • Sandor Clegane and Sansa Stark in A Song of Ice and Fire. Not quite a friendship, but rather a case of Enemy Mine.
  • The Tales of Dunk and Egg features the friendship between a 19 year old tall Knight and a young boy named Egg, which isn't a great deal of a age gap, but for the fact that the Knight is a lowly reformed street urchin and the boy is a Prince of the Ruling Family of the Seven Kingdoms.
  • Many books by Russian author Vladislav Krapivin feature this trope, with friendships between a child and a young adult, or a young adult and an elderly character.
  • Land of Oz: Cap'n Bill and Trot. She's the daughter of his first mate from when he was a sailor, they now wander around Oz together.
  • Treasure Island: Long John Silver and Jim Hawkins, even more unusual when you consider that they spend at least half the book as antagonists. Silver is almost explicitly a replacement father figure. At least it explains why Jim, whose own father recently died, takes a liking to Silver despite having been warned about a one-legged pirate.
  • Bless Me, Ultima: The friendship between Antonio and Ultima (not only old enough to be his grandmother, but also helped his mother birth him) is one of the central points.
  • Harry Potter:
    • Harry, a school-age boy, quickly strikes up a lasting friendship with Hagrid, who's in his 60s and is Harry's introduction to Magical Society. He becomes a regular visitor to Hagrid's house for tea and conversation throughout the series.
    • Harry becomes friendly with the elderly Professors McGonagall and Dumbledore as he continues to get into heroics disproportionate to his age. They both think highly of him, though while McGonagall maintains their teacher-student relationship more firmly, Dumbledore more readily makes use of Harry in his schemes.
    • Harry becomes friends with his godfather Sirius Black after discovering their relationship at age 13. It's complicated by the fact that Harry is eager for a family connection and an adult confidant, while Sirius has a tendency to project his relationship with Harry's father onto Harry himself.
    • Dumbledore is in his 110s but maintains many friendships outside his age bracket, including the renowned 600-plus-year-old Nicolas Flamel and the 60-something Hagrid. Being a renowned archmage and a senior staffer at a Wizarding School allows one to become very well-connected.
  • Tolkien's Legendarium:
    • The Hobbit: 51 year old Bilbo befriends Gandalf, who is older than time itself.
    • The Lord of the Rings:
      • Bilbo is nearly 80 years older than Frodo, yet they have a very close relationship.
      • Other examples include the several hundred years old Legolas and the 140 year old Gimli, and the friendship bordering on father-son relationship between Merry and King Théoden. However, one of the most prominent examples is the bond that forms between Gandalf (the "grandfather" of the Fellowship) and Pippin (the "baby" of the Fellowship) when they ride off to Minas Tirith together.
      • Frodo is in his fifties whereas Merry and Pippin are still very young; Pippin is still in his Tweens (the age between 20 and 33 when a Hobbit comes of age). The Fellowship ages vary wildly, therefore they all sort of fit this trope.
    • In Beren and Lúthien, Human warrior Beren and Elven King Finrod have a very close friendship and would give their lives for each other (and Finrod actually did). Beren is 33 and Finrod is 2,291 years old, being older than Beren's race, the Sun and the Moon.
    • The Fall of Gondolin: Tuor and Voronwë (who is at least several centuries older), become close friends after meeting each other in Vinyamar, to the point Tuor trusts him to protect his wife Idril during the battle.
  • Quite unexpected bonds fitting this trope are found in Conn Iggulden's Emperor series between Caesar/Brutus and Renius, the elderly gladiator who trained them and tried to kill them in their early teens. The bond between Caesar and Renius is founded almost immediately after the older tried to kill the younger, and lasts to the point where Renius dies trying to protect Caesar during the Battle of Alesia. The bond between Brutus and Renius is somewhat shakier at first, with the former vowing to kill the latter for what he did to Caesar. Though after traveling with Renius to Greece, Brutus comes to view him as the father he never knew. It is however unclear if Renius ever really feels any stronger bonds towards Brutus.
    • Another such bond in the series is between Caesar and Octavius.
    • Julius' friendship with Cabera. Caesar was all of 14 when he first meet Cabera, who was pushing eighty at the time, but is still strong and spry. When Cabera dies in the third book, it is close to twenty years later, though he had spent most of the decade-long campaign in Gaul partially disabled from a stroke suffered after using his quasi-magical healing gift on one of Julius' lieutenants.
  • In The Frog King, the main character Harry has a friendship with a homeless girl called Birdie.
  • Nearly every kids' novel written by John Bellairs features a relationship like this. Usually it is between a smart preteen who doesn't fit in with his/her peers and an eccentric elderly person who treats the kid like an equal, and they face the supernatural menace of the week together. Later on in each series, the kid usually brings in one or two new friends his/her own age who also become fast friends with the old person. Lewis Barnavelt had his Uncle Jonathan and Mrs. Zimmermann, who he introduced to Rose Rita Pottinger. Johnny Dixon had Professor Roderick Childermass, who he introduced to Fergie. Anthony Monday became friends with the elderly Ms Eells and her brother Emerson.
  • In Dan Abnett's Gaunt's Ghosts novel Armor of Contempt, Dalin Criid and Merrt are stuck in a training/punishment brigade and forge a friendship despite Dalin's being a new recruit, just old enough to join, and Merrt's being a battle-hardened soldier from the founding of the regiment. It continues in Only In Death. In Blood Pact, Merrt comes along to give Dalin moral support when he tells Hark about the twin.
  • Canadian teen novel Jack's Knife has a 14-year-old boy who lives with his overprotective mother, and an elderly man who served as a police officer and is also very knowledgeable about survival skills, as friends. The mother doesn't want her son hanging around this Cool Old Guy, and is completely against the relationship, always suspecting the worst.
  • A feature in the Haruki Murakami books The Wind-Up Bird Chronicle and Dance Dance Dance, both which feature a thirty-something year old man befriending a young teenage girl.
  • In The Dresden Files:
    • Harry Dresden and the Archive develop one of these.
    • After Proven Guilty, Harry and Molly are also this trope note . They bond over their shared interest in magic and rebellious teenage years- much to the annoyance of Charity, who worries for her daughter.
  • In the Warrior Cats series apprentices almost always end up being good friends with their mentors. Fireheart also becomes good friends with Yellowfang, who is old enough to be his mother or grandmother; in return, Yellowfang considers Fireheart the son she wished Brokenstar was.
  • The effects of prolong in Honorverse pretty much ensure that the age gaps in any relationship would be quite wider than we are used to.
    • Take Horace Harkness and Scotty Tremaine. The former is a grizzled veteran, brawler and smuggler of a noncom, and the latter a 20-year-old Ensign Newbie fresh out of Saganami Island in the first book. Twenty years and innumerable adventures later Master Chief Warrant Officer Sir Horace Harkness and Captain Prescott Tremaine are still together, with Sir Horace Harkness even hacking the Navy personnel files just to be with his younger friend.
    • Manticoran Admiral Lady Sonja Hemphill belongs to the generation of the title character's parents (she's the classmate of Honor's husband Hamish Alexander, who is forty years older than her), while her Havenite counterpart Admiral Shannon Foraker is at least fifteen years youger than Honor, but the ladies nevertheless become BFFs as soon as they meet, on the grounds of both being such huge Wrench Wenches.
  • The un-named 20-something protagonist of Kokoro befriends a much, much older man whom he calls Sensei, as well as Sensei's wife.
  • Ted and Colin from Two Weeks with the Queen, who strike up a friendship over both having to deal with loved ones being seriously ill.
  • 14-year-old Blacky is friends with his elderly next-door neighbour Darcy in the books Deadly Unna? and Nukkin Ya.
  • In Great Expectations, Pip and Joe, his sister's husband.
  • From Where The Heart Is, Novalee, a teenaged girl, meets Sister Husband, a woman at least in her late thirties/forties. We also have Novalee and Lexie, the nurse who took care of Novalee after giving birth to Americus.
  • In The Book Thief, the girl Liesel (ranging from age 12 to 14) becomes friends with a Jewish man Max, who is twice her age.
  • Beyond the Western Sea has Nathaniel (17) and Mr. O'Connell (50), also Maura O'Connell (15) and Mr. Drabble (30).
  • Sayuri and Mameha in Memoirs of a Geisha, who have a sisterly/mentor-like friendship between them.
  • In the Tiffany Aching sub-series of Discworld, Tiffany and Granny Weatherwax develop something along these lines, though Granny would probably be hard-pressed to admit it.
  • While most of the inhabitants of the magical worlds from Alice in Wonderland and Through the Looking Glass and What Alice Found There were pretty rude and dismissive of her, the White Knight temporarily befriended Alice, rescuing her from the Black Knight and escorting her to the end of the chess board. Some believe that the White Knight was Lewis Carroll's Author Avatar, given his own friendship with Alice Liddell.
  • Lawrence Block's detective character Matthew Scudder has a scrappy urban (read: black) 16-20-something kid following him around, and eventually helping him do things that a 60 something white guy can't get done. Matt even gives TJ his rent controlled apartment, in New York!
  • In Anne of Green Gables, Anne becomes friends with her best friend Diana's Great-Aunt Josephine, Mrs. Allan (the minister's wife), and her teacher Miss Stacy. In the sequel Anne of Avonlea, as a teacher she befriends her pupil Paul Irving, and Miss Lavender, who becomes Paul's stepmother. In Anne of Windy Poplars, she becomes friends with a young girl named Elizabeth, and in Anne's House of Dreams, she becomes friends with Captain Jim (who is in his seventies) and Miss Cornelia, who is fifty.
  • In Moses, Man of the Mountain, Moses's two closest friends are his father-in-law Jethro, who is at least twenty years older than him, and his second-in-command and eventual successor Joshua, who is some forty years younger than him.
  • after the quake. Landscape with flatiron. Junko, a girl past highschool-age and Miyake, a man in his mid-forties.
  • In Susan Cooper's King Of Shadows, 11-year-old actor Nat is transported back in time to 1599, where he forms a loving friendship with 33-year-old William Shakespeare. Nat's father killed himself and Shakespeare's son died at Nat's age, which is why they are drawn to one another.
  • In There Is A Happy Land by Keith Waterhouse, the 10-year-old Nameless Narrator becomes friendly with "Uncle Mad", a homeless, mentally simple adult man (implied to be at least in his thirties or forties.) Becomes crucial to the plot when Uncle Mad is accused of the murder and (suggested) rape of a local girl, and the narrator helps him escape.
  • The Belgariad, by David Eddings:
    • Most of Garion's friendships in the series are this, due to the fact that he is a teenager on a quest with a group of people who are all experienced warriors. Special mention should go to his friendship with Durnik (which formed before setting out on the quest, when Garion did have children his own age to play with) and with Silk (which was noted as being an especially close friendship compared to Garion's other relations).
    • Also, in The Elenium, there is Intergenerational Marriage between Sparhawk (the middle-aged Pandion knight, and the protagonist) and young queen Ehlana (on eighteen years old).
  • Diario de un Zombi has Erico (23) and Paula (8).
  • Mistborn: After joining Kelsier's oddball team of older men (most of them in their 30s at least), Vin (who is only 16) forms friendships with most, if not all of them.
  • Also from Brandon Sanderson, in The Stormlight Archive Kaladin is about 20, while his second-in-command and friend from Bridge Four, Teft, seems to be at least 40 or even more, with graying hair and beard.
  • Valkyrie and almost everyone else in Skulduggery Pleasant. With the exception of Fletcher, all her friends are 60-400 years older than she is.
  • In the Star Trek novel Paths of Disharmony, Eklanir th'Gahryn reflects on the value of these. In particular, his friendship with his much younger aide ch'Drena is highly important to him.
  • The relationship between the captured Russian officer Ivan Zhilin and his master's daughter Dina in Leo Tolstoy's short story A Prisoner of the Caucasus. Though the age difference was never specified, Zhilin was old enough to be married and Dina was stated to be about 13, this impliying a significant one.
  • Eva Luna:
    • Melecio (mid 20's) is in two of these: one with a much older woman nicknamed La Señora, the other with a 13-year-old Eva. When Melecio fully transitions and reinvents herself as Mimi, both friendships stay, and in Eva's case it's even stronger as they live together.
    • Eva and Elvira, the cook of the first house she worked in, who becomes her unofficial grandmother.
  • The Hunger Games: Haymitch develops this with both Peeta and Katniss.
  • Momo: Momo is a little kid. Her two best and greatest friends are Beppo, an old and reserved streetsweeper, and Gigi, a lighthearted young man who loves to tell tales.
  • Papelucho:
    • The 8-year-old protagonist strikes one with an old man at least in his 70's, when they're both hospitalised. Papelucho is there after the birth of his little sister Jimena and being operated on by mistake, the old man pretty much lives in the hospital since he has no living family. It turns out the geezer was actually loaded in cash, and leaves his riches to Papelucho and his family when he dies. To a smaller degree, Papelucho also befriends Berenice, the Hospital Hottie in her mid 20's who works as the specific caretaker of the old man.
    • Papelucho's old friend once had a much older friend, a rough Big Brother Mentor whom he worked with when he was around Papelucho's age. The older man disappeared all of a sudden, leaving behind a letter in which he promised to return some day and introduce him to his future family, but he never came back. One of the reasons why the older man cares for Papelucho so much is that he believes the kid to be the grandson of his long-lost friend.
  • In Little Lord Fauntleroy an old man gets to bond with his estranged grandson.
  • Bodger with both Luath and Tao in The Incredible Journey, though he's closer to the cat.
  • During Dan Abnett's Eisenhorn trilogy, Eisenhorn develops the sentiment that, had he and Pontius been born at around the same time, and had Pontius not been evil, they would probably have become incredibly good friends.
  • Eragon and any of his elf friends. In particular, Arya, who's about 80 years older than him.
  • The Malazan Book of the Fallen can take this to extremes, such as the middleaged/old human Whiskeyjack, who's about 50, striking up a friendships with Anomander Rake, who's a few hundered thousand years old.
  • Young Dr Aziz and Adela's friendships with both the elderly Mrs Moore and 45-year-old Cyril Fielding in A Passage to India.
  • The Power of Five: Matt and Richard's friendship could be viewed this way. It doesn't end well.
  • The titular, middle-aged Tom of Uncle Tom's Cabin and six-year-old Eva.
  • The Three Musketeers: At the beginning of the story, D'Artagnan is 19 and Athos is said to be twice his age. The age gap is explicitly noted in-universe, as well as the father/mentor role played by Athos. Throughout the story arc they become Fire-Forged Friends and part of a Band of Brothers.
  • The Railway Series has Duke in an intergeneration friendship with both Falcon/Sir Handel and Stuart/Peter Sam, the 2 younger engines even dearly nicknaming him "Granpuff" as a result. Seems to imply a grandfather/grandson relationship going on there. Aww.
  • Shadow Song revolves around the friendship of Avrum Feldman and Bobo Murphy, who met when they were 68 and 17 respectively. Avrum shares a similar friendship with Bobo's love interest, who was also 17 when she met him.
  • Welcome to Night Vale, the two main characters Diane Crayton and Jackie Fiero develop a friendship. Diane is old enough to lead the Parent Teacher Association, and Jackie Fiero is nineteen years old.
  • The Maze Runner:
    • Jorge gets along well with many people much younger than him in age, including Brenda and Thomas. In the case of Brenda, he might as well be a father figure, as she already lost hers in a horrific manner.
    • In The Kill Order, Mark and Trina with Alec and Lana turn into a makeshift family after the Flare took away their family.
  • Hercule Poirot is much older than his best friend/sidekick Hastings. Their age gap is not specified, but Poirot was already at a retirement age in The Mysterious Affair at Styles while Hastings himself was only 30 then. In the final episode of the TV adaptation, Hastings tells his daughter that Poirot was something like a father to him.
  • In Redwall, Methuselah, an elderly mouse, is one of the closest friends of the young hero, Matthias. The former assists the latter in his quest to find the sword of Martin the Warrior.
  • In the Deptford Mice trilogy, Audrey gradually develops a bond with the ancient Starwife, though at first she could not stand her, thinking her to be a mean old hag. There is a significance to this bond because Audrey becomes the Starwife's successor after her death.
  • In Before Night Falls, Reinaldo and Virgilio begin their lifelong friendship aged 23 and 54, respectively.
  • The Fourteenth Goldfish: Ellie becomes closer to her grandfather after he starts living with her and her mother, and starts going to school with Ellie.
  • The Last Dogs: Max, a younger yellow Labrador retriever, is friends with an older black Labrador retriever named Madame Curie. Her urging Max to discover the meaning of the symbol on her collar is what sets Max off on his journey: to find her and help her find the humans.
  • Power: Teenage Omishto is close friends with her elderly "aunt" Ama, despite the generational gap. This friendship is later brought into question at Ama's trial, when the judge implies that Ama may have been influencing her due to their age differences.
  • In Flavia de Luce, the eleven-year-old Flavia has a peculiar, intense, and devoted friendship with Dogger, who has been at war with her father and was then kept around as her father's handyman, chauffeur, gardener, or secretary, whatever his frail mental state allows him to work. Flavia has learned to handle his bouts of PTSD, and she has an enormous respect for Dogger who gives her whatever counsel she needs, watches over her, and offers her understanding when no one of her family does.
  • Dr. Erland with Cinder and the Rampion crew in The Lunar Chronicles. Erland is old enough to be the grandfather of most of them ( or father, in one case), and yet becomes a trusted member of the team.
    • Prince Kai and his father's advisor, Konn Torrin, also clearly have a strong bond, and Kai trusts him more than anyone.
  • Father Brown and Flambeau in Father Brown. Although no specific ages are given, there is a general impression that Flambeau is younger than the little priest.
  • Asperger Adventures: In Lisa and the Lacemaker, Lisa, who seems to be about twelve, befriends Granny May's sister Hannah, who is somewhere in her eighties. It's implied that Hannah has Asperger syndrome as well as Lisa, so they get along well.
  • Chocoholic Mysteries: In "Kidnapping Clue", Lee (then a teenager) meets and, after some initial nervousness, becomes friends with Inez Deacon, a retired schoolteacher.
  • The Little Prince: The narrator, an adult pilot, forms a deep friendship with the titular Little Prince, who is a little boy.
  • Beautiful Music for Ugly Children: Eighteen-year-old Gabe's only real friend besides Paige is his next door neighbor John Burrows, an elderly DJ who was the first person in the United States to play Elvis Presley on the radio. John is the only person Gabe knows who's as obsessed with music as he is. He even got Gabe his job as a DJ at KZUK.

