Serenade Your Lover

In your eyes, I see the doorway to a thousand churches...

"Once you've got her trust, it's time to make her feel special. Pick a song with her name in it. That always works."

— Catherine Wyler, Not Another Teen Movie

Classic proof of love, from one paramour to another: Singing a love song to them.

Comes in two varieties: The solo serenade, where it's just the two of them alone together, or the public affair, where a crowd of people is watching. The former is more intimate, the latter is more showy, and if it is successful, may result in a Concert Kiss. Serenading someone in front of a crowd is a sign the performer isn't afraid to let everyone know they're in love. It's also a perfect set-up for a spectacular backfire if the suitor is unwelcome and/or utterly without musical talent. Solo serenades are often done under a balcony or outside window, usually with a guitar; Karaoke Bonding Scene might also be used in modern works.

Any romantic song will do, but you get bonus points if the song has the crush's name in it.

Predominantly male, for some reason, but female examples are not unheard of, like the iconic scene from Macross Frontier.

A Sub-Trope of Grand Romantic Gesture.

A Sister Trope to Let's Duet and Old-Fashioned Rowboat Date.

It could also be a Gift of Song.

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Examples:

Anime & Manga

• Played With in The Dangers in My Heart. Kyōtarō Ichikawa himself doesn’t sing the song. His older sister (An actual musician) Kana does. He'd most likely die from stage fright if he did, but the lyrics came directly from him. Long story short, his sister wrote the song from a note he made of his girlfriend Yamada's Love Confession to him, thinking they were lyrics he made. Three days before Kana's band plays it live, Kyōtarō made adjustments and added in a version of his previous Love Confession to Yamada for the 2nd half of the song amongst other things, indirectly declaring just how much he loves her when Yamada attends the show.
• Macross Frontier has a famous scene in episode 15 in which pop idols Ranka Lee and Sheryl Nome both sing a love song to Alto, providing the former page image for Love Triangle.

Comic Books

• Raina sings "Just Like Heaven" to Craig in Blankets.
• Robin: Played With where Stephanie doesn't sing but plays the piano for Tim. While she says she's been meaning to play the piano, and specifically that song, for him for a while when she finally does so it's a somber mood rather than a romantic one as she's trying to come to terms with her father's death.
• Subverted in Strangers in Paradise, when Francine makes Katchoo sing "Love Me Tender" while Katchoo's locked outside their apartment.

Comic Strips

• Krazy Kat loved this trope, and often used a "mandoleen" and a balcony as shorthand for romance in general.
• Subverted and Played for Laughs in this◊ Quino strip. He imagines his loved one's reaction. Being splashed with a bucket of water but then being thrown a rose from her window. He sings for her, and gets the wet treatment and a cold shoulder.
• One Sherman's Lagoon arc has Hawthorn the hermit crab fall in love with a lady crab. At one point, he goes up to what he thinks is her den and tries this trope, but unfortunately sang to a clam. Even more unfortunately, the serenade worked, and he then had a love-struck clam following him.

Fan Works

• In By the Book, Apple tries serenading Daring (with woodland creatures as backup), but Darling runs off with an excuse before she can.
• Dungeon Keeper Ami has Dark General Jadeite thinking about doing this to his new boss, Keeper Mercury, as a way to make her fall more in love with him.
• Kingdom Hearts Ψ: The Seeker of Darkness: In Adjustments, Roxas serenades Xion with "It Is You (I Have Loved)", mentioning that it's from the soundtrack of one of Sora's favourite movies. It's not until some time later that Xion finds out what that movie was.
• In Phineas and Ferb fanworks, Phineas often sings "Gitchee Gitchee Goo" to Isabella as a declaration of love. Once as a lullaby, and another time as a karaoke duet.
• In Someone to Watch Over Me, Adrien plays a piano piece to Ladybug that he wrote specifically about her, leading to her to kiss him while he's trying to explain.
• In A Thing of Vikings, King Magnus serenades Ruffnut while courting her. Ruffnut responds by singing "For The Dancing and The Dreaming".

Films — Animation

• Manolo's primary tactic for winning Maria's heart in The Book of Life. He did so unwittingly with "Creep" and intentionally with "I Love You Too Much".
• Coco: Ernesto does this in one of his movies Miguel is watching in the attic.
• How to Train Your Dragon 2: During their initial courtship, Stoick serenaded Valka with "For The Dancing and The Dreaming". When they reunite in the Bewilderbeast's refuge, he sings it to her again, and she joins in.

