History Main / SerenadeYourLover

* PlayedWith in ''Manga/TheDangersInMyHeart''. Kyōtarō Ichikawa himself doesn’t sing the song. His older sister (An actual musician) Kana does. [[ShrinkingViolet He'd most likely die from stage fright if he did]], but the lyrics came directly from him. [[spoiler: Long story short, his sister wrote the song from a note he made of his girlfriend Yamada's LoveConfession 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 LoveConfession to Yamada for the 2nd half of the song, indirectly declaring ''how much'' he loves her when Yamada attends the show.]]

** In ''The City Who Fought'', [[SpaceStation Simeon]] tries to [[MusicSoothesTheSavageBeast 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 CommonalityConnection that leads to the kind of PseudoRomanticFrienship that marks many good brain-brawn pairings.

* In ''Film/RingOfFear'', ComicRelief Pedro is serenading his latest romantic interest outside her caravan window with a guitar. She dumps a bucket of water of him.

* Played With in the ''ComicBook/RobinSeries'' 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.

* ''Fanfic/KingdomHeartsPsiTheSeekerOfDarkness'': In ''[[https://archiveofourown.org/works/16458608/chapters/39115876 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 [[BrickJoke some time]] [[https://archiveofourown.org/works/27158971/chapters/66327586 later]] that Xion finds out [[WesternAnimation/{{Shrek}} what that movie was]].

* In ''WesternAnimation/PhineasAndFerb'' fanworks, Phineas often sings Gitchee Gitchee Goo to Isabella as a declaration of love. Once as [[https://www.deviantart.com/phineas-isabellaclub/art/Phineas-and-Isabella-Fanfic-01-132495099 a lullaby]], and another time [[Fanfic/FindingDad as a karaoke duet]].

* ''Series/AllyMcBeal'': 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.

* ''Series/DoctorWho'': The ColdOpen 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 por guy.
* ''Series/TheFlash2014'': 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 Sugarwiki/{{Heartwarming Moment|s}}.

** ''VideoGame/{{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 ''VideoGame/{{The Sims 3}}'' this is an option at a certain level of guitar skill.

* In ''Film/ThePalmBeachStory'', J.D. Hackensacker does this to Gerry outside her window. Unfortunately, Gerry is with Tom, she asks him to ZipHerUp, and the two get back together again.

-->'''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.\\

* ''Series/{{Loki|2021}}: During Loki's DrunkenSong in "Lamentis", there is a slow and gentle verse about a "fair maiden" during which Loki [[HeldGaze looks at Sylvie]], foreshadowing his growing feelings for her.

* ''Series/JamesMaysManLab'' dedicates a segment to learning the art of the serenade; James teaches researcher Charlie how to play the songs of [[RunningGag 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.z

* Woody Boyd serenades his girlfriend Kelly for her birthday in an episode of ''Series/{{Cheers}}.

* ''Film/{{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 [[SuspiciouslyAproposMusic playing some Roy Orbison,]] [[https://www.youtube.com/watch?v=Ewq82hWitSs so cue him doing]] [[ChewingTheScenery a musical performance for her.]]

* ''Anime/MacrossFrontier'' has a [[https://www.youtube.com/watch?v=TlouKiNPw28 famous scene in episode 15]] in which [[IdolSinger pop idols]] [[BettyAndVeronica Ranka Lee and Sheryl Nome]] ''both'' sing a love song to Alto, providing the page image for LoveTriangle.

* In ''Theatre/AMidsummerNightsDream'' 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...
* Some stagings of ''Theatre/TheMerchantOfVenice'' 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 ''Theatre/AMidsummerNightsDream'' and had him sing them to her.

* In ''Don Giovanni'', the title character serenades his former lover's maid ('Deh vieni alla finestra') with a mandolin. Played with, as he is [[TheCasanova not really in love with her.]]

* In ''Pagliacci'''s ShowWithinAShow, the Arlecchin ([[TenorBoy Tonio]]) serenades Colombina (Nedda).
* 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.