    Live-Action TV 
  • Game of Thrones: Between Princess Shireen Baratheon who is 13-15 throughout the series and Ser Davos Seaworth, a grown man. He gives her a toy ship and talks with her, she offers to help him read and visits him when he is imprisoned.
  • Our Miss Brooks:
    • Miss Brooks' best friend and confidante is her landlady Mrs. Margaret Davis. Mrs. Davis states a few times that she is "sweet sixty" (i.e "The Big Game"). Miss Brooks is hinted to be in her late twenties in several episodes of the program.
    • Miss Brooks is friends with sixteen-year-old Walter Denton, and, to a lesser extent, Harriet Conklin and Stretch Snodgrass. However, Miss Brooks herself would surely object to the label!Miss Brooks is friends with sixteen-year-old Walter Denton, and, to a lesser extent, Harriet Conklin and Stretch Snodgrass. However, Miss Brooks, herself, would surely object to the label "Intergenerational Friendship"!
  • In Selfie, main characters Eliza and Henry are separated by a generation-their official ages are unspoken (the actors are some 16 years apart), but Eliza is most likely in her mid to late twenties, with Henry being at least ten years older than that. In one episode, she calls him a Baby Boomer, and he points out that he falls squarely within the parameters of Generation X, while Eliza is a Millenial. He expresses distaste with a lot of her generation's traits, and she points out their differing views on sex (which he refers to as "being intimate", she laughs at him for this).
  • Community: The study group consists of three Millennials (Annie, Troy and Abed), three Gen-Xers (Jeff, Britta and Shirley) and one Boomer (Pierce).
  • Boy Meets World has Mr. Feeny who considered the main characters his students his friends. This wasn't as present in the early seasons as Feeny was more of a stern but Reasonable Authority Figure, but by the end of the series run the line between teacher and student had blurred considerably. A season 6 episode has Cory and Shawn exploit this using their friendship with Feeny to get him to be lenient with them on a paper they hadn't turned in.
    • This is played completely straight with Mr. Turner and Shawn where Turner takes Shawn in after his dad takes off to go after his mom. and the two become friends. Turner himself from the start is portrayed as the cool teacher that tries to relate to his students assigning the students an X-men comic to use as a comparison to the Odyssey.
  • The Doctor in Doctor Who is several centuries older than the majority of his companions. Even Romana, a Time Lady and his equal, was younger by about six hundred years. The friendships (and occasional romances) that he strikes up with his companions form a core element of the series. Initially the age difference between the Doctor and most of his friends was measured in centuries; this later extended to millennia and, as of the end of Series 9, the gap is now measured in aeons.
  • Captain Jack Harkness in Torchwood is over a century older than the rest of the team at least at the outset. Three series later, the gap's increased to several millennia.
  • Sarah Jane Smith in The Sarah Jane Adventures is well into the Cool Old Lady age range. Her closest friends are all teenagers, other than the Doctor, of course, who out-ages her by centuries.
  • The study group members on Community run the gamut from late teens (Annie, Troy) to mid-thirties (Jeff, Shirley) to late sixties (Pierce).
  • Firefly has Badass Preacher Shepherd Book becoming unexpectedly good friends with Boisterous Bruiser Jayne.
    • By the end of Serenity, Mal and River.
  • Gabrielle starts one in Desperate Housewives when she befriends a lonely neighborhood boy, Eddie, who later turns out to be a serial murderer. The friendship only lasts for one episode, though.
    • Also, the housewives and Mrs. McLusky, who is older than them. On the show, friendships between people of different ages are not considered anything special and it is basically taken for granted that that once grown, children become friends with their parents' friends.
  • Lex Luthor on Smallville started off friends with Clark, supposedly because Clark saved his life. He was around 9 when Clark landed in Smallville, which when Clark was a high school freshman would make him a 21 year old who's best friends with a 14 year old. The Dawson Casting keeps this fairly unnoticeable, as both actors are really in their 30s.
    • He started out as the Big Bad, but following his own Heel–Face Turn and Lex's Face–Heel Turn, Lionel Luthor did his best to become friends with Smallville's main cast, despite being somewhere in his fifties, while they were all in their teens. He manages to pull it off pretty well with regards to Clark and Chloe. Hawkman has this with Stargirl, Clark, and Oliver; Perry White has it with Lois.
  • Lost has Locke form a friendship with 10-year-old Walt that Michael did not like at all. Heck, if you want to get technical, seeing as Locke is the only Flight 815 passenger who is middle-aged (not counting side characters like Rose and Bernard), any friendship with him and another Lostie is an Intergenerational Friendship.
  • Station Eleven: Arthur Leander had a genuine bond with Kirsten, one of the child actresses playing his onstage daughter.
  • Star Trek: Deep Space Nine
    • The show has a variation on this with the Dax symbiont being old friends with Benjamin Sisko, despite the symbiont being several times his age. It started with this trope applying twice with both the Dax symbiont and the Curzon host being significantly older than Ben, which is why Sisko calls Dax "old man" even when it's in the body of a young woman. This trope applies both ways simultaneously with Jadzia and Ezri as the hosts are much younger than Benjamin, while the symbiont is much older.
    • Another intergenerational friendship existed between O'Brien and Bashir, who were in their forties and twenties respectively when the show started. Bashir's naivete and O'Brien's occasional world-weariness meant that the age gap sometimes seemed a lot more.
  • Star Trek: The Next Generation
    • "Hero Worship" involves Data's relationship with a boy of about 10 or 11, who idolizes him for saving his life.
    • In "Pen Pals", Data becomes "pen pals" with a young alien girl, whose memories they have to erase because of the Prime Directive. Then later Data becomes friends with another young alien girl, which ends with his memories being erased.
    • Wesley Crusher and the rest of the crew. At first, he's around 16, and many of the crew are twice as old as he is, sometimes older.
    • Technically, this trope applies to Data's friendships with the crew since chronologically he's not much older than Wesley.
  • Star Trek: Voyager has Naomi Wildman, who was born on the ship, and former Borg drone Seven of Nine, who is closer in age to Naomi's mother, forming a strong bond.
  • The friendship between Octavius and Vorenus + Pullo in Rome.
  • In Buffy the Vampire Slayer, Giles begins as Buffy's Watcher but a deep friendship develops despite their many differences. This caused him to be sacked for having 'a father's love' for her. It also led evil werewolf catcher Cain to assume they were having a fling and make salacious remarks. They get rather angry at the insinuation.
    Willow: This is Giles. He's our grown-up friend. Oh! Not like that.
  • And of course, used again in Angel. As a vampire, Angel is several hundred years older than those closest to him. Despite that, he ends up becoming best friends with Cordelia.
  • Forever Knight is very similar to that with Nick (800yrs old) and Natalie (just over 30)
  • True Blood, too. Godric (2,000 years old) and Erik (1,000), Erik and Bill (roughly 150) among others.
  • Mick and Beth in Moonlight.
  • Duncan and Richie in Highlander: The Series and probably Duncan and Methos to a lesser extent.
  • The Twilight Zone (1959): Ben (well over 1000 years old, appears to be about seventy) and Jenny (probably about nine-ish) in the episode "The Fugitive".
  • Madison and JD on Harper's Island. Even though it mostly consisted of "hey watch me do bad stuff in front of you."
  • Omar and Butchie from The Wire: originally it looks like just a professional relationship, with the semi-retired Butchie as Omar's bank and the go-to man for third parties that want to contact him, but it becomes apparent that they have probably the closest relationship Omar has with anyone except possibly his grandmother. Butchie's torture and murder is what brings him out of retirement.
  • In ER, Sam's son Alex strikes up a friendship with Dr. Kovac, perhaps trying to get him and his mother together.
    • Carol and her teenage lab partner when she's taking pre-med.
  • In Wizards of Waverly Place this is Alex and Mr. Laritate in the third season. Also, Justin and his peers.
  • In an episode of Yes, Dear, Greg's 65 year old father has recently retired and gotten into Superman comics. He goes to a comic book convention and runs into his internet buddies, who are all no older than 12.
  • Steven Hyde and Leo in That '70s Show are a prime example of this. Aging 60's hippie meets teenage burnout.
  • Spencer and Sam on iCarly.
    • ALL of Spencer's friendships except T-Bo and, arguably, Socko. This is commented on regularly (and was even an episode premise).
  • It's Always Sunny in Philadelphia: Frank Reynolds is old enough to be the father of the other main characters (and kind of is in the case of Dennis and Dee) but is considered one of the Gang.
  • Sikowitz from Victorious acts more like a friend than a teacher towards his students in many episodes, as he also helps them with personal problems or even pulls pranks on them
  • Goomer and Dice from Sam & Cat have an age difference of 15 years and therefore also qualify. It is even implied Goomer is Dices best friend
    • though mentally, Goomer acts much younger than his actual age
  • around 16-year-old Max from The Thundermans states multiple times that around 43-year-old Dr. Colosso is his best friend. Colosso calls him the "evil son he never had"
  • One episode of Being Human saw Mitchell befriending a boy who was their neighbor, protecting him from bullies and hanging out with him. The boy's mother is initially glad that he is being so nice, but things turn south when she catches the boy watching a vampire snuff film he got from Mitchell (Mitchell offered to loan the boy any of his Laurel and Hardy DVDs and forgot that he hid the snuff film in one of the cases). Cue accusations and a massive Pædo Hunt, which the boy tries desperately to put an end to. It doesn't end well for anyone.
  • Blair and housekeeper Dorota on Gossip Girl.
  • In an episode of Kate & Allie, Chip befriends Louis, a mentally handicapped and good-natured homeless man who appears to be the same age as his mother Allie. Kate and Allie initially hear Chip tell about his exploits with Louis and assume that Louis is another child, but later learn his true age when they find him in their house in the middle of the night after Chip invited him in so that he would have a place to sleep. Louis reappears in a few more episodes and his friendship with Chip continues.
  • Super Sentai has done this several times. Examples include Nozomu (10-11 years old) and Alata (21 years old, according to Word of God) in Tensou Sentai Goseiger; and Kou (9) and Lin (18) in Gosei Sentai Dairanger. The latter overlaps with May–December Romance since the show's epilogue implies they married or had a romance later on.
  • In an episode of Step by Step, we meet the twentysomething Cody's longtime best friend who's a middle aged man.
  • On The Young and the Restless, the rich and elderly Katherine is best friends with the decades younger former stripper Nikki.
  • In Merlin, the elderly physician Gaius is friends with a lot of much younger people, particularly Guinevere. (Merlin himself belongs in the Like a Son to Me category, and he's technically employed by Arthur).
  • Walter with Olivia and Astrid in Fringe.
  • Appears on The West Wing as the characters are True Companions and their ages span from early twenties to late fifties. The two friendships that stand out are The President and Charlie, and Leo and Josh.
  • Zuri and Nana Banana in Jessie is about as big of an age gap as you can get. A 7 year old with a woman old enough to be Great-Grandmother when you consider the actual age of both actresses.
  • In Modern Family, Luke (who is 11 years old) becomes friends with the grumpy old neighbor (who apparently fought in World War II).
  • JAG: Harm and his late father's wingman Tom Boone.
  • Arrow:
    • Tommy Merlyn and Thea Queen had this, owing to Tommy being best friends with her brother before he went missing; she had something of a crush on him and he acknowledged that she was an attractive young woman, but they remained merely good friends. After his death, she would find out he was her half-brother, making it Heartwarming in Hindsight....and also a little squicky.
    • On the island, Oliver became good friends with Slade Wilson, a man at least a decade older than him, due to a mutual reliance on one-another. It unfortunately ends tragically.
    • Oliver seems to have stricken one up with Roy Harper as well, due to Roy's Hero Worship of Oliver's alter-ego. When Roy is given super strength that come with mental issues, Oliver steps in to try and help him with it, and while the two have problems, Roy becomes the fourth person Oliver intentionally revealed his identity to, and once cured of Mirikuru, eventually becomes his sidekick.
    • The sister Series Legends of Tomorrow has Firestorm's two halves. Dr. Stein is at LEAST twice as old as Jax. And while they do need to physically be around each other every now and then to survive, they both like and willingly talk to/hang out with the other. Jax also ends up having it with some other members of the cast, like Captain Cold.
  • One Tree Hill has several examples, such as Whitey with both Keith and Karen, Chase with Chuck, and Jamie with Quentin, as well as with his honorary family members, Brooke, Julian, and Skills.
  • Gotham: When Barbara comes home after a few weeks to find Selina Kyle and Ivy Pepper squatting in her apartment, she just shrugs and starts chatting amicably with them. Later, they're seen helping her pick out a dress, and she in turn helps them with their minimal dating lives.
  • Marco (Gepetto) and Archie (Jiminy Cricket) in Once Upon a Time, but not in the way they appear. Gepetto is an old man and Jiminy looks like a man in his late thirties/early forties, but it's later revealed that when they met, Gepetto was a little boy and for reasons too complex to get into here, Jiminy hasn't aged since that day. He's actually several decades older than Gepetto despite looking young enough to be his son.
  • In one episode of Quantum Leap, Sam Leaps into Jimmy, an adult with Down's syndrome who lives with his brother's family. Jimmy and his young nephew are best buds and share a set of bunk beds. Also, Sam's own closest friend Al is more than a decade older than him.
  • In Korean variety show Running Man, the main cast have varying ages: from late twenties (Kwang Soo), thirties (Jong Kook, Gary, Ji Hyo, Haha) and forties (Jae Suk, Suk Jin).
  • The Flash (2014): There are elements of Parental Substitute and Like a Son to Me to varying degrees in each relationship, but Harrison Wells explicitly refers to Barry, Cisco and Caitlin as his closest friends. (It's likely that they're also his only friends, as he has no social life outside of STAR Labs due to being a pariah to most of the city.) All three of them are in their twenties and, although his age is never stated, Harrison is either in his forties or very early fifties. (His actor, Tom Cavanagh, was 50/51 at the start of the series, and is Older Than He Looks.)
  • In Oshin, the then-seven year old protagonist's first actual friend was an already adult deserter of the Imperial Japanese Army, Shusaku, who saved her from dying in the snow, let her stay in his hut, and taught her how to write and read. Unfortunately, Shusaku was eventually caught by the Army and promptly executed for desertion.
  • Verano Azul is about the friendly bonds developed between Chanquete (50/60's), Julia (probably late 30's/early 40's), and a bunch of outsider kids (more or less in the 7 to 14 age range)
  • The OA has Prairie (28) and Betty (somewhere in her 40s) forming a strong bond with four teenage boys — Steve, Jesse, French, and Buck — as Prairie tells them all her life story. Deconstructed because people keep jumping to the conclusion that something inappropriate is going on, being unable to think of a non-creepy reason for grown women to spend so much time with high school students. Betty is even forced to quit her job over it.
  • Bewitched: Darrin and his boss Larry Tate, who is at least a decade or two older than Darrin. Darrin usually goes to Larry for marriage advice, since he has far more experience in that field.
  • Thelma and Iola in Mama's Family. Iola is about the same age as Thelma's son.
  • In Supergirl (2015) season 3, Alex (who's always wanted kids) forms a bond with Sam/Reign's teenage daughter Ruby. In the episode "Fanatical", a subplot has Alex trying to help Ruby through her grief while J'Onn is trying to help his father with his illness. After a trip to the arcade goes very wrong, Ruby and the millennia-old Martian are able to talk to each other instead.
  • Switch (1975): Frank MacBride is a retired cop in his sixties. His partner Pete Ryan is about 25 years younger, going by the actors' ages. In "Stung from Beyond," the two even go undercover as a father and son.
  • Good Omens (2019): Anathema (mid-twenties) and Adam (just barely eleven) take to each other like a house on fire. They meet when he overhears her crying, he approaches her to see what's the matter and if there's anything he can do to help. She tells him there's not, but she clearly appreciates the gesture and invites him inside for a snack. Adam inquires if the rumor that Anathema's a witch are true, and she replies that no, she's an occultist. She then shares some of her occult magazines with him, which he finds utterly fascinating, and soon, he introduces his other friends to her, too. (They're all allegedly against "witches," but it's pretty clear they all think the idea of a witch living next door is awesome.)
  • The Twilight Zone (1985):
    • In "Paladin of the Lost Hour", there is a more than thirty year age gap between Gaspar and Billy Kinetta but they quickly become very close friends.
    • In "Extra Innings", the down-and-out baseball player Ed Hamner, who is his late 30s, is good friends with his 12-year-old neighbor Paula, a huge baseball fan who idolizes him.
  • Intergenerational relationships are a major theme in The Noddy Shop. For instance, the children are friends with Aunt Agatha, the sister of their grandfather Noah.
  • Downplayed on Young Sheldon. Sheldon Cooper is a nine-year-old boy in high school and befriends a student named Tam Nguyen. Tam's age is never given, but he'd be at least five years older than Sheldon. Tam also occasionally hangs out with Sheldon's twin sister Missy and their neighbor Billy Sparks, who's the same age as Sheldon and Missy.
  • In Parks and Recreation, April is significantly younger than the rest of the major characters, and started out at the Parks Department as a college intern while the rest of them were mid-career adults (or nearing retirement in the case of Jerry). Lampshaded in a story arc where Ben and April go to DC to work on a congressional campaign, and all the other staffers assume she's his daughter.
  • The Neighborhood: Calvin and Tina Butler are in their fifties. Dave and Gemma Johnson are in their late thirties/early forties, not much older than the Butlers' sons Malcolm and Marty, who are also friends with the Johnsons' ten-year-old son Grover.
  • Devs: Lyndon and Stewart seem to be inseparable while working on the Devs project in spite of Stewart being elderly and Lyndon being 19. Lyndon is even played by a young woman to make him seem even younger. An early scene has Stewart grousing that people in Lyndon's generation have no culture.
  • Only Murders in the Building: Charles and Oliver are both over forty years older than Mabel, but the three bond over their shared interest in True Crime, and their collective suspicion that a suicide that occurred in their apartment building was actually a murder. Mabel snarkily lampshades it, asking Charles "how invested" she should get in them, since he and Oliver are both quite old and she doesn't want to get attached to two men who might die soon for the same reason she wouldn't adopt a twenty-year-old dog. They all become close anyway.
  • LazyTown: Sportacus and Stephanie have this, with the former being an adult and the latter being a tween. They met after she contacted him for help and soon bonded thanks to their mutual athleticism and perkiness.
  • Last of the Summer Wine has several:
    • The Trio generally have this sort of rapport with Sid from the Cafe, partly because they always go there and partly because Sid gets bored easily.
    • When Tom Simmonite stops hanging out with Truly and Clegg, he befriends Smiler who is his co-worker in Auntie Wainwright's Shop.
  • Queen Sugar: Ernest Bordelon and Remy Newell, who are appropriately aged to be father and son. Charley is initially surprised when she meets Remy because she expected him to be much older.
  • The Full Monty (2023): School caretaker Dave befriends Dean, a 12-year-old student, after he finds the boy has been nicking food from the school kitchen. Dave even stands up for the boy after witnessing him being bullied.