Films — Live-Action

• 10 Things I Hate About You has a great example of the public serenade, where Patrick "borrows" school equipment to sing "Can't Take My Eyes Off of You" to Kat... in front of a stadium full of his peers. And then the marching band kicks in...
• The shepherd sings a song to The Baker's Wife from below their window. The baker hears this but mistakes it for a serenade to his bread-baking.
• Parodied in Barbie (2023). As a display of machoness Beach Ken serenades Stereotypical Barbie by playing "Push"...for four hours. And then the camera pans out to show that all the Kens have brought the Barbies to the beach and are playing them the same song.
• The Beatles did their fair share of this in their movies, though always as a group. They even parodied the trope in A Hard Day's Night by singing "If I Fell"...to Ringo.
• In Breaking Away the opera-loving teen protagonist sings an aria for the girl he likes.
• In The Bold Caballero, Don Diego serenades Isabella outside her inn window playing a guitar which magically acquires a full orchestral accompaniment.
• Diary of a Wimpy Kid: Dog Days has Rodrick trying to win Heather Hills with a rock version of "Baby". Hilarity Ensues.
• Guy sings "Night and Day" to Mimi in The Gay Divorcee.
• Double Subversion from Get Over It: a drunk Burke sings "Allison" outside his ex-girlfriend Allison's window, but he does it horribly and she is disgusted. Later in the film, Allison's new boyfriend and Burke's rival, Striker, sings a much better version in front of a crowd of people.
• Three different versions of Orchids In Moonlight is used in Flying Down to Rio. The first is a solo piano piece (no lyrics) from Roger to Belinha as he's making it up (which leads to their first kiss). The second is when he's made it a huge musical number for her. The third time is when Julio, who also loves Belinha, sings her the lyrics and tells her how the song could make any woman fall in love with any man (referencing how she's fallen for Roger), but his version does receive a hug and her begging him to marry her.
• A very young Elijah Wood sings "You Are My Sunshine" to a girl that he has a crush on in Forever Young.
• In Meet the Feebles, Robert the hedgehog serenades his love, Lucille, by playing a song with her name on a mandolin. It is easily one of the least disturbing scenes in the movie.
• Nerve has Ian dared to do this for the Vee, the girl who he just met (because out of such a dare, she just kissed him lovingly!). The diner is already playing some Roy Orbison, so cue him doing a musical performance for her.
• Buster Keaton does this in the Columbia sound short Pest From the West, being a wealthy visitor to Mexico who falls in love with a woman and tries to win her heart. She eventually falls for him after she slaps him when the serenade is done, and he responds by bashing the guitar over her head.
• The Road a Year Long: Katarina has taken up residence in Big Mouth's house—hers having been demolished for the road—but she rebuffs his sexual advances and kicks him out of the house. He demands his guitar, so she hands it to him through a window. He immediately starts singing her a love song.
• The 10 Things I Hate About You scene is parodied in Not Another Teen Movie, where the lead character is told that to win a girl's heart, he should sing a song with her name in it (see page quote). Since she's Janey, he gets in front of the stadium full of his peers and sings "Janie's Got a Gun"; Janey is promptly tackled to the ground and tasered on suspicion of bringing a weapon to school. It doesn't help that he added her last name to the existing lyrics.
• In Nutty Professor II: The Klumps, Sherman tries to propose to his colleague with the help of a Mariachi band who repeat (in song) everything he says. It's very sweet...until Buddy Love takes over and starts making VERY awkward double entendres, like "Why don't you come over here and let me put the beef in your taco?"
• Gerry does this in his second meeting with Holly in P.S. I Love You, singing "Galway Girl".
• In The Palm Beach Story, J.D. Hackensacker does this to Gerry outside her window. Unfortunately, Gerry is with Tom, she asks him to Zip Me Up, and the two get back together again.
• In Ring of Fear, Pedro is serenading his latest romantic interest outside her caravan window with a guitar. She dumps a bucket of water of him.
• Although he doesn't sing per se, this is basically what Lloyd is doing standing outside Diane's window with a boombox in Say Anything....
• In Swing Time, Lucky finally gets Penny to forgive him for messing up their chance for a nightclub audition by singing "The Way You Look Tonight."
• There is the famous "You've Lost That Lovin' Feeling" scene from Top Gun.
• Jerry does this three times in Top Hat: Sandman Dance, Isn't It A Lovely Day and Cheek To Cheek.
• Toninho serenades his estranged wife Isabella after cheating on her in Woman On Top. He doesn't win her back but he does score a job on her cooking show.
• When Adelina goes to jail in Yesterday, Today, and Tomorrow, her husband serenades her from outside the prison fence.