* In ''VideoGame/GrandTheftAutoViceCity'', Fernando Martinez references this trope [[Radio/GTARadio 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 ''VideoGame/FireEmblemFates'', out of the ElegantClassicalMusician Azura's potential boyfriends, [[BornUnlucky Arthur]] uses a song to give her a LoveConfession.

* In the ''WebAnimation/{{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 "''ILied!''"

** 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.

* In the first episode of the FOX run of ''WesternAnimation/TheCritic'', 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 [[TheVillainSucksSong counter-serenade Cyrus]] on accordion, which Jay admits may have crossed the line from cute to idiotic.
* In the [[WesternAnimation/TexAveryMGMCartoons 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.
* ''WesternAnimation/PondLife'':
** 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 [[PsychoLesbian therapist]] serenading ''her''.
* One of the 30-second cartoons of ''WesternAnimation/TheLittleRascals'' had Alfalfa serenading Darla. Alfalfa's off-key singing scared Pete away.
* In the ''WesternAnimation/KimPossible'' episode "Stop Team Go", [[MisplacedKindergartenTeacher Miss Go]] (Shego [[MirrorMoralityMachine temporarily turned good]]) dates Mr. Barkin. After she returns to normal, he tracks her to Drakken's lair and serenades her [[DreadfulMusician so badly]] that she [[AngryGuardDog sets the guard dogs on him]].

* Towards the end of one episode of ''WesternAnimation/FamilyGuy'', 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.
* Used as a gag in ''WesternAnimation/{{Stoked}}'' 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...

* ''WesternAnimation/{{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 [[HollywoodToneDeaf an awful singer]] and a DreadfulMusician.
* The ''WesternAnimation/SpongeBobSquarePants'' 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".
* In ''WesternAnimation/TheCrumpets'' episode "Croco-Deal", Pa [[https://www.youtube.com/watch?v=MGSdP3e5-tI&t=10m10s 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.
* ''WesternAnimation/FinalSpace'': In Episode 6, Quinn sees all of Gary's old video messages to her. In one, it shows him, dressed in just a ModestyTowel, 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.

* Raina sings "Just Like Heaven" to Craig in ''Blankets''.
* Played With in the ''ComicBook/RobinSeries'' 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.

* ''ComicStrip/KrazyKat'' loved this trope, and often used a "mandoleen" and a balcony as shorthand for romance in general.

* In WesternAnimation/PhineasAndFerb fanworks, Phineas often sings Gitchee Gitchee Goo to Isabella as a declaration of love. Once as [[https://www.deviantart.com/phineas-isabellaclub/art/Phineas-and-Isabella-Fanfic-01-132495099 a lullaby]], and another time [[Fanfic/FindingDad as a karaoke duet]].
* In ''Fanfic/SomeoneToWatchOverMe'', Adrien plays a piano piece to Ladybug that he wrote specifically about her, [[spoiler: leading to her to [[ShutUpKiss kiss him while he's trying to explain]]]].

* The above scene is parodied beautifully in ''Film/NotAnotherTeenMovie'', 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 "[[Music/{{Aerosmith}} Janie's Got a Gun]]"; Janey is promptly tackled to the ground and tasered [[AxesAtSchool on suspicion of bringing a weapon to school]]. It doesn't help that he added her last name to the existing lyrics.
* Although he doesn't sing ''per se'', this is basically what Lloyd is doing standing outside Diane's window with a boombox in ''Film/SayAnything''.

* When Adelina goes to jail in ''Film/YesterdayTodayAndTomorrow'', her husband serenades her from outside the prison fence.
* There is the famous "You've Lost That Lovin' Feeling" scene from ''Film/TopGun''.
* In ''Film/MeetTheFeebles'', 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.
* A very young Elijah Wood sings "You Are My Sunshine" to a girl that he has a crush on in ''Forever Young''.

* Guy sings "Night and Day" to Mimi in ''Film/TheGayDivorcee.''
* Jerry does this three times in ''Film/TopHat'': ''Sandman Dance'', ''Isn't It A Lovely Day'' and ''Cheek To Cheek''.
* In ''Film/SwingTime,'' Lucky finally gets Penny to forgive him for messing up their chance for a nightclub audition by singing "The Way You Look Tonight."