    Music 
  • In "Cory's Coming" by Harry Chapin, a young man frequently visits Old John Joseph.
  • "Clair" by Gilbert O’Sullivan. He wrote the song about the young daughter of his then-manager, whom he often babysat. It’s actually a lot less creepy than it sounds.
  • "Better People" by India Arie. She basically sings that if people would connect with other people older and/or younger than them, the world would be better off.
  • Elizabeth Darcy and Mr. Woodhouse in the Mr. and Mrs. Darcy Mysteries.
  • An early David Bowie song "The Little Bombadier" is all about this trope, including the (incorrectly) sinister interpretation of those observing the events.

    Podcasts 
  • Unwell Podcast: Dot Harper and Wes.
  • Wooden Overcoats:
    • Georgie's in her early twenties or so, and Mayor Desmond is at least sixty, likely a little older. However, the two have become good friends since she started working as his assistant, to the extent that she stands up for him at his wedding.
    • In "Rudyard Takes a Hike," the titular character (about thirty-five) bonds with and becomes protective of the ten-year-old Calliope, because she reminds him of himself when he was a child: isolated and teased, with an interest in death that others find off-putting. He jumps to her defense a number of times, and after she's eventually accepted by her peers and made troop leader, she invents a badge just to award to Rudyard as a show of her appreciation. At the end of the episode, Calliope also gets on with Rudyard's twin sister Antigone.

    Pro Wrestling 
  • Invoked with CMLL's Torneo Gran Alternativa, which was put in place to cultivate these kinds of friendships by requiring wrestlers of different generations to tag\pareja if they want to enter. Although it also allows successors and predecessors of a gimmick to team up as well.
  • Happens often with mentor/student storylines.
  • Ric Flair and Triple H have a 20 year age difference. Their hanging out together backstage led to the creation of the group, Evolution.
  • Ivory and Molly Holly, who are 16 years apart, but have been close friends since Molly came to the WWF in 2000. They regularly traveled together, did the "Kickin' Ass For Gas" tour in the indies in 2006 (the gimmick was they were trying to earn enough money to get to Trish Stratus' wedding) and when Ivory went into the WWE Hall Of Fame in 2018, she chose Molly to give her induction speech.

    Radio 
  • Adventures in Odyssey has many of these.
    • John Avery Whittaker is veritably the oldest character in the show, and yet forms friendships with many of the other characters. The closest of these are likely his relationships with Connie Kendall and Eugene Meltsner, who began the show as both high school and college students, respectively.
      • Whit is also trusted by most, if not all, of the kids who come into Whit's End each day.
    • Bernard Walton and Eugene also form a close bond, particularly after the revelation that they are distantly related. This is especially showcased in the episode "First-Hand Experience", the beginning of their Road Trip saga.
    • Jason Whittaker (Whit's son) and Jack Allen (Whit's childhood friend) have a clear friendship from their first on-air meeting in Album #22. Due to their being created as two different sides of Whit's character, however, their bond is somewhat strained by their disagreements about taking action or risks (which comes to a head in the "Darkness Before Dawn" saga).
    • Wooton Bassett is "a man in his thirties" who never grew up. He forms friendships with many of Odyssey's kids, particularly Grady.
  • Our Miss Brooks
    • Miss Brooks' best friend and confidante is her landlady Mrs. Margaret Davis. Mrs. Davis states a few times that she is "sweet sixty" (i.e "The Big Game"). Miss Brooks is hinted to be in her late twenties in several episodes of the program.
    • Miss Brooks is friends with sixteen-year-old Walter Denton, and, to a lesser extent, Harriet Conklin and Stretch Snodgrass. However, Miss Brooks herself would surely object to the label!

