History Main / UptightLovesWild

* ''Film/BringingUpBaby'' -- although in something of a variation, it's Wild who falls for Uptight first, Uptight for many reasons wanting nothing to do with her for a large part of the movie. Wild doesn't so much teach Uptight to loosen up as she does drag him kicking and screaming into it.

* An unremarkable short film called ''Film/{{Headlong}}''. As the reviewer at Website/SomethingAwful puts it:

* ''Series/FlyingBlind,'' a short-lived series from 1992, explored the difficulties faced by self-conscious and repressed Neil in dealing with the erotic antics of liberated Alicia.

* The page quote comes from the ''WesternAnimation/{{Futurama}}'' episode "[[Recap/FuturamaS2E11HowHermesRequisitionedHisGrooveBack How Hermes Requisitioned His Groove Back]]", which features an inversion between substitute bureaucrat Morgan Proctor and Fry. Here is the entire dialogue, immediately after she realizes how badly he maintains his office locker (complete with flies, sticky soda cans, and a ballcap with yogurt in it [[NoodleIncident that Fry claims used to be filled with milk]]):

* ''Film/{{Steam}}'': Elizabeth starts out as a reserved woman with controlling Catholic parents struggling to face her attraction toward woman. She gets into a relationship with Niala, who's proudly bisexual and a rebellious, carefree social activist whom she's instantly attracted to, growing more confident from being with her, though it doesn't last as a result of Niala's cheating on her.

* ''Film/StacyAttackOfTheSchoolgirlZombies'': A teen girl, Eiko, gets a reclusive [[DirtyOldMan middle-aged]] puppeteer, Shibukawa, to promise to "[[FutureSlang repeat kill]]" her when she becomes a [[ZombieApocalypse zombie]]. She's in the [[ComingOfAge final stage]] of becoming a [[OurZombiesAreDifferent zombie]], a stage called, "[[UnusualEuphemism Near Death Happiness]]" [[note]]"Death" used to mean "Orgasm" hundreds of years ago[[/note]] which is a [[AllPeriodsArePMS period]] of [[StepfordSmiler manic giddiness]], as per usual with all girls [[DangerousSixteenthBirthday around the age of 16]], and she'll soon start [[Literature/TheTwilightSaga glowing]] due to the [[NewSpeak B.T.P.]] or "[[WhatKindOfLamePowerIsHeartAnyway Butterfly Twinkle Powder]]." Can [[ManicPixieDreamGirl she help]] him [[AllThatGlitters learn]] to [[PutTheLaughterInSlaughter laugh again]] in this crazy, mixed-up [[CrapSackWorld world]] that's [[EveryoneIsJesusInPurgatory symbolic]] for [[LostAesop lost innocence]]? [[spoiler: Of course, once he [[TheReveal finally]] opens up that [[AnAssKickingChristmas gift]] she [[RelationshipUpgrade gave]] him and finds a [[ChainsawGood chainsaw]] inside!]]

* ''Film/DesertHearts'' is about the lesbian relationship between a repressed, middle-aged English professor and a free-spirited young casino employee-cum-sculptress.

* ''ComicStrip/{{Blondie}}'': Dagwood was the heir to a vast fortune and Blondie was a flighty [[TheFlapper flapper]]... [[spoiler:They have been married since ''1933'']].

* From Franchise/{{Batman}}'s side, his relationship with ComicBook/{{Catwoman}}. He's stoic and disciplined to an inhuman degree, and she's a LovableRogue whose morals are far looser.
* In ''Franchise/TheFlash'', Linda Park is initially very disciplined and is always more focused on her work to a point she doesn't have any friends. And then she meets [[FunPersonified Wally West]]...
* ComicBook/HarleyQuinn and ComicBook/PoisonIvy when they [[RelationshipUpgrade enter a romance with each other]]. The former is an energetic, CuteAndPsycho PsychopathicWomanchild while the latter is a cool-headed FemmeFatale ecoterrorist.