Literature

• The George Selden novel The Cricket in Times Square features a scene where Chester's playing prompts Mama Bellini to remember Papa serenading her in this fashion when they were courting back in Italy.
• Grandmaster of Demonic Cultivation: Mo Dao Zu Shi:
  • In the past, the ill-ridden Wei Wuxian once asked Lan Wangji to sing for him. Being unusually willing to hear out his crush's request, the latter hummed a melody in response. The song left such an impression on Wei Wuxian that 13 years later he plays this very song to calm down Wen Ning after his resurrection — and it's what allows Lan Wangji to recognize who "Mo Xuanyu" really is because he had only played that song once for Wei Wuxian and Wei Wuxian only. It's later revealed that Lan Wangji composed that song just for him, and even named it after the two of them, "Wangxian".
  • In a trivia fact revealed by the author (adapted as an audio drama extra), even after they're married, Jin Zixuan decided to recite to Jiang Yanli a romantic poem that he had made for her years ago. The poem was, while genuinely heartfelt, also cheesy enough that his wife couldn't help but laugh once he was out of earshot.
• Helva, The Ship Who... Sang, got that title in the first place because she and her first brawn loved to sing together, and Helva's unique Beautiful Singing Voice means she can sing in any register. When her brawn dies Helva sings at his funeral and thinks that her singing has died with him, but she returns to music before long and becomes Famed In-Story for singing - particularly when she finds love again, though Niall isn't much for singing back.
  • In The City Who Fought, Simeon tries to win over his prickly new brawn by playing her music, culminating in a recording of Helva's most romantic crooning. Which works, and they call a truce and find a Commonality Connection that leads to the kind of Pseudo-Romantic Friendship that marks many good brain-brawn pairings.
• Mentioned in Soul Music as being one of the main sources of income for a guitar maker: when a serenading troubadour is jumping out the window to escape an angry husband, taking his guitar with him is the last thing on his mind.
• Pufftail in Stray enjoyed courting many female cats using his singing voice. Unfortunately for him, many humans didn't like having cats yowling at night, so they'd often throw water at him.

