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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. 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. Solo serenades are often done under a balcony or outside window, usually with a guitar.
- 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. It even used to provide the image for Love Triangle.
- Hilariously subverted in this Quino strip.
- Also subverted in Strangers in Paradise, when Francine makes Katchoo sing "Love Me Tender" while Katchoo's locked outside their apartment.
- Raina sings "Just Like Heaven" to Craig in Blankets.
- Ten Things I Hate About You has a great example of the public serenade, where Patrick "loans" 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 above scene is parodied beautifully 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). He gets in front of the stadium full of his peers and sings "Janey's Got a Gun;" Janey is promptly tackled to the ground and tasered on suspicion of bringing a weapon to school.
- 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.
- 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.
- The Steve Martin remake of Sgt. Bilko, has the army glee club sing "Only You" to his love interest.
- There is, of course, the famous "You've Lost That Lovin' Feeling" scene from Top Gun.
- 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.
- A very young Elijah Wood sings "You Are My Sunshine" to a girl that he has a crush on in Forever Young.
- Jerry does this three times in Top Hat: Sandman Dance, Isn't It A Lovely Day and Cheek To Cheek.
- Gerry does this in his second meeting with Holly in P.S. I Love You, singing Galway Girl.
- In One Hundred Years of Solitude, Pietro Crespi did this to show his love for Amaranta Buendía. Everyone came out to hear him sing - except for her. Pietro went the Spurned Into Suicide way the next morning, and after Amaranta's mother Úrsula called the Hell out of her, she willingly burned one of her hands to prove how much his death pained her.
- 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.
- That same episode (appropriately, 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.
- Not always. It goes over a whole lot better when 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.
- And again 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?
- In one episode of La Catrina, Carlos serenades Jamie.
- 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.
- James Mays Man Lab dedicates a segment to learning the art of the serenade; James teaches researcher Charlie how 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.
- 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.
- On an episode of Family Matters, Eddie tells Steve to do this to Laura in the middle of the night, but it's to get back at her for a prank she played on him. Steve chooses "Feelings" by Morris Alberts, which he sings loudly while playing his accordion. It pisses off not just Laura, but all the neighbors to the point where Steve's parents send him down south to spend a week with his relatives.
- Krazy Kat loved this trope, and often used a "mandoleen" and a balcony as shorthand for romance in general.
Theatre and Opera
- 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.
- 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,
- 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 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.
- 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."
- Parodied through a Noodle Incident by The Nostalgia Chick. She apparently once got herself laid by singing Whitney Houston.
- The Simpsons did it... a lot:
- In one Valentine's Day ep we see Ned serenade his wife, playing the ukelele wearing a heart shaped costume
- 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". It didn't work.
- In another episode, Homer gets "Weird Al" Yankovic to serenade Marge with a parody of John Melloncamp'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 suggest he stand outside her window and play a Peter Gabriel song as a romantic gesture. He chooses "Shock the Monkey".
- In the Tom and Jerry cartoon "Solid Seranade", 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 the first episode of the FOX run of The Critic, Jay tries to convince 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 him on accordion, which he admits may have crossed the line from cute to idiotic. It works, though.
- 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.
- An episode of Pond Life 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.
- One of the 30-second cartoons of The Little Rascals had Alfalfa serenading Darla. Alfalfa's off-key singing scared Pete away.
- 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.
- 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.
- 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".
- Harana is an old Flipino courtship tradition where a guy (manliligaw) who fancies a girl (dalaga) would stand outside her window and sing love songs to her (usually with his friends providing back-up vocals or playing instruments) until she came out and tell him whether she'd date him or not.