* ''ComicBook/TheSandman'' In "Death: The High Cost Of Living", PerkyGoth called Didi[[note]]who may or may not be [[TheGrimReaper Death]] having a day off: you'll be held in all kinds of suspense unless you happen to have some prior experience with the Sandman Verse, in which case Didi appears very familiar[[/note]] guides a [[EmoTeen teen]] guy named Sexton on a journey of self-discovery and teaches him to respect life and live it to the fullest, and [[AnAesop etcetera]]. A good example of the difference between Wild and ManicPixieDreamGirl, as Didi, while unconventional, spontaneous, and extremely outgoing, is at the same time calm, collected, and thoughtful.

In more recent times, same-sex variations also occur, perhaps unsurprisingly given the reputation homosexuals have for [[AllGaysArePromiscuous wildness]]. The typical formula here will combine the trope with a ComingOutStory, where the protagonist is straight and unhappy until meeting an [[ClosetKey attractive and adventurous]] same-sex love interest -- maybe a glamorous LipstickLesbian for a woman, or a sassy DragQueen for a man, but at any rate, someone who shakes up the status quo.

* ''Franchise/SpiderMan'': Peter Parker and ComicBook/MaryJaneWatson... from both Peter and MJ's perspective: Shy, introverted worrywart (Peter) with one of the most extroverted and charismatic women in the ''Franchise/MarvelUniverse''. From MJ's own point of view, it's also inverted, because she sees herself as a pragmatic levelheaded go-getter girl who was always in control of her life, and then she ended up in a relationship and married to a guy who risks his life on a nightly basis has bizarre experiences and some of the worst luck in the world, and who's often a [[PinballProtagonist pinball for fate]].
* ''Franchise/XMen'': [[ComicBook/{{Cyclops}} Scott Summers]] is an extremely serious and introspective man. ComicBook/JeanGrey is Fire and Life incarnate and acts like it.

* ''Literature/TheDaevabadTrilogy''has straight-laced, highly religious Ali and scrappy con-artist Nahri, who both rub off on each other a little, along with [[TheHedonist hedonistic]] MrViceGuy Muntadhir and his much more honourable [[BodyguardCrush guard captain]] Jamshid.

* The trope image is from ''Film/AlongCamePolly'', in which Creator/BenStiller's character who works in the insurance industry tries a second chance at love with his free-spirited junior high classmate Polly (played by Creator/JenniferAniston).

* Lisa, Wyatt, and Gary from ''Film/WeirdScience''

* ''WesternAnimation/TheOwlHouse'': [[spoiler:The academic and dedicated student Amity ends up dating the rebellious and free-spirited Luz.]]

* ''ComicBook/TheSandman'' In "Death: The High Cost Of Living", PerkyGoth called Didi[[note]]who may or may not be [[TheGrimReaper Death]] having a day off: you'll be held in all kinds of suspense unless you happen to have some prior experience with the Sandman Verse, in which case Didi appears very familiar[[/note]] guides a [[EmoTeen teen]] guy named Sexton on a journey of self-discovery and teaches him to respect life and live it to the fullest, and [[AnAesop etcetera]]. A good example of the difference between Wild and ManicPixieDreamGirl, as Didi, while unconventional, spontaneous, and extremely outgoing, is at the same time calm, collected, and thoughtful.
* ''Franchise/XMen'': [[ComicBook/{{Cyclops}} Scott Summers]] is an extremely serious and introspective man. ComicBook/JeanGrey is Fire and Life incarnate and acts like it.

* In the TabletopGame/{{Pathfinder}} comics, you have spontaneous, hyperactive thief Merisiel and her pious, law-abiding, teetotaler girlfriend Kyra.
* ''ComicBook/TheLegendOfWonderWoman2016'': Etta Candy is a boisterous, rule-breaking, quick-tempered, impulsive college dropout while her love interest Lawrence Stone is an uptight, rule-abiding, slow tempered, and premeditative [[OfficerAndAGentleman USAAF pilot]].

* ''Franchise/SpiderMan'' has Peter Parker and ComicBook/MaryJaneWatson... from both Peter and MJ's perspective:
** Shy, introverted worrywart (Peter) with one of the most extroverted and charismatic women in the ''Franchise/MarvelUniverse''.
** From MJ's own point of view, it's also inverted, because she sees herself as a pragmatic levelheaded go-getter girl who was always in control of her life, and then she ended up in a relationship and married to a guy who risks his life on a nightly basis has bizarre experiences and some of the worst luck in the world, and who's often a [[PinballProtagonist pinball for fate]].
* ''ComicBook/HarleyQuinn'' and ''ComicBook/PoisonIvy'' when they [[RelationshipUpgrade enter a romance with each other]]. The former is an energetic, CuteAndPsycho PsychopathicWomanchild while the latter is a cool-headed FemmeFatale ecoterrorist.