    Theater 

    Video Games 
  • Pokémon Ruby and Sapphire: In both the originals and the remakes, the 10-year-old Player Character actually befriends Maxie and Archie — the leaders of Team Magma and Team Aqua respectively — after their Heel–Face Turn. The latter is especially buddy-buddy with the player even as the antagonist, and the former is fairly courteous as well. Even in Pokémon Ultra Sun and Ultra Moon the two are fairly decent towards the 11-year-old player, all things considered.
    • Pokémon Scarlet and Violet: Because Naranja/Uva Academy allows people of many different ages to enroll, there's no clear ages to the main cast. However, from the three friends the protagonist makes, only Penny is around their same age, while Nemona and Arven are clearly older. Arven even reffers to the main character as his best friend. In the DLC the protagonist also befriends Kieran and Carmine. While the former is around the same age, the latter is his older sister.
  • The Legend of Zelda:
  • Metal Gear:
  • BioWare and this trope are good friends:
    • The Player Character and Mission in Knights of the Old Republic (technically, Mission and everyone), as well as Jolee and everyone.
    • Mass Effect:
      • Shepard and Tali, and Shepard and Liara. In fact, for Liara and Shepard it is both ways. Liara is 106, the asari equivalent of being barely out of her teens, and Shepard is in his/her early thirties. Anderson and Shepard also are like this, with Anderson being 46 in the first game.
      • Wrex from ME1 and Samara from ME2 (both roughly 1,000 years old) also count. The Shepard/Anderson friendship also has as Anderson acting as a father figure to Shepard. Joker (late 20s/early 30s) and Dr Chakwas (late 50s/early 60s at the youngest) seems similar.
    • Dragon Age: Origins:
      • Alistair and Wynne have a warm, somewhat flirty relationship with May-December subtext, though remains platonic.
      • Wynne also counts with Leliana and the Warden him/herself (who is usually stated as being relatively young). Though his age is not clear, Sten and the Warden may also count.
  • Kingdom Hearts:
    • Sora's constant companions Donald Duck and Goofy are more or less adults, though this is a little obscured with them being anthropomorphic animals. Although his strongest feelings are for Riku and Kairi, who are his age.
    • The games also have a similiar friendship between Riku and Mickey.
    • Axel's friendship with Roxas, as Axel is an adult and Roxas is in his early teens. His relationship with Roxas and Xion is very like this in 358/2 Days, with the two both looking at Axel kinda like a big brother for his knowledge on the opposite sex, emotions, relationships... he in turn is very protective of them, and his anger at being forgotten makes a lot more sense considering this.
    • And again with Aqua, Ventus and Terra, which is all the more symbolic, considering the Theme Naming going on, and the fact that Ven' heart is sleeping inside Sora, and Terra and Aqua are the ones who chose Riku and Kairi to be the next Keyblade wielders (accidentally so in Aqua and Kairi's case).
  • Tales of Symphonia: 17-year-old Lloyd's best friend is 12-year-old Genis. During the game he also makes friends with Zelos (21) and Regal (32). And to really screw with your head, Presea is biologically and mentally twelve, but chronologically twenty-eight.
  • In Tales of the Abyss, this is pretty much true for Jade (mid-thirties) and the entire rest of the party, who are in their teens (except for Guy, who's in his early twenties). It's the most pronounced with Anise, who is thirteen and is frequently paired up with him when the party splits up in cutscenes and plot events.
  • Tales of Vesperia (noticing a theme here?) does this too; Karol (12) strikes up a good friendship with most of the party, but in particular his guild subordinate (and main protagonist) Yuri (21), who calls Karol 'Boss'. With one exception, none of the playable cast is over 21; that exception being Raven, who at 35 gets the somewhat sarcastic nickname "Old Man".
  • Tales of Xillia has the largest age gap so far if we're going by human years with the Elize as the youngest at 12 and Rowen as the oldest at 63. The age gap is large enough that he's old enough to be a grandfather to three of the party members and father to the other two since the next oldest is Alvin at 30.
  • Several examples are possible in the Fire Emblem series, thanks to the support system.
    • Fire Emblem: The Sacred Stones has, among the more notable ones, Amelia (~15) and Duessel (old enough to be her grandfather, likely in his mid 50's), who even get a double-ending where Amelia becomes Duessel's "most trusted companion". The fact that Duessel reunites Amelia with her Missing Mom Melina, whom he rescued from the bandits who kidnapped her when Amelia was a child, probably helps a lot. Duessel also has good relationships with Ephraim (around early 20's), Cormag and Knoll (both in their mid 20's). Ewan (13-14) and his magic teacher Saleh (age not stated, but most likely in his mid to late 20's) also get a double-ending. There's also Gilliam (likely around his late 30's) and both Franz and Neimi (around Amelia's age, if not slightly older, who also has one with Garcia).
    • Blazing Blade has Serra (a 16 year-old cleric) and Oswin (a knight in his mid 30's), albeit they can also become a couple. Canas (probably in his late 20's or early thirties) also develops one with Nino, who is 14.
    • In Fire Emblem: Awakening, there's Gregor (a mercenary in his 40's/maybe even 50's) and either Lon'qu (early-to-mid 20's Master Swordsman) or Ricken (a pre-teen/early teenage mage).
    • In Fire Emblem Fates, Yukimura (a Badass Bookworm implied to be in his early 40's) has this with Sakura (a White Magician Girl in her early-to-mid teens tops). In one of the DLC stages she tells him that she misses Hoshidan dango, so he outfits one of his Automatons to make her some.
    • Garreg Mach Monastery in Fire Emblem: Three Houses generally houses students from ages 15 to 18 in the same class, but there are a few students who are much older, with the most stand-out example being Balthus (26) having a support with Lysithea (15), despite being over ten years her senior. Hanneman, a teacher at 51 years old, also has this dynamic with every student and even some teachers, including the protagonist.
      • Another example from the same game is Annette and Mercedes, who are 16 and 22 respectively at the beginning of the game. They're best friends and are established to have known each other for a couple years prior to enrolling at the Officer's Academy.
  • Princess Maker 2
    • The main character's daughter can have these dynamics with... a centuries-old dragon who lives in the desert. The dragon is an old friend of the girl's father figure, back when he was a wandering warrior, and being a Chivalrous Pervert as well he endlessly teases the girl about her figure (and can give her the Dragon Tights, one of the outfits required for the dancing competition in the Harvest Festival).
    • Additionally, the dragon has a young and reckless grandson. If the heroine beats said grandson in battle when she's older than 15, the young dragon falls in love with her and the old one can give the main character the chance to have their kids engaged. It's interesting to point that said dragon is one year younger than the main character.
  • Mother:
  • Chopin and Polka in Eternal Sonata. They're so close that fans try to pair them together even though Polka's twenty-five years younger than him (and officially paired with Allegretto).
  • Namco × Capcom:
    • Felicia and Klonoa are made of this. She is a Catwoman who's somewhere in her late teens or early 20s, while he is a Kaze no Neko ("Cat of the Wind") in his early to mid teens. Both of them are cheerful, positive and playful people who decided to be friends and stick together just because both of them are cat people with long hair.
    • Much for King's wall-banging despair, they try to make him join their group, no matter how many times he tries to explain them that he's just a short-haired human Luchador wearing a jaguar mask.
  • Professor Layton, especially in Professor Layton and the Unwound Future, features Layton (34/35 in the prequels, 37 in the sequel/main trilogy) and Luke's (10 in the prequels, 13 in the sequels/main series) friendship. Unwound Future features a statue of a man with a top hat resembling Layton, and a young boy who looks like Luke, and the story on it describes a similar friendship between an author and a sick young boy until the boy died of his illness.
  • Sengoku Basara has several examples. There's Masamune (19) and Kojuro (30ish), who are sometimes joined by Itsuki (12); Yukimura (17) and Sasuke (mid 20s); Ieyasu (15) and Motochika (20s); Yoshihiro (60s/70s) and Keiji (22); and Mitsunari (19ish) and Yoshitsugu (prob 30s).
  • Touhou Project:
    • Yukari and Yuyuko, the former several millenia-old at the very least and the latter (originally) an ordinary human. Even after Yuyuko has spent about a thousand years as a Cute Ghost Girl Yukari is still many times her age and outclasses her in every way possible, but they remain close friends.
    • Yukari also has a Vitriolic Best Buds-style relationship with Reimu, who still is human and whose age is a double-digit number. Frankly, most youkai with human friends are like this.
  • Kraden is friends with all of the player characters (most of whom are Kid Heroes) in the Golden Sun games. Piers may or may not be Really 700 Years Old, so his friendship with Felix's group likewise fits the mold— in fact, he says that he'd rather not admit his age so it doesn't affect how they see him. Obaba becomes friends with the heroes of The Lost Age and Dark Dawn, as does her baby great-grandson Eoleo (on the younger end of the relationship in TLA, and the older end of the one in Dark Dawn).
  • Persona 3 is full of these with both the male and female protagonists. This is the case for Tanaka, the Devil Social Link, the elderly couple (Mitsuko and Bunkichi), who have the Hierophant Social Link, and Mutatsu the monk, who serves as the Tower Social Link, but also with Maiko, the Hanged Man Social Link, who is an elementary school student in comparison to the protagonist (a junior in high school), and your mutual friend Sun Social Link Akinari Kamiki, a writer in his twenties. In addition, party members 10 year old Ken Amada and 18 year old Akihiko Sanada become good friends over a mutual love of beating things up.
  • Persona 4:
    • Alongside the main character's younger cousin Nanako befriending the rest of the party, we have the MC and the persons holding the Death (a widow in her 60's), Temperance (a stepmother in her early/mid 30's) and Devil (a Hospital Hottie in her late 20's) Arcana Social Links. They're also seen in The Anime of the Game, but they're Out of Focus.
    • The Updated Re-release Persona 4 Golden adds Adachi, a bumbling twenty three year old police officer, as a Social Link of the newly-introduced Jester/Hunger Arcana.
  • Ib has the titular Ib, a nine year old girl, and Garry, who seems to be a young adult. The two become good friends due to having to work together to survive being in a really strange art gallery.
  • In The King of Fighters there are several examples:
    • The Japan team is formed by Kyo (20), Benimaru (21)... and Daimon (29). The latter started as more or less the mediator between the two others, then they became True Companions.
    • Also K' (age unspecified, but seems to be 18 tops) and Maxima (29). As well as Kula (14) and Chin (mid 80's); this one was lampshaded when Kensou (who's 19 by the way) mistakes them as having a May–December Romance.