Live-Action TV

• Ally McBeal: Characters were fond of going to a bar where they could perform. Sometimes couples performed together, or a song was a birthday present from a friend but Serenading One's Lover happened from time to time.
  • John sang a rock song to Kimmy, who he dated briefly. He told an unfortunate half-truth, half-lie that he used to sing at school. He was very anxious, very dorky, and not actually a good singer, but the ladies from his office asked everybody to cheer him up and applaud him, and it helped to create a believable aura of a rocker. Kimmy was thrilled and loved every bit of his performance.
  • Ally's boyfriend Larry sang her "Every Breath You Take" for her birthday. With Sting himself. Even Birthday Hater Ally, depressed even more that year because Larry seemed to forget about it, defrosted and loved it.
• The Big Bang Theory: Howard sings a crazy love song for Bernadette when they are broken up, accompanying himself on the keyboard, in the Cheesecake Factory where she works. People seem a bit embarrassed, but it turns out she loves it and they get back together.
• In the Black Books episode "Fever", Bernard attempts to woo his 'summer girl' Alice with a serenade. On accordion. Alice isn't interested to begin with...
  Bernard: Hello! I've come to serenade you. I can't play guitar. I can't play this either, but I thought it'd be less obvious.
• Buffy the Vampire Slayer. "Under Your Spell", Tara's song to her fellow witch and lesbian lover Willow in the Musical Episode "Once More With Feeling". Subverted when Tara sings a Dark Reprise after discovering she literally is under Willow's spell; having had her memory altered by a forgetting spell. The two break up in the following episode.
• In one episode of La Catrina, Carlos serenades Jamie.
• Woody Boyd serenades his girlfriend Kelly for her birthday in an episode of Cheers.
• Chespirito:
  • In the "Juleo and Rumieta" episode of El Chapulín Colorado, at one point Juleo goes to give Rumieta a serenade, singing the Mexican song "El Rey". Hilarity Ensues when Juleo starts repeating the line "Llorar y llorar" like a Broken Record, apparently because he forgot the rest of the lyrics.
  • In El Chavo del ocho, Professor Jirafales comes to visit the neighborhood one night to give Doña Florinda a serenade, even bringing a mariachi along. Unfortunately, that same night Mr. Barriga is lurking around dressed as a Bedsheet Ghost to scare El Chavo, and Doña Florinda pulls out a shotgun that she fires to the air, scaring the mariachi away. The Professor still decides to sing for her acapella, much to El Chavo's chagrin as he tries to cover his ears.
• Played With in the pilot film of a British series Cold Feet when Rachel essentially invokes this trope. Her long time boyfriend breaks up with her because of a job out of town. She's broken-hearted but very soon meets Adam who is absolutely taken with her and they start dating. He's madly in love with her and asks what he can do to prove his love. Rachel says she wants him to sing her a serenade. While he's naked. With a rose in his butt. They laugh it off. Some time later, however, her ex returns and begs her to take him back, which she does, breaking Adam's heart. Cue Adam, singing a serenade for Rachel under her window, completely naked and with a rose in his butt. Adam wins and she dumps the jerk for good.
• Chuck: a "playing recorded music" variation at the end of "Chuck vs The Honeymooners", when Chuck plays a recording of "Feeling Good" by Nina Simone and he and Sarah start cuddling together.
  "This is going to be your new favorite song."
• In Community, hipster Vaughn plays the guitar and sings a song he wrote for Annie to win her back. Her friends told him she actually loved Troy and her interest in him (Vaughn) was only an Operation: Jealousy. Britta and Jeff think Vaughn is too lame for cute, young, vulnerable Annie. She has been in love with Troy since high school but she really was into Vaughn as well. The song worked and she and Vaughn start dating.
• Doctor Who: The Cold Open for "The Shakespeare Code" sees Lilith being serenaded by her lover playing a song on the lute. When he's done,, she invites him inside, supposedly to consummate their relationship. Once he enters the house, he finds her "mothers" waiting. Turns out all three women are actually aliens, who decide to eat the poor guy.
• The Flash (2014): Barry Allen serenades then-girlfriend now wife Iris West-Allen with an original song about their love at the end of the show’s only musical episode. The song ends with Barry proposing to Iris in a romantic Heartwarming Moment.
• Frasier spends an episode making a series of increasingly ridiculous Grand Romantic Gestures to his new girlfriend even though they've only been dating a few weeks. He eventually decides to sing "Oh Babe, What Would You Say?" to her during a charity ball they attend. This proves to be the last straw for Monica and she finally tells Frasier his efforts are just making her uncomfortable.
• As a music-based show, Glee has this happen a few times.
  • An awesome instance happens when Puck sings "Fat Bottom Girls" to a plus-sized girl he's trying to impress. Even the resulting Epic Fail is awesome.
  • The Valentine's Day Episodes has Kurt's crush Blaine admit he wants to sing a love song to a "special someone" Kurt believes is him. It turns out a) Kurt is not who Blaine wants to sing to, b) Kurt has to help Blaine sing his love song to someone else, and c) the "love song" is a particularly racy Intercourse with You song, and d) the serenading ends up getting Blaine's crush fired from his job. Serenading your lover in Glee is Epic Fail indeed.
  • Blaine, backed by the Warblers, appear at WMHS to sing "Somewhere Only We Know" to Kurt after he moves back to McKinley!
  • The episode "Rumours" has Santana singing "Songbird" to Brittany.
    Santana: I've been going through that Rumors album and I found the best song that really goes one step past "Landslide" in expressing my feelings for you. Private feelings.
    Brittany: What about [Brad]?
    Santana: He's just furniture. Sorry, no offense. (Brad shrugs)
  • In the prom episode, when Artie serenades Brittany with "Isn't She Lovely?" as an apology after calling her stupid and a kind of "promposal." She accepts the apology, but not the invitation.
  Mercedes: I thought this song was about a baby?
• Happy Endings, wannabe cool guy Dave has written at least two songs for his fiancee/then girlfriend Alex. One called Love to the Power of Love, and then this one he plays in Fowl Play Date.
  Dave Al I miss you, you're the only one
  I wish I knew how to make you come
  home to me, home to me
  come, come, come!
• How I Met Your Mother: Played for Laughs and Played for Drama. In a flashback, hippie!Barney sings and plays a song for his then-ex-girlfriend Sharon who broke his heart, leaving him for a wealthy suit. He actually videotaped it, and he was half-singing, half-crying, begging her not to leave him. His friends see the tape and mock him, being used to his usual cool and aloof self. But they feel very bad when they find out how badly Sharon screwed him and that he considers this the most humiliating thing that has ever happened to him.
• James May's Man Lab dedicates a segment to learning the art of the serenade; James teaches researcher Charlie how to play the songs of Thomas Campion (1567-1620), and a way to cheat at playing the guitar. Charlie later woos fellow researcher Cassandra and asks her out to lunch.
• Loki: During Loki's Drunken Song in "Lamentis", there is a slow and gentle verse about a "fair maiden" during which Loki looks at Sylvie, foreshadowing his growing feelings for her.
• Somewhat subverted in Love, Victor: after Victor and Benji bond over the song "Call Me Maybe" earlier in the episode 'Battle of the Bands', Benji later sings the same song at the band contest, saying that his band had just started working on the cover, implying that his moment with Victor inspired the song choice. While it might appear to Victor that he is the one being serenaded in the room full of people, Benji possibly sang the song for his boyfriend, Derek.
• On an episode of Moonlighting, Bert sings "Sexual Healing" to Agnes from outside her window, backed by a small jazz combo.
• Schitt's Creek: Patrick serenades David with an acoustic cover of Tina Turner's "Simply the Best" at Rose Apothecary's open mic night. David fears this will backfire and humiliate both of them, but Patrick turns out to be talented and David, as well as the rest of the audience, are moved by his performance. Later, David needs to apologize to Patrick so, in a Call-Back, he dances and lip-synchs to the original track for Patrick.
• Noora serenades William in Skam, this marks him out as her Love Interest for the season.
• Starsky & Hutch: Hutch sings his one-episode ballerina love interest a full love song, 'I Wish I Was...' in "A Body Worth Guarding" - bonus points for the song actually being one of David Soul's.
• Played for laughs on Three's Company. Jack wants to serenade a girl, but he can't sing very well. Solution: Larry sings while hiding in the bushes and Jack lip-syncs.