* Two other ''MLP'' fanfics feature the relationship between ElegantClassicalMusician Octavia and uninhibited [=DJ-P0n3=], aka Vinyl Scratch.
** The ''Blog/ReadingRainbowverse'' has Octavia and Vinyl getting married, and everypony is very okay with this.
** In ''Fanfic/TheVinylScratchTapes'', Vinyl and Octavia host a radio talk show together, and their relationship is central to the story.

* Light (uptight) and Ryuk (wild) in ''Fanfic/ACharmedLife''. Ryuk teaches Light that there's more to life than just homework and death whereas Light teaches Ryuk that anything is possible with hard work and determination no matter how ''insane''.
* This happens in the backstory of the ''Franchise/MarvelCinematicUniverse'' fanfic [[https://www.fanfiction.net/s/10255230/1/Canid Canid]] with Coulson and his ex-wife. Unusually for this trope, it didn't work out very well.

* ''Fanfic/ResurrectedMemories'': Danny is normally pretty mellow and he ends up falling in love with the wild, fiery rocker Amberline.
* In ''Fanfic/HellsisterTrilogy'', withdrawn, gloomy Brainiac-5 first falls for outgoing, hot-headed Supergirl and later for Laurel "Clothes are a silly concept" Kent.
* In ''Fanfic/OvercomingTheClashingTides'', Alex Shinji is smart, strategical, and super serious, whereas Cobalt Oak is easy-going and enjoys teasing Alex.
* ''Fanfic/SonOfTheSannin'' has the stoic no-nonsense Shino dating Fu, who is easily excitable and has a rather... [[{{Cloudcuckoolander}} eccentric]] personality.

* Admittedly, it's more a case of Wild Loves Uptight given how much of a {{Tsundere}} [[VideoGame/SuperSmashBros Galeem]] is, but he and Dharkon share this dynamic in ''[[https://incorrectsmashbrosquotes.tumblr.com Incorrect Smash Bros Quotes]]'', with Galeem being a [[NoNonsenseNemesis no-nonsense]], rather neurotic DeadpanSnarker and Dharkon being a cheerful, reckless {{Keet}}.
* ''Fanfic/TheThespianAndThePopStar'': Much like canon, Moxxie is in a relationship like this, only instead of Millie, he instead falls for the wild and sexually promiscuous pop star, Verosika Mayday.
* ''Fanfic/ThePiratesSoldier'': [[Anime/MobileSuitGundamWing Heero Yuy]], a stoic, no-nonsense soldier, quickly finds himself attracted to the LoveableRogue [[Anime/TenchiMuyo Ryoko]], who'd been taken by his looks and personality pretty much on their first meeting.
* ''Webcomic/TheLegendOfGenji'': Fire Lord Shizuka is as strict with her country as she is with her family. Her husband is Riku, a nobleman who loves parties and booze more than politics.

%%* ''Film/TheAfricanQueen''.
%%* ''Film/AngelA''

* Creator/BenStiller is usually typecast as "Mr. Stuffy" whenever he is in a RomanticComedy:
** The trope image is from ''Film/AlongCamePolly'', in which his character who works in the insurance industry tries a second chance at love with his free-spirited junior high classmate Polly (played by Creator/JenniferAniston).
** Deconstructed in ''Film/TheHeartbreakKid2007'', where he impulsively marries an extremely impulsive woman. [[spoiler:It does ''not'' end well]].
** ''[[Film/NightAtTheMuseum Battle of the Smithsonian]]'' has Larry having a platonic romance with UsefulNotes/AmeliaEarhart.
** His character Greg is technically still this in ''Film/MeetTheParents'', but it's harder to notice because his prospective father-in-law Jack is exponentially stuffier than him, which causes loads of awkward and unpleasant situations for Greg, while his Fiancee Pam is far more easygoing and mostly oblivious to Greg's squirming discomfort for much of the film.