    • This trope becomes a huge plot point in the Tales Of Ash saga. 16/17 years old Ash Crimson had this with 27-year-old Elisabeth Blanctorche, who doubled as his Only Friend. So to protect the only person he truly loved and cared about, Ash staged a massive Batman Gambit that involved attacking and depowering both Chizuru and Iori, making himself the most hated fighter all around and go against everyone and everything he knew... to keep Elisabeth safe and make sure she won't have to fulfill her destiny to fight the current Nebulous Organization, Those of the Past. So yeah, for his much older friend, Ash staged the whole last arc and ended up ret goned. It's lampshaded by Kim in XIII, even: if Kim fights Ash he will refer to Elisabeth as Ash's "guardian" and ask him to return to her side, threatening to drag him back by force if needed; Ash will not just refuse to leave, but he will correct Kim on how "Betty" isn't his caretaker.
    • Also the Ikari Warriors Ralf (39) and Clark (34) are much older than their fellow fighters/mercenaries Leona (19) and Whip (16-17 apparently), but the four have extremely strong bonds and both Ralf and Clark treat the orphaned Leona like a younger sister (in addition to her being the adoptive daughter of Heidern, their boss.)
    • The Psycho Soldiers team is formed by Athena and Kensou (both around 18 years old) and their master Chin (an old man). Later on they are joined by Bao, who is 12.
  • In Borderlands 2, Tiny Tina, a troubled and demented thirteen-year-old Demolitions Expert, has this with Roland (somewhere in his 30s), Brick (around the same), and Mr. Torgue (in his 40s). Roland serves as a Parental Substitute, while Brick and Mr. Torgue are enablers to her love of explosives and bringing destruction upon the bandits of the waste. In the Tiny Tina's Assault on Dragon Keep DLC, Lilith plays the role of a Cool Big Sis to Tina while Mordecai simply just puts up with her (though they bond over the fact that they both love the same show).
  • The Sonic the Hedgehog games have a few examples:
    • Downplayed with Amy and Cream, as they are both children, but still present as Amy is twice Cream's age (Amy is twelve, and Cream is only six).
    • Sonic and Knuckles are also this for Tails. Him being 8 and Sonic and Knuckles being 15 and 16 respectively, according to the manual of Sonic Heroes.
    • In Sonic Rush, the 14-year-old Blaze eventually befriends Cream as well. The sequel also introduces Marine, who's seven.
    • Team Chaotix consists of the 20-year-old Vector the Crocodile, the 16-year-old Espio the Chameleon, and the 6-year-old Charmy Bee.
    • Most of them are like this with the Mario cast in the Mario and Sonic series. Mario is in his mid 20s (and Yoshi's Island DS shows most of the cast were babies at the same time) while most of the Sonic gang is in their teenage years, but the cast sees each other as friendly rivals. Perhaps the only exceptions are Bowser and Dr. Eggman.
  • Swaine to Oliver and Esther in Ni no Kuni. Oliver is about twelve and Esther is about fourteen. Swaine is about twenty-five to thirty ( judging from the fact that when the party meets his younger self fifteen years in the past, he looks slightly younger than Oliver), but looks even older due to his extremely unkempt appearance.
  • Clementine from The Walking Dead (Telltale) mostly has parental figures in the first season, most notably Lee (with the possible exception of Ben, who's about six years older than her) but in the second game her relationship with Luke and Nick takes place on far more equal terms. She actually spends a lot of time parenting Nick, who's likely well into his twenties. In season three, with Clem now 13, she develops a close friendship with the Player Character Javier García, who is in his early to mid 30s. In season four, 16-year old Clem gets to be the older part of such dynamic for the first time, due to her close bond with AJ, who's 5.
  • Tomodachi Life doesn't really have an age distinction beyond "adult" and "kid". That being said, an Adult Mii and a Kid Mii can develop a friendship, or even become best friends.
  • Possible (like over half tropes) in the Sims series games. In The Sims 2 only the family you're playing ages, and thus a friendship between two people of the same age can become intergenerational and viceversa so maybe not really this trope. The Sims 3 premade examples of this include River McIrish (teen with 5 - out of 14 - days to young adult) and Claire Ursine (adult\middle aged with 16 - out of 21 - days to Elder), and (Ambitions expansion pack) Jade Greenwood (teen with 14 days to young adult) and Silver Racket (adult with 13 days to elder).
  • In most Harvest Moon games, you are a 20-something year old who can befriend people of various age groups.
  • Xenoblade Chronicles:
    • Xenoblade Chronicles 1: Riki is a 40 year-old Nopon with eleven children who becomes friends with everybody with the party whose ages range from 18 to 27, and was already previously acquainted with Melia. Played With with Melia herself as while at 88 years old, she is by far the oldest member of the group, she is a Half High-Entia meaning she ages and matures more slowly and as such, has the same level of maturity and experience as her younger companions.
    • Xenoblade Chronicles 2: 15 year-old salvager Rex is shown to have long been friends with Azurda, affectionately known as "Gramps", who, as a Titan, has been alive for several centuries. He also later becomes friends with Mòrag, Zeke and Nia; the former two of whom are at least ten years older while Nia is possibly centuries older as a result of being a Flesh Eater Blade.
    • Xenoblade Chronicles 3: As Kevesi and Agnians in the world of Aionios do not live younger than ten years, the Nopon companions Riku and Manana are automatically this to the Ouroboros group despite their unknown ages. And given Riku's Mysterious Past, he is possibly centuries old or older than Aionios itself.
    • Xenoblade Chronicles X: Lin (13) with most other characters by virtue of being the youngest human not in stasis by several years. Most notably with Elma (29) true age unknown but likely much more than that as it is stated that 29 years ago was when she first came to Earth rather than when she was born.
  • In The Last of Us, Joel is a grizzled survivor in his 50s who befriends the 14-year old Ellie over the course of the game. There's also Joel and Henry, who's 25.
  • The Last of Us Part II: Ellie, now 19, befriended Joel's brother Tommie and his wife Maria, both about Joel's age. Her girlfriend, Dina (also about 19), seems to be friends with a majority of kids who live in Jackson. Dina herself used to be friends with a man named Eugene (he's a Posthumous Character, but he was probably about 50-60). There's also Abby (likely early twenties), who befriends Lev (13).
  • Overwatch has the grubby Aussie criminals Junkrat at 25 and Roadhog at 48.
  • Wataru ends up striking a meaningful friendship with Ange in Super Robot Wars X. He even becomes Ange's Morality Pet. Ange says more than once that she just can't say no to him. Moments just after he shows up Lelouch practically becomes the Cool Big Bro and Big Brother Mentor that Ange needs and deserves to have. Ange's interactions with both Wataru and Lelouch play a role in making her character more benevolent and reasonable. So much that when she finds Sylvia walking on her own, she offers her a hand to restore order to Misurugi and establish Cafe Ange in her old home.
  • In Battle Fantasia, Marco (age 9) and Cedric (age 16) end up becoming friends. Granted, this is mostly one-sided on Marco's side and Cedric mostly finds him annoying and is following him around because he can't, in good conscience, leave a kid alone. However, by the end of Cedric's story mode, he acknowledges he ended considering Marco a friend and even decides to become his Magic teacher.
  • Red Dead Redemption 2: Most of the Dutch Van Der Linde gang members are friends, spanning from middle-aged men like Dutch and Hosea to even children like Jack Marston.
    • "The Veteran" Stranger mission involves the 36-year-old Arthur Morgan befriending an elderly Civil War veteran named Hamish, who (despite having a prosthetic leg) never lets anything bad get him down. The two bond over chatting, finding Hamish's horse Buell, fishing for muskies, and hunting wolves. Sadly, things come to an end when Hamish gets gored to death by a massive wild boar, but Arthur shoots the boar in the end, remarking "We got him, old man."
    • Relating to "The Veteran", the same thing can happen with John Marston if he finishes "The Veteran" for Arthur (or if Arthur never met Hamish at all).
  • Ivor and Jesse in Minecraft: Story Mode. Though Ivor (previously a member of the legendary Order of the Stone) began the series as the antagonist, he has a Heel-Face Turn and helps Jesse defeat the Wither Storm. By Episode 5, he is a prominent member of the group, and his friendship with Jesse develops over the remainder of the season. When he returns as a ninja in Season 2, you have the option to hug him.
  • Road To Guangdong revolves around the player character, a young girl in her early-20s, and her relationship with her grandaunt whom she barely knew until she needs to chauffer the latter to a cross-country funeral. Much of the game revoles around their developing friendship while the player goes on a journey of self-discovery along the way.
  • In World Neverland, it's possible for a child character and an adult character to become friends. However, they can't max out their friendship and become Best Friends, as the adult will tell the child to wait until they're older. If the child character grows up and then becomes Best Friends with their adult friend, they'll even have special dialogue acknowledging how glad they are that they can finally be good friends with their adult friend.
  • Player Character V (27), from Cyberpunk 2077 gets to befriend quite a lot of older characters, due to this being a universe with advanced rejuvenation treatments and aesthetic implants. Most notably, the fixer Rogue and The Rockstar Kerry Eurodyne, both about 70-80. They also start off as friends with their ripperdoc, Viktor, who is about 60. There's also Takemura, who looks to be about 50-60, and might possibly be older.
  • Yakuza 3 has a quite sweet example between 8-year-old orphan Izumi and twenty-something yakuza lieutenant Mikio. The two meet when Mikio's yakuza family try to shut down the orphanage Izumi lives in, and bond over a mutual love of dogs, eventually taking in and caring for a stray puppy together.
  • Skullgirls:
    • Played with when Annie and Beowulf become friends at the end of their story arcs, but the intergeneration aspect is the reverse of what it looks like. The public sees Annie, a 15-ish actress, befriending Beowulf, a 37-year-old pro wrestler, but Beowulf is a mortal man, and Annie is very, very much the elder of the two.
    • At the end of her story mode, Umbrella (age 11) has become good friends with Filia and Painwheel (both around 16).
  • My Time at Portia has the elderly scholar Isaac and Polly, a studious young girl and the middle child of three sisters, who are best friends due to their common interest in historic literature and the game Cross Five.
  • Mr. Saitou: Brandon, a curious and outgoing child, and Mr. Saitou, a weary middle aged salaryman, become good friends over the course of their adventure in the dream world. The ending scene implies it may not have been a dream and they became good friends in real life.
  • Final Fantasy IX: Steiner (33 years old) doesn't have very good relationships with most of the cast, due to his uptight Lawful Stupid attitude. One of the few exceptions is Vivi (physically 9 years old, chronologically 6 months old), whom Steiner deeply respects.
  • Final Fantasy XII has a Villainous Friendship example between Dr. Cid, who's 58, and Vayne, who's 27.