Music

• Deconstructed in the video for Poets of the Fall's "Carnival of Rust," where the Carnival's automaton Zoltar the Fortuneteller, when activated, treats his customer to a sudden Obsession Song with such indiscriminately Love Hungry overtones that it frightens her off, and makes it painfully clear he's Loving a Shadow instead of a person.

Tabletop Games

• In Pathfinder the drunken adventurer-turned-(slightly less drunken)God Cayden Cailean sometimes serenades the Goddess of Love Shelyn.

Theater

• The Barber of Seville: Act I - Almaviva hires a band of musicians to serenade Rosina below her balcony ("Ecco Ridente in Cielo"). A bit later, he tries again with Figaro's assistance ("Se il mio Nome") to more success.
• The title song in The Desert Song, sung by the Red Shadow to Margot.
• In Don Giovanni, the title character serenades his former lover's maid ('Deh vieni alla finestra') with a mandolin. Played with, as he is not really in love with her.
  • Parodied in P.D.Q. Bach's The Abduction of Figaro, where Peccadillo serenades Blondie with his ukulele, singing the plaintive refrain, "My dog has fleas."◊
• In the opera Don Pasquale, Ernesto sings a serenade (Com'e gentil) to his beloved Norina at the beginning of the final scene. It's part of a scam to make Don Pasquale think his young wife "Sofronia" (actually Norina) is cheating on him, but the sentiments are genuine.
• Some stagings of The Merchant of Venice have made Lorenzo serenade Jessica during the "elopement" scene. Back when adding stuff to Shakespeare when you edited for direction was considered perfectly fine, one copy of the script had an entirely original song for Lorenzo. Another simply stole a few lines from A Midsummer Night's Dream and had him sing them to her.
• In A Midsummer Night's Dream we learn that Lysander has done this to Hermia offstage, much to the annoyance of her dad.
  Thou has by moonlight at her window sung,
  With faining voice verses of feigning love...
• In Pagliacci's Show Within a Show, the Arlecchin (Tonio) serenades Colombina (Nedda).
• The Unsinkable Molly Brown has Johnny detain Molly outside the Saddle Rock Saloon to sing her "I've A'ready Started In," assisted by a male quartet, one of whom plays the guitar.
• In the The Gondoliers, the song "We're called Gondolieri" has the Gondoliers of Venice sing about their typical day, which apparently consists of serenading their lovers rather than ferrying people about the canals in their gondolas.