* ''Film/StacyAttackOfTheSchoolgirlZombies'': A teen girl, Eiko, gets a reclusive [[DirtyOldMan middle-aged]] puppeteer, Shibukawa, to promise to "[[FutureSlang repeat kill]]" her when she becomes a [[ZombieApocalypse zombie]]. She's in the [[ComingOfAge final stage]] of becoming a [[OurZombiesAreDifferent zombie]], a stage called, "[[UnusualEuphemism Near Death Happiness]]" [[note]]"Death" used to mean "Orgasm" hundreds of years ago[[/note]] which is a [[AllPeriodsArePMS period]] of [[StepfordSmiler manic giddiness]], as per usual with all girls [[DangerousSixteenthBirthday around the age of 16]], and she'll soon start [[Literature/{{Twilight}} glowing]] due to the [[NewSpeak B.T.P.]] or "[[WhatKindOfLamePowerIsHeartAnyway Butterfly Twinkle Powder]]." Can [[ManicPixieDreamGirl she help]] him [[AllThatGlitters learn]] to [[PutTheLaughterInSlaughter laugh again]] in this crazy, mixed-up [[CrapSackWorld world]] that's [[EveryoneIsJesusInPurgatory symbolic]] for [[LostAesop lost innocence]]? [[spoiler: Of course, once he [[TheReveal finally]] opens up that [[AnAssKickingChristmas gift]] she [[RelationshipUpgrade gave]] him and finds a [[ChainsawGood chainsaw]] inside!]]

* ''Who's That Girl'' (1987): A stuffy suit is about to enter into a bad marriage when he meets an ex-con who loves red lipstick and leather jackets... with a pet cougar named Murray. Or, as the trailer puts it, "She's beautiful, she's impulsive, she's... Music/{{Madonna}}! And in 24 hours, she'll turn a mild-mannered, corporate attorney into a wild-eyed fugitive from justice."

* Loretta Chase loves this trope: ''Mr. Impossible'' (Rupert is the wild one, Daphne is the nerd), ''Lord Perfect'' and ''Last Night's Scandal'' (Olivia is the wild one, Peregrine/Lisle is less so). Benedict and Bathsheba from ''Lord Perfect'' seem to be set up to be this trope, except that Bathsheba isn't nearly as wild as her daughter/the rest of her relatives are.
* At the end of the ''Literature/KhaavrenRomances'', it is revealed that [[BloodKnight Tazendra]] has been in love with [[BlueOni Aerich]] all along, and it seems to be mutual.

%% * Remy and Dexter in ''Literature/ThisLullaby'' by Creator/SarahDessen.
* ''Literature/StarTrekNewFrontier'':
** Shelby and Calhoun. He's MilitaryMaverick, and she's by the book.
** Selar and Burgoyne: She's an aloof Vulcan, s/he's from a hedonistic race of hermaphrodites.
* Rebel pilots Braylen Stramm and Gina Moonsong in ''Literature/StarWarsBladeSquadron''. He is a former Imperial military officer who does things by the book, while she is an ex-smuggler who is MildlyMilitary and a FieryRedhead.
* Proper British gentleman Lord Oswald Nelvil, and the titular free-spirited Renaissance woman in Madame de Staël's romance novel, ''Literature/{{Corinne}}''.
* The Light Novel ''Literature/ReaperIvanNavi'' has Life and Death as a married couple and a prime example. Death is much more formal and straight lanced while Life has a tendency to be more wild and generally do whatever he likes despite his wife's occasional objections.
* ''Literature/TheRosieProject'': Don Tillman, who is deeply immersed in his work, lives by a schedule, and has a long test for a potential wife, and the easy-going Rosie ([[spoiler:though she’s an academic as well]]) who is always late, has messy hair and fails every question of Don’s test spectacularly.