    Visual Novels 
  • Ace Attorney has quite a few examples.
    • The biggest being Kay Faraday (17) and Dick Gumshoe (32), who end up acting like children when the other is around (they first met at 10 and 25, respectively). To an extent, Edgeworth (26) and Kay, Phoenix and Maya (24 and 17 when introduced), Nick and Pearl (8/9) and Gumshoe and Maggey (22/23) all count as well.
    • Machi and Lamiroir in Apollo Justice: Ace Attorney, although that one's more like a case of Parental Substitute.
    • The Judge seems to develop, over time, an odd friendship with much of the main cast (especially Phoenix, as seen in Apollo Justice.) That doesn't stop him from giving you penalties, though - work is work.
    • Dual Destinies shows that 21-year-old Simon Blackquill and 11-year-old Athena Cykes used to have this years ago, before things went From Bad to Worse for them. Though they might have retaken it in the Good Ending, where 28-year-old Simon is saved from being unfairly executed much to 18-year-old Athena's joy.
  • Shirou and Ilya in Fate/stay night. In appearance. In reality, the age difference is less than five years, with Ilya being the older one. There are some pretty twisted reasons why this whole situation came about. Their relationship is very much that of the brother and sister kind; ironically, Shirou's adopted father Emiya Kiritsugu is Ilya's biological father, making them actual siblings by adoption. Ilya appears to be aware of this from the start, Shirou only learns of it in one route.
  • Narcissu ~ Side 2nd: Setsumi (15) and Himeko (23). The trope is invoked in this case, as Himeko was trying to finish the list of the 10 things that she wanted to do before her illness killed her, with one of the items being that she wanted to become friends with somebody significantly younger than herself. This trope applies even more with regards to Himeko and "Nello" in flashbacks, although the other girl's exact age is never given.
  • Spirit Hunter: NG:
    • Ami is good friends with Yuri and Kaoru, despite her being elementary-aged and them being high-schoolers. This is explained as Ami and Yuri living in the same apartment building, with Yuri playing with Ami when Ami's mother was too busy with work to look after her.
    • While Akira's first two companions are both around his age, the second set are Ban and Rosé, a middle-aged man and a woman who keeps her age a secret, but frequently teases Akira for being young and 'cute'. Having adults who're experienced with supernatural affairs proves very useful to Akira, though that doesn't stop him from bickering with them like he does with his high-school friends.

    Webcomics 
  • Batman: Wayne Family Adventures: Due to the sheer weirdness of the Wayne family (being superheroes and all), a lot of the Bat kids have friends/honorary family members who are several years older than they are. One example would be Harley Quinn and Poison Ivy. Both women are well into their thirties (Ivy was an effective villain back when Dick was still Robin), yet the episode "Branching Out" shows them becoming friends with Spoiler and Orphan (both of whom are in their teens).
  • Riff and Dr. Schlock from Sluggy Freelance (in their late 20's and late 80's, respectively) bond over their shared love of Mad Science.
  • Pandora (old even for an immortal) and Sarah (18) from El Goonish Shive. To a lesser extent, Mr. Tensaided (somewhere in his thirties or forties) and Sarah, courtesy of Magickal Gatherings.
  • Alcolla (preteen) and Yakuv (unspecified, but at least mid-30s) in Reliquary.
  • Julian Sands (adult camel) and Jarrad Dryandra (numbat child) in Doc Rat. Their friendship comes under scrutiny when Julian comes out of the closet.
  • Bob (probably in his twenties) and the elderly Mrs. Primrose in The Inexplicable Adventures of Bob!.
  • Richard and Cale from Looking for Group. Richard is apparently hundreds of years old.
  • In Aki-chan's Life (which is the sequel to the above mentioned fan fiction The Second Try) the titular Aki Ikari and former pilot Rei Ayanami are best friends, despite (or perhaps, because of) the big and weird differences in age between the two.
  • In Alfdis & Gunnora Alfdis and her teacher Lord Frey appear to have as much a friendship as a Mentor/Student relationship.
  • In Girl Genius, Agatha Heterodyne and the Jaegermonsters who follow her. And possibly just about everybody with Airman Third Class Axel Higgs "the Unstoppable".
  • Many relationships in Tower of God, due to the different life spans of the races and the life-prolonging characteristics of Shinsu.
    • Kids like Khun and Hatz are in their late teens while their good friend Shibisu is in his 30s, whereas Bam is probably several hundred years old.
    • Anaak has an Odd Friendship going on with her aunt Endorsi, who is actually much younger than her.
  • The Shufflers: Märchen is in his 30s at least while Hiddenite is a young man. Hiddenite starts off being a bodyguard to Märchen, but eventually the two come to care about each other as friends.
  • Wilde Life: Oscar becomes 16-year-old Cliff's friend and Secret-Keeper after Cliff passes out on his porch in wolf form. Cliff's parents are realistically concerned that he's spending so much time with a strange adult from out of town but appreciate the positive influence on Cliff's behaviour.
    Oscar: I'm twenty-five.
    Kevin: Isn't that too old to be friends with my brother?
    Oscar: You know, I thought the same thing, but he wouldn't leave me alone.
  • In Lotta Svärd: Women of War, Taimi begins working at the Evacuation Center for the Fallen (where she cleans up corpses of dead soldiers for presentation before their burial) with an elderly man named Mr. Ritola, otherwise known as "The King of the Dead". The two of them admit to seeing each other as surrogate grandfather/granddaughter, and remain in touch via letters once the center closes down.
  • Jinx of The Whiteboard, about ten years old, is on friendly terms with pretty much the whole adult cast, and seems especially fond of Doc. (Note: the artwork can create an apparent resemblance, but Jinx, an Arctic fox, is not related to either Doc or Cara, both of whom are polar bears.)

    Web Original 
  • In the Raising Corpse skits (which feature a fictional and humorous version of the life of a young Corpse Husband), 7 year old Corpse has a surprisingly wholesome and heartwarming friendship with his babysitter's ditzy Fratbro boyfriend Kyler.
  • In Twig, Gordon, a thirteen-year-old Human Weapon, is good friends with a pair of older experiments called Dog and Catcher, and he even offers Dog a great deal of comfort just by being near him.

    Western Animation 
  • 3-2-1 Penguins!: Jason and Michelle, two seven-year-old kids, are friends with Zidgel, Midgel, Fidgel, and Kevin, who all look like they are in their thirties.
  • Adventure Time:
    • In the pilot, Finn is twelve and Jake is twenty-eight, while in the series Finn is 13 and Word of God specifying Jake is twenty-eight in "magical dog years" — which could possibly make him younger than Finn in absolute terms but he's certainly of adult age for his species. They're also adoptive brothers, Finn having been raised by Jake's parents.
    • Technically Finn and Marceline, since she's Really One Thousand Years Old (though she looks more like a teenager or young adult).
    • By the same token, Finn's and Jake's friendship with Princess Bubblegum, who is almost as old as Marceline.
    • Most recently, Marceline and the Ice King, though comparatively closer in age to each other than to the rest of the cast. It used to be intergenerational, though, when she was a 7 year old child, while Simon was 40 years older.
    • Cinnamon Bun (described by PB as "basically 30" in "Another Five More Short Graybles") and Flame Princess (14 at the start of her introduction) strike up a friendship in "Earth & Water". He ends up becoming her loyal champion.