Video Games

• In Fire Emblem Fates, out of the Elegant Classical Musician Azura's potential boyfriends, Arthur uses a song to give her a Love Confession.
• In Grand Theft Auto: Vice City, Fernando Martinez references this trope on the "Emotion" station.
  "Have you noticed how popular synthesizers are getting? It's not the same as a lonely man with a pony tail, singing of his love on a guitar, at the door of a fair maid's hacienda. But it is not far short."
• In Love & Pies, Sam sings a love song to Amelia when she calls him over to interrogate him about the sabotage on Esme's van. She's not impressed because he just bragged about how "better" he was than his twin brother Joe in song.
• The Sims:
  • The Sims 2, one of your flirting options is getting down on one knee and serenade the other person (not terribly well, mind you). In The Sims 3 this is an option at a certain level of guitar skill.
  • The Sims Medieval also has this option.
  • The Sims 4 lets you do it with or without a musical instrument, but you need to be very skilled with the instrument in question for the interaction to be available.
• You can tell Miis to do this to confess their love in Tomodachi Life.

Visual Novels

• The protagonist of Melody plays a song for the title character while she’s sick. It helps her drift off to sleep.

Web Animation

• In the RWBY episode "Extracurricular", Jaune Arc tries to convince Weiss Schnee to go to the school dance with him by playing a guitar and singing. It doesn't work and she closes the door in his face. He begs her to open the door again, promising not to sing. When she does, he strums the guitar and sings "I Lied!"
• In the Strong Bad Email "do over", Strong Bad attempts to redo the "sisters" email by serenading the two sisters, on Homestar Runner's advice. It's Homestar who ends up falling for Strong Bad, which is not what he had in mind at all.

Web Original

• Parodied through a Noodle Incident by The Nostalgia Chick. She apparently once got herself laid by singing Whitney Houston.
• Go on YouTube. Find any song that features a girl's name prominently. At least one of the comments is bound to say either "I played/sang this for my girlfriend, her name is X", or "my boyfriend played/sang this for me because my name is X".