* In ''Series/{{Glue}}'', the SecretRelationship between [[spoiler:James and Cal]] is this: the former is [[TheDutifulSon a dutiful son]] and an all-around [[NiceGuy goody-two-shoes]], while the latter is [[spoiler:basically a rentboy and a drug dealer]] and often in trouble with the law.
* ''Series/NeverHaveIEver'': Nalini is an incredibly straitlaced and pragmatic woman. Her beloved husband Mohan was a free spirit who just wanted her to be the Creator/KateHudson to his "Matthew [=McConicky=]."
* Both major couples in ''Series/StarTrekDeepSpaceNine''.
** Worf and Jadzia: he's a stuffy ProudWarriorRaceGuy, she's a Trill with several hundred years' worth of memories who does whatever she can to avoid boredom.
--->"Worf. My love. Let me make this very clear: I do not want to spend ''my'' honeymoon climbing, hiking, sweating, bleeding or suffering in any way."
--->"Alright. What do you want?"
--->"Room service. I wanna be pampered. I want a staff to cater to our every whim - I wanna be ''embarrassed'' by the size of our room."
** Odo and Kira: he's a policeman so uptight he can't stand people moving the things in his room an inch out of place, she's a FieryRedhead ex-guerrilla fighter with little respect for any rules but her own.
* ''Series/QueerAsFolk'': Drew Boyd is a star quarterback who, although engaged to a woman, is a closeted homosexual. Emmett's flamboyant feminine saving force propels Drew out of the closet with a controversial on-air kiss.
* ''Series/TheLWord'': This show verts this trope pretty well, as most people tend to be varying degrees of wild no matter their gender or sexual preference, with the most notable exception being Tasha, uptight and in her rut, being rescued by Alice's feminine saving force, which sends quakes throughout the military and "frees" Tasha from her "oppressors."

* An episode of ''Series/{{Cupid}}'' revolved around this. The title character had to hook the stuffy guy up with an untamed woman, despite their differences.
%%* ''Series/LifeWithDerek'': FlirtyStepSiblings Casey (stuffy) and Derek (untamed).
%% * ''Series/PowerRangersRPM'': In "If Venjix Won", this is Dr. K and Ziggy.

%% * Lisa, Wyatt, and Gary from ''Series/WeirdScience''.
* KissingCousins George Michael and Maeby in ''Series/ArrestedDevelopment''. George Michael was mostly a timid, dutiful son while Maeby was something of an independent delinquent.
* ''Series/AshesToAshes2008'' messes around slightly with [[BelligerentSexualTension Alex and Gene]]; at first it seems that Alex is a BrainyBrunette who is sophisticated, intelligent [[MarriedToTheJob career woman]]) is obviously the uptight one to Gene's fist-happy, racist, sexist, armed bastard of a guy. But then Alex goes and [[AllWomenAreLustful throws herself]] at every guy she meets whilst getting frequently smashed, and it's Gene who [[MyGirlIsNotASlut pulls her up on it.]]
* ''Series/TheBigBangTheory'': Penny moves into an apartment next door to two brilliant but socially awkward physicists and shows them how little they know about life outside of the laboratory. Leonard falls for her immediately and eventually they get together (and then split up, and then get together again, on-and-off it goes). Penny is the untamed one, Leonard the uptight one.
* ''Franchise/{{Buffyverse}}'':
** Angel is moody, broody, and [[GypsyCurse cursed by the Roma]]. Can Buffy help raise his spirits and break the curse? Yes.
** Faith and later Spike try to get Buffy the Uptight Slayer to loosen up. It doesn't end well either.
** StuffyBrit Giles with the lovely Romani granola girl techno-pagan Wicca hippie Ms. Calendar.
%% ** This later happens with Angel's blossoming feelings towards Cordy.
%% * Lee "Apollo" Adama and Kara "Starbuck" Thrace on ''Series/{{Battlestar Galactica|2003}}''.
* ''Series/GossipGirl'' has Blair as an uptight, proper, virginal lady, and Chuck a hedonist who likes his hookers to come in twos. She makes him less wild and more responsible, and he makes her far more sexual and liberated.
* ''Series/ICarly:'' Impulsive, violent juvenile delinquent Sam dates geeky momma's boy Freddie for a while, though she spends a lot of time picking on him up until that point.
* ''Series/{{Skins}}'' with Chris and Jal. Jal inspires Chris to work hard to get and keep a job, and Chris inspires Jal to let her hair down a little.