* In ''Film/NuttyProfessorIITheKlumps'', 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?"
* Music/TheBeatles did their fair share of this in their movies, though always as a group. They even [[ParodiedTrope parodied the trope]] in ''Film/AHardDaysNight'' by singing "If I Fell"...to ''Ringo''.
* ''Film/DiaryOfAWimpyKidDogDays'' [[https://www.youtube.com/watch?v=-5DXb2qBtwM has Rodrick trying to win Heather Hills with a rock version of]] [[Music/JustinBieber "Baby"]]. HilarityEnsues.
* In ''Film/BreakingAway'' the opera-loving teen protagonist sings an aria for the girl he likes.
* ''Film/{{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 [[SuspiciouslyAproposMusic playing some Roy Orbison,]] [[https://www.youtube.com/watch?v=Ewq82hWitSs so cue him doing]] [[ChewingTheScenery a musical performance for her.]]
* Creator/BusterKeaton 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 shepherd sings a song to ''Film/TheBakersWife'' from below their window. The baker hears this [[ComicallyMissingThePoint but mistakes it for a serenade to his bread-baking]].
* Toninho serenades his estranged wife Isabella after cheating on her in ''Film/WomanOnTop''. He doesn't win her back but he does score a job on her cooking show.
* In ''Film/TheBoldCaballero'', Don Diego serenades Isabella outside her inn window playing a guitar which magically acquires a full orchestral accompaniment.

* ''Series/HappyEndings'', 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 PlayDate.
--> '''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!

--> '''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 [[[ThePianoPlayer Brad]]]?
--> '''Santana:''' He's just [[LivingProp furniture.]] Sorry, no offense. (Brad shrugs)

* In one episode of ''Series/LaCatrina'', Carlos serenades Jamie.
* In the ''Series/BlackBooks'' 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.
* ''Series/JamesMaysManLab'' dedicates a segment to learning the art of the serenade; James teaches researcher Charlie how to play the songs of [[RunningGag 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.
* ''Series/BuffyTheVampireSlayer''. "Under Your Spell", Tara's song to her fellow witch and lesbian lover Willow in the MusicalEpisode "Once More With Feeling". Subverted when Tara sings a DarkReprise 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.
* PlayedWith in the pilot film of a British series ''Series/ColdFeet'' when Rachel essentially [[InvokedTrope 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.
* ''Series/AllyMcBeal'': 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 Music/{{Sting}} himself. Even BirthdayHater Ally, depressed even more that year because Larry seemed to forget about it, defrosted and loved it.
* ''Series/TheBigBangTheory'': 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.
* On an episode of ''Series/{{Moonlighting}}'', Bert sings "Sexual Healing" to Agnes from outside her window, backed by a small jazz combo.
* Played for laughs on ''Series/ThreesCompany''. 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.

* In ''Series/{{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 OperationJealousy. 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.

* ''Series/SchittsCreek'': 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 CallBack, he dances and lip-synchs to the original track for Patrick.
* Woody Boyd serenades his girlfriend Kelly for her birthday in an episode of ''Series/{{Cheers}}.
* Somewhat subverted in ''Series/LoveVictor'': 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.

* One ''ComicStrip/ShermansLagoon'' 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 try this trope, but unfortunately sang to a clam. Even more unfortunately, the serenade worked, and he then had a love-struck clam following him.

* ''Series/JamesMaysManLab'' dedicates a segment to learning the art of the serenade; James teaches researcher Charlie how play the songs of [[RunningGag 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.

* ''WesternAnimation/FinalSpace'': In Episode 6, Quinn sees all of Gary's old video messages to her. In one, it shows him, dressed in just a ModestyTowel, trying to sing a balad 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.

* Parodied on ''WesternAnimation/SouthPark'': Stan is trying to get Wendy back, and one of Wendy's friends suggests he stand outside her window and play a Music/PeterGabriel song as a romantic gesture, in a reference to ''Film/SayAnything''. But Stan, rather than choosing "In Your Eyes", chooses the decidedly unromantic "Shock the Monkey". A bit of FridgeBrilliance in the choice of song there; "Shock the Monkey" is about jealousy, according to WordOfGod.