Western Animation

• Adventure Time:
  • In "Go With Me", part of Jake's plan to get Princess Bubblegum to go out with Finn has him dress Finn in a "lute suit" and sing for the princess.
  • In "Incendium", Jake performs a song while posing as Finn and trying to win over Flame Princess.
  • In "Love Games", the "Crooning" part of the competition involves the couples riding in rowboats and one member of each couple singing a romantic song to their partner.
• In the first episode of the FOX run of The Critic, Jay tries to persuade Alice not to get back together with her ex-husband, Cyrus, who happens to be an expert at wooing her back with serenades. In the end, Jay attempts to counter-serenade Cyrus on accordion, which Jay admits may have crossed the line from cute to idiotic.
• In The Crumpets episode "Croco-Deal", Pa serenades Ma from below their balcony. It's disrupted when their baby son Li'l One stages a threat with a crocodile so he can get his mother's attention.
• Towards the end of one episode of Family Guy, Brian attempts this with a girl he fell in love with during the filming of a reality show by singing outside of her window. The thing is, she only pretended to love him during the taping of the show, and wants nothing more to do with him (he being obsessed over her and leaving her countless voice messages on her answering machine, to the point where he filled it up and bought her a new answering machine so he could keep leaving her messages). How does this end? With an answering machine thrown right at Brian's head.
• Final Space: In Episode 6, Quinn sees all of Gary's old video messages to her. In one, it shows him, dressed in just a Modesty Towel, trying to sing a ballad he wrote for Quinn. While playing on a small, improvised guitar he made from scrap since HUE wouldn’t let him have an actual guitar.
• Kaeloo: In one episode, Stumpy decides to ask Kaeloo to teach him how to attract girls, since she herself is a girl and probably knows what to do. She tries to teach him by making him dress as a girl and sit on a bench, so he will understand what a girl feels like. She then starts trying to serenade him with a song, pretending to be a boy, but he cuts her short because she's an awful singer and a Dreadful Musician.
• In the Kim Possible episode "Stop Team Go", Miss Go (Shego temporarily turned good) dates Mr. Barkin. After she returns to normal, he tracks her to Drakken's lair and serenades her so badly that she sets the guard dogs on him.
• One of the 30-second cartoons of The Little Rascals had Alfalfa serenading Darla. Alfalfa's off-key singing scared Pete away.
• My Little Pony: Friendship Is Magic:
  • In "Hard to Say Anything", Big Macintosh and his romantic rival Feather Bangs both try serenading Sugar Belle at the same time, Mac with a heartfelt country ballad and Feather Bangs with a catchy boy-band pop song. Their increasingly over-the-top performances just make a mess of Sugar Belle's shop and lead to her getting mad at both of them.
  • In "The Perfect Pear", Pear Butter sings a love song to her sweetheart Bright Mac, titled "You're In My Head Like a Catchy Song". For bonus points, Pear Butter is voiced by Felicia Day.
• Pond Life:
  • An episode had Dolly, the protagonist, standing outside her osteopath's house whilst serenading him (badly) with a recorder. She is eventually chased off by the osteopath's cougar wife/girlfriend.
  • This trope is then repeated in the same episode, with Dolly's therapist serenading her.
• The Simpsons does it... a lot:
  • In one Valentine's Day ep, we see Ned serenade his wife, playing the ukulele wearing a heart-shaped costume:
  If you think I'm cuddly
  And you want my comp'ny
  Come on, wifey, let me know.
  • When Principal Skinner was trying to win back Edna, he had the school glee club sing "Oh Edna K" to the tune of "The Lion Sleeps Tonight".
  • In another episode, Homer gets "Weird Al" Yankovic to serenade Marge with a parody of John Mellencamp's "Jack and Diane".
  • Subverted when Kirk Van Houten serenades his ex-wife with "Can I Borrow a Feeling". She's completely unimpressed and the divorce stands.
• Parodied on South Park: Stan is trying to get Wendy back, and one of Wendy's friends suggests he stand outside her window and play a Peter Gabriel song as a romantic gesture, in a reference to Say Anything.... But Stan, rather than choosing "In Your Eyes", chooses the decidedly unromantic "Shock the Monkey". A bit of Fridge Brilliance in the choice of song there; "Shock the Monkey" is about jealousy, according to Word of God, made even more apparent since it then turns out Wendy has been seeing Token behind his back.
• The SpongeBob SquarePants episode "Single Cell Anniversary" is about Plankton consulting SpongeBob for help when he struggles to come up with an idea on what gift to give his computer wife Karen for their anniversary. They eventually decide on making a song to sing to Karen, and later in the episode Plankton sings her a song called "Oh My Karen".
• Used as a gag in Stōked when Reef wakes up everyone early in the morning by serenading Lo with a love song he wrote for her. This being Reef, it’s absolutely terrible in more ways than one. Lo, however, is thoroughly pleased.
  Lo: You totally rock my world, baby!
  Fin: Oh, brother...
• In the Tex Avery cartoon Little 'Tinker, B.O. Skunk, desperately in search of a lover, follows the suggestion of a book that cupid himself gave him and tries to serenade a female raccoon at her balcony. It almost works until she smells him.
• Tom and Jerry:
  • In the cartoon "Solid Serenade", Tom woos his sweetheart by singing "Is You Is or Is You Ain't My Baby" on the bass. Jerry and the local guard dog are not amused.
  • In "Texas Tom", cowboy Tom plays the guitar and "sings" to a very pretty kitty cat.
• In an episode of The Twisted Tales of Felix the Cat, Felix's magic bag gets stolen. Felix becomes despondent, at one point gazing at a series of photos of himself and the bag in various romantic situations. One of the photos has the bag on a balcony and Felix below, serenading with a guitar.
• Irma from W.I.T.C.H. once stated a boy tried (and failed) to serenade her with a banjo.

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