* ''Series/{{ER}}'':
** Peter Benton and Elizabeth Corday. Deconstructed. Aside from his persistent discomfort over their racial difference (he's black, she's white), his aloof, dour demeanor eventually proves too much of a contrast to her vivacious, fun-loving personality and the relationship fizzles. Though this trope does play very well in regards to their ''friendship'', as even years later, she's one of the few people he's genuinely able to relax around. They even seem to share a quiet moment of understanding in the [[BackForTheFinale series finale]], which aired roughly 11 years after they broke up.
** Kerry Weaver and several of her girlfriends after she comes out of the closet. Her reacting like a scared jackrabbit when encountering her coworkers while on a date, her reluctance to engage in any PDA, etc., quickly irritates and upsets them enough to end the relationship.
%% * ''Series/{{Bewitched}}'': Samantha and Darrin
%% * ''Series/IDreamOfJeannie'': Jeannie and Tony
%% * Sam and Diane in ''Series/{{Cheers}}''.
%% * Fran and Maxwell in ''Series/TheNanny''.
%% * Max and Logan in ''Series/DarkAngel'', especially in the first season.

* ''Series/SesameStreet'': Whether you think of them as HeterosexualLifePartners or AmbiguouslyGay, straight-laced and uptight Bert clearly loves Ernie because of his free-spirited nature.
* Deconstructed with Steve and Miranda on ''Series/SexAndTheCity'', where they have a rather tense on-again, off-again relationship throughout most of the series precisely because their personalities clash too much. Even after they eventually marry, by the time of the movie (4 years after the end of the series), they have an equally strained marriage where every effort he makes to get her to relax is met with irritation.
* In the Hallmark Channel movie ''Christmas In The Air'', a no-nonsense professional organizer is hired by a harried toy inventor to make his personal and professional life more orderly and efficient. Unusually, not only is it the man who is the "wild" one, it's the "uptight" one teaching the "wild" one to get his act together and show him that having a schedule and whatnot is a good thing. Furthermore, he actually ''wants'' her to do this, rather than the resistance typically seen in such scenarios. (Though it still makes the woman the "saving force" as in the trope description. And true to form, the wild one still gets the uptight one to relax and ease up.)

* ''Series/{{Frasier}}'' puts Frasier into this kind of dynamic with one of the [[GirlOfTheWeek Girls Of The Week]] he dates. It's gradually played with to the point of deconstruction as he gradually comes to realise that other than a deep sense of mutual sexual attraction, they really don't have much in common and the relationship likely won't last. Once he gets over his uncertainty about the situation, however, the two eventually agree to just enjoy that whole "mutual sexual attraction" thing for as long as it lasts.
* The main couple in ''Series/MissFishersMurderMysteries'' is this. Phryne Fisher is modern, wild and hasn't met a rule that she isn't interested in breaking. Detective Jack Robinson is stoic, snarky and by-the-book. Over the course of the series, it becomes clear that he settles her down while she loosens him up.

* ''Series/NoTomorrow'': Evie's initial attraction to Xavier, as she's a more shy woman while he's very outgoing and uninhibited. It's {{deconstructed}} however because she doesn't go for {{polyamory}} as he does, but Xavier is willing to commit for Evie.
* ''Series/Reboot2022'': The budding romance between Zack (an immature former child actor) and Elaine (a poised and intelligent studio executive) starts to develop when he gets her to ditch her plans of meetings, outlines, and emails for an afternoon spent running around the studio lot.

%% [[folder:Theater]]
%% * ''Theatre/BarefootInThePark''
%% * ''Theatre/GuysAndDolls''
%% * ''Theatre/{{Rent}}'' - Maureen and Joanne
%% [[/folder]]

* This is how the player character's relationship with [[DefrostingIceQueen Bastila]] appears in ''VideoGame/KnightsOfTheOldRepublic''. Females can also play this card with Carth (who's a bit wound up due to his trust issues), but it takes a gentle approach to win over [[GayOption Juhani]]
* ''Franchise/MassEffect'' has several pairings that end up looking like this, especially Renegade Shepard and Miranda, and to a lesser extent Shepard and Liara.
** There's also ConsummateProfessional Kaidan Alenko stating that he prefers "adventurous women," and potentially falling in love with Shepard, who makes a habit of defying authority and regularly breaks the rules when she needs to get something done.

