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Anime and Manga
- In the first episode of Full Metal Panic? Fumoffu, Sousuke receives a love letter in his shoebox. His perfectly sensible (From the perspective of a former Child Soldier who grew up in an area where IEDs are a common problem) response is to blow up the school's entry hall because his shoebox has been opened, and interpret the signed fragments of letter he retrieves from the ruins as a death threat. To make matters worse (or more humorous), the Student Council President agrees with Sousuke that his actions were the most correct ones. Kaname's reaction look is hilarious.
- In the final "bonus" episode of Dual! Parallel Trouble Adventure, Kazuki becomes the victim of a mostly-benign kidnapping when he responds to what, from his reactions, is the first love letter he's ever received.
- Early in the show, when Kazuki is easing into the new world, alternate versions of the people who tried beat the crap out of him in the first episode for talking to Mitsuki use him as a medium to deliver their love letters.
- Shows up almost as often as cooking duels in Ranma ½
- Very early in the series, Kuno sends what appears to be a challenge letters to Ranma's girl form. It turned out to be a love letter, much to Ranma's distress. Kuno goes on to do this several times over the course of seven seasons.
- Ryoga pulls this at least twice in both the anime and the manga. One story has Ryoga send Akane a love letter written in green ink (it's complicated). The letter gets wet and the ink bleeds so Akane never actually gets to read it. In another, Ryoga's dog Shirokiro actually manages to deliver a love letter to Akane and return with her reply, which says she's already in love with somebody else. Ryoga is devastated until Ranma points out that "somebody else" could just as well be him, since both letters were anonymous- the adaption of this story is actually Ryoga's final appearance in the anime, up until the OAV series.
- In Ukyo's first story after being introduced to the cast, she tries to set up a blind date between Ryoga and Akane using a love letter written on an Okonomiyaki, which Akane naturally mistakes for a challenge from Ukyo. Of course, this isn't helped by the fact that Happosai took a bite out of it (manga)/Ranma stepped on it while chasing Happosai (anime) before Akane could read it, thus blotting out some key kanji.
- Asagiri no Miko bases one episode largely around a misunderstood love letter.
- Kyon gets two in one episode in Haruhi Suzumiya. The first is anonymous, and it turns that Ryoko used it to lure him somewhere private so she could kill him without any witnesses. The second leads to a confusing encounter with Mikuru from the future.
- In the first episode of School Rumble, Tenma Tsukamoto spends all night writing a long love letter to Oji Karasuma. He spends all day and night reading it, and finally ignores it when he realizes the letter wasn't signed. Later in that same episode, Kenji Harima writes a (considerably shorter) love poem to Tenma, and she adores it. Naturally, someone else she just happens to meet in the park after school (who is big enough to pound Harima into paste without a second thought) finds out about the poem and takes the credit for writing it. Later Harima beats the guy to a pulp.
- A few episodes later, Tenma is watching a period drama, and gets the wonderful idea to shoot a love letter at Karasuma with a bow and arrow. She follows him across town as he nonchalantly dodges every attack, unintentionally makes Harima parody The Matrix, and follows Karasuma into a bank just in time to FOIL A BANK ROBBERY.
- In Toradora!, Taiga attempts to leave a love letter for Yuusaku in his bag—but accidentally puts it in Ryuuji's instead. When he finds it later and attempts to look inside, he discovers it's a sealed, empty envelope. She's so klutzy she forgot to put the letter in.
- Kana gets one from Fujioka in the first episode of Minami-ke, but then makes a horrible mistake: she asks her sisters for advice. Chiaki, apparently sincerely, manages to interpret the letter as a challenge. Kana is convinced, and meets with Fujioka in order to kick him. (This is just the beginning of Fujioka's trials; at one point, Chiaki even finds an aggressive way to interpret his out-and-out saying "I like you" to Kana.)
- In Strawberry Marshmallow, Nobue receives a love letter asking to meet her in front of the Hamamatsu Station. The girls try to change her dress and rehearse the meeting... it doesn't go well. It was Miu all along (explaining the feminine handwriting), having gotten the idea from a manga she was reading. Miu crafts another letter from "Junya" saying that he's flying to India... but makes the mistake of signing her own name to the envelope.
- Ana gets her love letter too, after the first day of school. With the plus of being written in Gratuitous English because the writer didn't know she could read Japanese (when in fact the opposite was true).