  • Amphibia: Combined with Interspecies Friendship. At least 4 characters have formed this with at least one or more person older than they are.
    • Anne Boonchuy is a 13 year old girl, while One-Eyed Wally is either in his 20's, 30's, or 40's. While they got off to a bad start in the first episode with interactions between them being anything but friendly afterwards. They began to warm up to each other after the events of "Toad Tax", and they officially became friends as of "Wally and Anne". Which continued on to episodes such as "Swamp and Sensitivity".
    • Sasha Waybright is a 13 year old girl, while Captain Grime is somewhere in his 50's or 60's. While they got off to a bad start immediately after Sasha arrived in Amphibia, with Grime imprisoning Sasha for about a month, and Sasha manipulating his guards into quitting their jobs, much to Grime's irritation. But they began to see each other as equals after the events of "Prison Break", with Grime even making Sasha his lieutenant. He even gives Anne an angry glare after he saves an injured Sasha from falling to her death in "Reunion". Ever since then, Sasha and Grime became as thick as thieves, and fought by each other's side during their banishment, even after they discovered King Andrias's true colors and formed the resistance along with the citizens of Wartwood. Grime's friendship is what inspired his Heel–Face Turn in the entire show, and sacrificed his left arm to save Sasha from a fatal blow in "All In". When it came time to say their goodbyes, the two go into Ocular Gushers and tell each other that they'll miss each other very much.
    • 13 year old Marcy Wu quickly formed this with the over 1000 year old colossal 30ft tall King Andrias Leviathan. Within their first few minutes of meeting each other, Marcy quickly appeals herself to Andrias by ignoring social protocol, climbs into the pocket of his robe, and then gives him a roblox pin as a friendly gift of friendship. While Andrias tries to downplay their connection, Marcy's energy and kindness towards him was enough for him to go out of his way to convince the Core not to kill her. Even after betraying, stabbing, and letting his master possess Marcy. Andrias still cared about Marcy very much as Andrias expresses guilt whenever interacting with the Core possessed Marcy (aka Darcy) and has a massive My God, What Have I Done? breakdown after listening to a letter from his former frog friend Leif. After this, Andrias finally has a Heel–Face Turn, and let's Anne defeat him to stop him from doing anymore damage. Immediately after his defeat, he begs Anne to save Marcy. Not caring about his own injuries. Later, Andrias finally stands up to his Master by commanding his leftover Frobots in assisting Marcy and her friends by helping them keep the Core from crashing the Moon into Amphibia. In a deleted scene, Marcy smiles back down at him, proud of him for finally doing the right thing. When the time came for Marcy to leave Amphibia for good, Marcy gave a brief but meaningful goodbye to the former king and Andrias tells her to take care of herself. Showing that despite everything that happened between them, the two still care about each other.
    • During the events of "Fixing Frobo" 5 year old Polly Plantar forms a short but meaningful bond with two college students 'Ally and Jess'. While the two girlfriends did not know that Polly is a talking tadpole from another world until "Escape to Amphibia", they were very open-minded to her somewhat strange appearance and went as far as to go to the Boonchuy's home to check on her. Polly even calls them for help when she and her family were building a Christmas float for Anne's parents in "Froggy Little Christmas". Polly even embraces them after they helped save her and her family from Mr X. While they would never see each other again, Ally and Jess's knowledge on robotics helped Polly build a new body for Frobo and later became a mechanic by the 9 month timeskip in Amphibia.
  • Atomic Puppet: Joey is a 12-year-old kid and AP is an adult superhero (who is at least 40 years old based on some lines) turned into a talking sock puppet.
  • Avatar: The Last Airbender features three cases:
    • A strange friendship forms between Toph Beifong (12 years old) and Iroh (64 years old) before they realize they're both on opposite sides; Toph, who has joined the Gaang since they last saw Iroh, encounters him while having a brief falling-out with the others. And when they do realize they're on opposite sides, they don't care.
    • Aang and Bumi (a 12 year old boy and a man well over 100 respectively), though in this case they became friends while they were both kids (Human Popsicle complicates many things, except maybe friendship).
    • One in its sequel The Legend of Korra between Korra, the new Avatar, and Tenzin, the previous Avatar's youngest son. It's also kind of funny when Tenzin develops a Papa Wolf personality towards Korra. Korra is also a Cool Big Sis to his kids.
    • This is implied to happen a lot with Avatars, especially when said Avatars die young (young for an Avatar being the average lifespan of a human) and their friends and family outlive them long enough to meet their reincarnations. Korra has a close relationship with Aang's widow Katara, who served as her waterbending instructor, and quickly befriended his other teachers, Zuko and Toph, after she met them.
    Avatar Roku: Some friendships are so strong, they can even transcend lifetimes.
    • Speaking of Roku, what prompted him to say this was Aang's realization that the elderly Monk Gyatso who befriended him as a child was also friends with Roku when he was young.
    • Korra has a good relationship with Toph's daughters, Lin and Suyin. Lin is in her fifties and two of Suyin's children are older than Korra herself.
    • This also applies to Avatar Kyoshi in The Rise of Kyoshi. Her immediate predecessor died at only 33 so his friends all go looking for his successor. She quickly bonds with his Airbender friend Kelsang, who all-but adopts her as his daughter.
  • Batman Beyond: Terry McGinnis and Bruce Wayne.
  • Beetlejuice features this kind of friendship between Lydia, a 12 year old girl, and the titular character, a several hundred year old Manchild (who was probably in his late 30s at his time of death).
    • To make things Squicky, however, it is implied that Beetlejuice does have a crush on Lydia (including having a part of his mind being an actual shrine to her). And, yes, the pairing is canon.
  • Big City Greens has Cricket Green (a country boy of about 7-9 years old) and Gloria (a barista in her early twenties).
  • Bobby's World: Bobby and his Uncle Ted.
  • The Boondocks is rife with these:
    • Huey and Tom DuBois
    • Riley and Gangstalicious / Thugnificent
    • Riley and Ed Wuncler III / Gin Rummy
    • Tom DuBois and Robert Freeman / Uncle Ruckus
  • Buzz Lightyear of Star Command has an intergenerational friendship between the adult Space Ranger Booster and a little alien girl named Becky, who affectionately refers to Booster as "Pickles".
  • Chicago Party Aunt had Diane and her nephew Daniel, after the latter moved to the former's apartment while taking a gap year from college.
    Daniel: You're not just my aunt, you're also, sadly, my best friend.
    Diane: (to Bonnie) Did you hear that? Best friend!
    Bonnie: He did say "sadly".
  • Chip 'n Dale Rescue Rangers: Monty and Chip, Dale, and Gadget grow into this over the course of "To The Rescue"; although ages are never made explicit, Monty is known to be an old friend of Gadget's father, Geegaw, and the boys don't seem to be much different in age from her. It does help that she seemed to remember him from when she was "knee-high to a knee", though.
  • Chowder: Chowder and Gazpacho.
  • The Cramp Twins: Wayne's (who is around 10 years old) Only Friend is a man named Dirty Joe who is well over his 40's. Despite Wayne being a massive Jerkass toward pretty much everyone in the series, Dirty Joe is the only one he treats with any decency and Joe always enjoys Wayne's company. This is probably due to their similar likes in junk.
  • Danger Mouse, the world's greatest secret agent, and Penfold, his schoolboy-aged assistant.
  • Defenders of the Earth: Mandrake (age unknown but probably in his mid to late thirties or thereabouts) and Kshin (a pre-teen) have this type of relationship. "The Adoption of Kshin", an episode from towards the end of the series, explores how the two of them met and ends with Mandrake formally adopting his young protege.
  • Donkey Kong Country: Besides the canon examples of Donkey and Diddy (a young adult and a preteen boy), Candy and Dixie (a young adult and a preteen girl) are shown to have this kind of friendship, right down to seemingly sharing Candy's house.
  • DuckTales (1987):
    • Roy (the "Duck in the Iron Mask" from the episode of the same name) is many years younger than Scrooge, but the latter shows great respect to his character and talent, and remembers him more fondly than other people from his past adventures.
    • The triplets, Webby, and Doofus Drake are kids and Launchpad is at least in his twenties, but they get along terrifically (although this is somewhat crossed with hero/Hero-Worshipper in Doofus' case).
    • Scrooge is an old man; Launchpad is still quite young. However, the two do see each other as friends in addition to the boss/employee relationship.
  • DuckTales (2017):
    • Dewey Duck, a pre-teen at around 10-11 years of age, is mutually considered best friends with Launchpad McQuack, who is around his late 20s. While this can technically apply for all the kids in relation to Launchpad, none are nearly as close as Dewey is, to the point to where he sometimes can only remember Huey and Louie as "Dewey's brothers."
    • Fenton Crackshell-Cabrera, who is likely in around his early to mid 20s, has become really good friends with Huey Duck, who again is a pre-teen. Unlike Dewey and Launchpad, who get along super well by both being total goofballs, theses two get along well due to their scientific skills being able to help each other out, whether that be with Gizmoduck tech, or helping out with smaller projects. It's shown in "Dangerous Chemistry of Gandra Dee!" that Fenton actually relies on Huey to help him escape from his tiring hero life as Gizmoduck, and Huey was shown to do what he could to make sure Fenton's date with Gandra went well.
    • Downplayed with Louie Duck (as with the other triplets, a pre-teen at around 10-11) and Goldie O'Gilt (150+). In the episode "Happy Birthday, Doofus Drake!" Louie and Goldie team up in order to con out all of Doofus's money for themselves. Of course, Goldie's Chronic Backstabbing Disorder meant that she had every intent to frame Louie when she had the chance, but she ended up risking her life for him while he saved her from the suffering fate as "Goldie Mama." Even after she ran off with all the money, leaving Louie betrayed, Goldie still decided to keep a photo of him in her wallet right next to her dear Scroogey. It seemed Louie grew on her a little more than she expected. This later pays off during the Fountain of Youth adventure, when it was purely Goldie's fondness for Louie that kept her from running off with the Fountain's water and leaving the Duck family to die.
    • While we only see it for one episode, Webby begins a fairly strong friendship with Penumbra after the latter ends up stranded on Earth. While Penny has a hard time adjusting to concepts such as having fun and relaxing, Webby manages to get through to her by discussing how hard it was for her to adjust to life outside the mansion, and how the triplets had to help her grow as a person... and by introducing her to hamburgers. By the end of the episode, Webby has gotten Penny to come out of her shell, and formed a strong friendship with her.
  • Family Guy: Brian Griffin and Stewie Griffin are pretty much this considering Brian is an adult dog and Stewie is a baby.
    • Herbert and Chris also technically count as this trope (even if Herbert wishes it were more than that).
  • Foster's Home for Imaginary Friends has Mac and Frankie, with Mac at 8 and Frankie at 22. Overlaps with a Precocious Crush on Mac's part.
  • Freakazoid! and Sergeant Cosgrove. There was even a Running Gag involving Sergeant Cosgrove pulling up to Freakazoid in his car and asking him if he wants to do something together like bumper cars.
  • Noodle with all her bandmates from the Gorillaz, since she joined them at around age 10, while the other three were already adults. They're all clearly more attached to her than to each other.
  • Gravity Falls:
    • Twelve year old twins Dipper Pines and Mabel Pines are quick to befriend the twenty two year old Soos, a socially awkward Manchild who works at their great uncle's tourist trap. He is also the one who often accompanies them on adventures.
    • Fifteen year old Wendy is also cool with the twins, but the one she really bonds with is Dipper. While this is helped by Dipper having a not-so-subtle crush on the teen, even after giving him the Better as Friends talk, Wendy tells him that she has more fun with him than anyone else she knows.
    • Also technically applies to Gideon and his prison gang, as they are all grown men who follow his orders without hesitation simply because they like him. Even after they were all pardoned.
  • He-Man and the Masters of the Universe (1983) has He-Man and Duncan. Take into account that Duncan is also He-Man's father's advisor/best friend and He-Man's main love interest is Duncan's daughter Teela.
  • Jackie Chan Adventures: Jade and Tohru. Many times, Jade would ride the much larger Tohru on his shoulder. She even gave him half of a yin yang necklace to show their bond. On a similar vein, Paco and El Toro Fuerte.
  • Jem: This occurs in more than a few episodes. Jerrica and her friends are twenty-something year olds. At least two episodes have them befriending seniors.
  • Jonny Quest: Jonny and Race have more of a father/son dynamic; however, in one episode of Real Adventures, Race says that Jonny is his new best friend. Jonny's 13/14 and Race is in his late thirties.
  • Joshua Jones features one of these between the 20-something title character and the 10 year old Ravi.
  • Kim Possible and Shego ("Stop Team Go"), Shego and Drakken (sometimes).
  • In Mighty Mouse: The New Adventures, Mighty Mouse is shown to be close friends with a young orphan named Scrappy.
  • Milo Murphy's Law: Middle-schooler Milo forms a bond with time travelers Cavendish and Dakota, both adults.
    • Cavendish and Dakota themselves possibly fit this trope, since Cavendish sports a grey moustache and acts more grown-up than his (generally) silly partner.
    • In the Season 2 episode "Spy Little Sister", Melissa becomes the "mentee" of Savannah, a female time agent, and they stop a Killer Robot together.
  • Mina and The Count was a series of animated shorts that aired in the Oh Yeah! Cartoons variety show about a five-year-old girl befriending a centuries-old vampire. While popular, Nick decided against making it a full-length series and even stopped making the shorts precisely because they were squeamish about the age gap between the characters.
  • Monster High: Draculaura is 1600 years old, Frankie Stein is (when they met) 16 days old.
  • Motorcity: The Cool Old Guy Jacob is this to the teenage Burners. Texas might also be this to the rest of the Burners, as he appears to be out of his teens.
  • My Little Pony: Friendship Is Magic provides numerous examples:
    • The young filly Apple Bloom and the solitary zebra shaman Zecora bond in "Bridle Gossip" and share both a friendship and an apparent affinity for making potions (although Apple Bloom's, while sometimes successful, tend to have disastrous results).
    • Similarly, there's Scootaloo and Rainbow Dash, with the former idolizing and admiring the latter who fulfills something of a sisterly role.
    • Both Princesses Princess Celestia and Princess Luna act the most "adult" out of any of the characters on the show, being both in their twenties to thirties emotionally and at least a thousand years old each chronologically. They are also good friends with the main cast. Luna also gets this with the young foal Pipsqueak in "Luna Eclipsed".
    • Fluttershy is also good friends with Discord, who is at least a thousand years older than her.
    • In "Grannies Gone Wild", Rainbow is tasked with chaperoning the Golden Horseshoe Gals — Granny Smith, Auntie Applesauce, Apple Rose and Goldie Delicious, all of whom are portrayed as archetypical octogenarians — on their yearly trip to Las Pegasus. At the end of the episode, after a series of misadventures and some friendly bonding, the four older ladies invite Rainbow to be a Golden Horseshoe Gal herself.
  • The Owl House: Luz Noceda is fourteen and Eda Clawthorne is, whilst not quite as elderly as she looks, well over three times that.
    • An interesting case from King and The Collector, as they, at first glance, may be seen as kids around the same age, but while King is around 8 years old, The Collector is more than four hundred years old at the very youngest.
  • The Raccoons: Bert, a young adult, forms friendships with Bentley, a preteen boy, and Lisa, a girl in her late teens.
  • Ready Jet Go!: Jet, Sean, and Sydney, who are possibly in their mid-to-late preteens, are friends with 4-year old Mindy.
  • Recess:
    • Spinelli, who's nine, and Miss Grotke, who's implied to be in her early 30s. Because of this, Spinelli looks up to her like a mother figure (as Spinelli's real mom embaresses her to extreme levels and forces her into girly activities, which she hates). It's adorable.
    • Nine year old T.J. and fifty year old Principal Prickly start off as being each other's Sitcom Arch-Nemesis. As the series goes on they find that they're not that different, and it gets brought to a head in the movie, when he and T.J. work together and T.J. learns more about his past.
  • Rick and Morty has the eponymous duo. They're grandfather and grandson, but act more like (very vitriolic, often toxic) friends, complete with Morty being on a First-Name Basis with Rick instead of calling him "Grandpa". Rick also has this with his granddaughter (and Morty's older sister) Summer.
  • The Simpsons:
  • Sonic the Hedgehog (SatAM): The Freedom Fighters (most of whom are in their teens) have such a relationship with the elderly Sir Charles "Uncle Chuck" Hedgehog. The same could also be said of Tails — who is only ten — and the rest of the Freedom Fighters.
  • South Park: In the episode "A Boy and a Priest", Father Maxi forms one with Butters, who sees the Pedophile Priest jokes the other adults crack whenever they go to church as no different from the bullying he used to go through at school, and approaches Maxi out of sympathy.
  • Steven Universe, besides the Mayfly–December Friendship some of the gems have developed with humans, has several examples:
    • Fourteen-year-old Steven Quartz Universe is friends with the ambiguously college-aged Cool Kids, Lars and Sadie, as well as Jamie, who seems to be somewhere in his twenties.
    • Connie Maheswaran is a bit shy of thirteen and good friends with Greg, who is around 40.
  • Pretty much all Transformer - human friendships are like this, due to the near-immortality of the Transformer race (bar accident or murder). It's slightly mediated in the sense that many of them (such as the Kid-Appeal Character) have childish personalities.
  • The Venture Bros.: While they're both adults in the present day, Henchman 24 was an adult when he first was recruited by the Monarch. Henchman 21 was recruited/kidnapped when he was 15, and the two were basically inseparable until 24's death in Season 3. 21 then became the Monarch's top henchman and close friend, who is about 24's age (or older).
  • The Wacky Adventures of Ronald McDonald: Ronald McDonald and Grimace are most likely adults (with Hamburglar and Birdie's ages in this continuity hard to determine), and they are friends with two children named Tika and Franklin.
  • We Bare Bears: 10-year-old Chloe is the three adult Bears' closest human friend.
  • WordGirl: The title character was once good friends with Steven Boxlitner who was much older than herself. Even though Steven is now the villainous Two Brains, Word Girl still has some sort of friendship with him.