* Noelle in ''VideoGame/{{Deltarune}}'' is studious, responsible, and nice to a fault. She regrets that she's unable to stand up for herself and do what she actually wants because of that. Hence why she's absolutely smitten with the class delinquent Susie-- she deeply admires Susie's lack of care for following rules.
-->'''Noelle:''' But that's... what's... NICE about you, you know?
-->'''Susie:''' [[BadIsGoodAndGoodIsBad NICE!?]] The hell does that mean???
-->'''Noelle:''' You're the... good kind of scary. You aren't afraid to... break the rules, y'know? ...I wish I could do crazy stuff like you.
* ''VisualNovel/KindredSpiritsOnTheRoof'' has a few couples with this dynamic.
** Most obviously, Aki Ariu, a disciplinary committee member who's stern to the point of being intimidating, falls in love with Youka Koba, a quasi-delinquent rocker who's chronically late.
** The dynamic also is present with Miyu Inamoto and Matsuri Amishima. Miyu is serious, disciplined and tends to plan ahead, while the spontaneous and impulsive Matsuri is practically her polar opposite. While the differences between the two lead to conflict, Miyu admits to herself that Matsuri helps balance her out and allows her to experience new things.

* ''WesternAnimation/{{AdventureTime}}'': Free-spirited, punk rock troublemaker Marceline the Vampire Queen and serious, scientifically genius Princess Bubblegum rekindle their romance as of series finale ''Come Along With Me.''

* ''WesternAnimation/HarleyQuinn2019'': This usual dynamic between Poison Ivy and Harley Quinn is deconstructed and then reconstructed. [[spoiler: The serious, cynical and sarcastic Ivy harbors repressed feelings for Harley, who is crazy, impulsive and uncontrollable. However, Ivy rejects Harley's love precisely because Harley is too unpredictable for Ivy to believe a relationship between them can last or Harley won't hurt her again. Ivy decides it's safer to marry Kite Man because he's steady. Yet Kite Man comes to the realization during their wedding that, despite this, Ivy does truly love Harley more than him and breaks things off with her. Ivy comes to the realization that, regardless of her impulsive personality, Harley still was willing to change for her sake and allows herself to finally reciprocate.]]
* ''WesternAnimation/SheRaAndThePrincessesOfPower'': Hordak is an uptight, grumpy, no-nonsense warlord that doesn't admit failure, especially his. And yet, he falls in love with the free-spirited, hyperactive autistic genius Entrapta, whom teaches him that failure is what makes the greatest discoveries on science possible.

* Courtney and Duncan in ''WesternAnimation/TotalDrama''. She's an uptight priss with high hopes for her future; he's a wild teenage delinquent.
** In ''All Stars,'' Courtney has a fling with Scott, a sneaky farm boy who eats dirt and hunts down rats with a baseball bat.

* Kendall on ''WesternAnimation/KickButtowskiSuburbanDaredevil'' is the residential "Fun Police", a lover of school, rules, books, and opera who seems to be holding a torch for the daredevil Kick... even going so far as to flat out tell her actual boyfriend that she wishes he could be more awesome like him (ouch!). Not that Kick hasn't complimented Kendall on her "elegance"...
* ''WesternAnimation/PhineasAndFerb'''s parents: The [[BritishStuffiness somewhat stuffy]] and decidedly dorky Lawrence [[UglyGuyHotWife is married to]] Linda, whose hit song was titled [[IAmSong "I'm Lindana And]] [[IWantSong I Wanna Have Fun"]].

* The titular character in ''WesternAnimation/MiloMurphysLaw'', a WalkingDisasterArea, has a potentially requited crush on Amanda, a girl who is ObsessivelyOrganized and has a fixation with scheduling her life down to the last detail.
* ''WesternAnimation/{{Kaeloo}}'' has uptight, stuffy Kaeloo and resident bad boy Mr. Cat who couldn't care less about the rules.
* ''WesternAnimation/TheOwlHouse'': [[spoiler:The academic and dedicated student Amity ends up dating the rebellious and free-spirited Luz.]]

-->-- ''WesternAnimation/{{Futurama}}'', "How Hermes Requisitioned His Groove Back"

** StuffyBrit Giles with the lovely Romani granola girl techno-pagan Wicca hippie Ms. Calender.