    Real Life 
  • Laura Dern and Shailene Woodley (who is 24 years Dern's junior) became close friends during filming The Fault in Our Stars, to the point that Woodley claimed she lived part time in Dern's house.
  • Dame Margot Fonteyn and Rudolf Nureyev. Best friends, best ballet partners... and she was 19 years older than him. In fact, Dame Margot was about to retire when they started dancing together, but then she decided otherwise and they were a ballet duo for fifteen more years.
  • Lady Gaga and Cyndi Lauper. Despite their age difference of 32 years, they get along very well; Gaga considers Cyndi to be a Cool Big Sis figure, and Cyndi feels as though she can be as weird as she likes when she's with Gaga.
    • Gaga is also friends with Danny Trejo, a 42 year age difference.
    • And with Elton John (39 years), even becoming the godmother of his adoptive kids.
    • And Tony Bennett (60 years!), starting when they recorded a song (specifically, "The Lady Is A Tramp") for Bennett's Duets II CD. It was so well received that they did a whole album together, entitled Cheek To Cheek, released in autumn 2014.
  • While she was in her eighties, Alice Roosevelt Longworth (daughter of Theodore Roosevelt) became friends with forty-something Bobby Kennedy.
  • Michael Jackson and either Dame Elizabeth Taylor (difference of 26 years) or Diana Ross (14 years). Jackson was also good friends with Macaulay Culkin (a 21 year age difference).
  • Emma Roberts and Jennifer Aniston have a 22 year age gap between them.
  • Animal example: A baby hippopotamus that was rescued after floods in Kenya made news everywhere when it befriended a 100-year old tortoise in a wildlife sanctuary.
    • Also, a 47-year-old gorilla and a much younger rabbit.
    • For that matter, Koko the gorilla, and her kitten. Unfortunately, it ended rather tragically.
  • When Christopher McCandless, the subject of book and film Into the Wild, was traveling to Alaska, he briefly stayed with and befriended an old man (given the pseudonym "Ronald Franz" in the book). Franz became deeply attached to McCandless, and prayed for his safety when he left. He became an atheist after Chris's death, believing that any god who would let him die wasn't worth believing in.
  • Sigourney Weaver and Carrie Henn (Newt) became very good friends during and after the filming of Aliens, despite Sigourney being 37 years old and Carrie only a 9-year-old child.
  • Leonard Nimoy and Zachary Quinto, the two Spocks with an age difference of 47 years. In fact, whenever they had the time, they would visit each other in Los Angeles and New York. When Zachary heard of Leonard's death, he was in Berlin doing reshoots for a film, so quickly dropped everything to fly back to the States for the funeral.
  • Despite being 26 years older than him, John McCain was friends with Jon Stewart. Even more impressive considering how different their political beliefs were.
  • Disney star Zendaya and country singer Wynonna Judd, with an age difference of 32 years.
  • Mara Wilson and Danny DeVito, as a result of the two appearing closely together in Matilda.
  • Chuck Norris and Justin Bieber. No, really.
  • Celebrity chef Robert Irvine and his mentor Chef Harold Hillard. The latter is 43 years older than the former.
  • Conventions, anime conventions in particular, can have these spring up. You're a thirteen year old at your very first con and have no idea where to start or what to do first? Not to fear—if you just ask, some friendly college-aged (or older!) veterans who've done this a thousand times will be happy to show you around.
  • Wolfgang Amadeus Mozart and Joseph Haydn were firm friends for decades, in spite of the fact that they were very different people, and that Haydn had several children who were older than Mozart.
  • Indie rocker Kristin Hersh of Throwing Muses was friends was 1940s Hollywood actress Betty Hutton for the last two decades of Hutton's life despite a 45 year age gap.
  • Thanks to Arrow, John Barrowman has struck something like this with most of the cast. Being 47, he's over ten years older than Stephen Amell (the lead of the show), and twice the age of Colton Haynes, Emily Bett Rickards, and Willa Holland, yet, going from videos they've made on set, he seems to be best friends with the kids on set.
  • Jonah Hill is apparently close friends with Dustin Hoffman, who even got him a role in I ♡ Huckabees.
  • From the Today show:
    • Willard Scott and Katie Couric (difference of 23 years). It's most visible during The '90s on both said show and the Macy's Thanksgiving Day Parade — he's old enough to be her dad, but they get along like brother and sister. And it is adorable.
    • The same can be said for him and Al Roker (difference of 20 years), who was Scott's successor on Today. Roker says that he learned everything he knows about being a weatherman from Scott, and considers him as a second father because they get along so well.
  • Kurt Cobain and William S. Burroughs. Cobain loved Naked Lunch and would often keep a copy of the book with him. The two collaborated on a project, The "Priest" They Called Him.
  • Bill Mumy and Jonathan Harris. They remained friends ever since they filmed together on Lost in Space, and Mumy even read Harris' eulogy.
  • Katharine Hepburn and BRIAN BLESSED (29 years difference) became friends during filming Trojan Women.
    • Also, Katharine Hepburn and Lauren Bacall (17 years difference).
  • Groucho Marx and Alice Cooper (47 years difference), after singing a duet together at Frank Sinatra's birthday party. Groucho coined the term "Vaudeville" to describe Alice's style of music.
    • Groucho also befriended Bud Cort (58 years difference), who stayed at the Marx's home for three years and claims he accidentally swallowed a tooth Groucho gave him as a memento.
  • Brie Larson and Jacob Tremblay (16 years difference) became close friends during the filming of Room.
  • Patty Duke and Dove Cameron, starting when the former appeared on the latter's TV show.
  • Peter Capaldi and Jenna Coleman of Doctor Who who, despite a 25-year age gap, struck up an intense friendship that is clearly evident whenever they get together off-screen for interviews and conventions (a prime example being the 2016 AwesomeCon event in Washington, DC). In fact their friendship is so close, and the two are so open about indicating their love and affection for one another - with Coleman directly identifying Capaldi as one of her best friends and Capaldi speaking at length at how unusual it is for two people of their disparate ages to have such a friendship - that a subset of Doctor Who fandom began to ship the actors, despite Capaldi having been happily married for nearly as long as Coleman has been alive.
  • The Channel 4 documentary "Old People's Home for 4 Year Olds" brings children aged 3 or 4 to an retirement village were the producers plan activities in home they will befriend each other. At the start and end of the programme tests are given on their health to see if there is any health benefits for both age groups.
  • Sesame Street puppeteer Carroll Spinney and young fan Nick Bertch, who became friends despite an age gap of at least 60 years. The adorable story can be found here.
  • In his later years, Wyatt Earp developed friendships with actors, William S. Hart and Tom Mix, who both frequently appeared in cowboy movies around that time. When Earp died, they served as pallbearers at his funeral. Tom Mix reportedly wept.
  • Lucille Ball and Carol Burnett developed a friendship when Lucy showed up to one of her stage performances. Later, when Carol had a TV special, she hesitantly called Lucy to be a part of it, and before she could even get it out, Lucy asked, "What do you want me to do?" After that, Lucy would send Carol flowers on her birthday. Lucy ended up dying on Carol's birthday in 1989, and that afternoon when she heard the news, her flowers arrived.
  • At the age of 11, the Dalai Lama befriended Austrian mountaineer Heinrich Harrer, who was 36 at the time. They remained friends until Harrer's death in 2006.
  • Conan O'Brian and his assistant Sona Movsesian, with 17-year age gap.
  • Joan Crawford and Steven Spielberg met while filming the pilot episode of Night Gallery. They became friends despite an age gap of at leastnote  38 years and Crawford's initial reservations about being directed by a twenty-something newcomer.
  • Mother Teresa and Princess Diana (50-year age gap) became friends after the latter paid a visit to one of the former hospices, bonding over a shared sense of humanitarianism. Coincidentally, the two died the same week, and Diana was buried with a rosary that had been given to her by Teresa.
  • Lin-Manuel Miranda and "Weird Al" Yankovic (20-year age gap) are huge fans of each other's work. In 2018 Al recorded "The Hamilton Polka", a polka medley using songs from Miranda's Hamilton, which Miranda was very happy about. Another fun fact: both of them were awarded stars on the Hollywood Walk of Fame for 2018, and they were hanging out together when they got the news.
  • Paul McCartney has a knack for making new friends from his connections in the music industry, and that's continued even as he's grown far older than most of his peers. Decades-younger pals of his include Taylor Swift, Kanye West and Dave Grohl.
  • Matthew Modine formed a close friendship with Millie Bobby Brown, with whom he has forty-five-year age gap with, on the set of Stranger Things. Modine has said that he felt protective of Brown and tried to prepare her for fame at such a young age (Brown was only twelve years old when the first season came out and catapulted her to stardom), having known many a Former Child Star who let the pressures of celebrity get to them, and even lived in Brown's family's guesthouse while filming the first season.


 
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Alternative Title(s): May December Friendship

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Peter Prickly and T.J.

After having helped to save Summer Vacation from Benedicts' machinations, Principal Prickly and T.J. have a little heart-to-heart as Prickly remembers why he decided to get into teaching in the first place: because he cares about kids.

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