- Ritsu, the drummer from the K-On! Band, spends an episode wondering about some mysterious love letters she receives. Then her friend Mio (bassist-songwriter) asks her opinion about those song lyrics she left in Ritsu's mail box. Mugi would be disappointed—nor not.
- Nyan Koi! plays with this one interestingly. First Junpei receives a letter, which he thinks might be a love letter, from Nagi, but it turns out to be a challenge letter.
- Then he receives a second (handed to him) by Kotone, which he thinks is about another challenge, but is surprised to find is an actual love letter, only to get it ripped out of his hands only moments after he's read it by who he thinks is Kotone, but is actually her twin sister Akari who challenges him to meet her at a shrine by his house. He finds that Kotone actually does like him (to the point of being a complete stalker) and Akari is trying to keep from being requited. The challenge was more about his curse though.
- Akuma de Sourou begins with shy Kayano trying to give her crush a letter but handing it to another guy instead, prompting a lot of harassment.
- One of the Digimon Adventure Drama Cd's revolves around the Digidestined discovering Izzy typing up a love letter on his laptop. They try to force him to tell them who it is, and when he doesn't, he tries to escape, leading them to tie him up and gag him. They spend the rest of the CD discussing who they think it could possibly be while the poor boy squirms. At one point they actually come to a conclusion that it has to be Mimi, to which he protests as loudly as he could whilst being gagged. He eventually tells them who it is...Too bad the name is edited out. They can hear it, we can't.
- CLANNAD: Sunohara writes an anonymous love letter to Kyou, telling her to meet in a certain place after school. Upon arriving, she finds a message left on the chalkboard, saying that her admirer is actually waiting someplace else. After four or five iterations of being sent to a new location, Sunohara's prank ends when Kyou catches him in the act of writing the next message.
- In episode 4 of Kin-iro Mosaic, Youko receives what appears to be a love letter in her shoe locker. Turns out Shinobu wrote a letter to Alice's parents, hoping Alice would translate it into English. However, it seems like it was Aya who has a problem with that for the whole time.
- Kaitou Saint Tail is rather 'unusual' in this: the love letters are sent by the titular Phantom Thief to the Sympathetic Inspector Antagonist chasing her, they're (barely) masked as the 'burglary warnings' he dared her to send him, they're delivered with stage magic in ways ranging from a doll with a note popping out of nowhere on his head (Saint Tail was improvising and was flustered) to a zeppelin (she was showing off) and a message written on his bath towel as he was getting a shower, and, in spite of the very romantic tone, he didn't realize they were love letters until The Dragon of the final villain called him an idiot and stated the one he had just received while imprisoned and that stated she was about to steal him was an obvious love letter.
- In Lucky Star, Kagami finds a love letter in her locker, and worries about it. Seeing that, Konata can't bring herself to admit it was an April Fools' Day joke.
- In a later manga episode, Kou finds a love letter in her desk, again addressed to Kagami. It passes through Hiyori's hands to Tsukasa, who delivers it to Kagami (not without some teasing from their older sisters). Later, Konata calls and admits that she left a fake love letter in Kagami's desk at graduation, but Kagami went home without noticing it.
- As if Kagami didn't have enough fake love letter issues in the manga, the anime has her receiving a note while on their Class Trip, leaving her distracted the rest of the day. It is actually from a boy this time, and he does actually want to talk to her... about begging the Yatsuhashi doll she bought off of her.
- In episode 3 of Kamen no Maid Guy, Naeka recieves a love letter at her school and spends the episode wondering if she should meet with the sender. At the end she decides to go and even warms up to the idea that she could have a boyfriend, until she discovers that her admirer is actually a female classmate named Saki and when she tries to leave the scene her crazy male butler traps them both in room together so that she "move forward" with her dilemma. It's not hard to tell what happened next.
- In the Anime of the Game for Mega Man Star Force, Cancer Bubble tries to infuriate Luna by "accidentally" delivering spurious love letters from Mega Man to Harp Note. He does this because he's mistaken her for a Barrier Maiden whose powers are awakened by wrath, but he only succeeds in getting her angry at him.
- Early in Yu-Gi-Oh! GX, Dr. Crowler leaves a fake love letter from Alexis in Jaden's locker as part of a plan to lure him into a trap. Unfortunately, Jaden is currently sharing a locker with Syrus who ends up getting the letter and sending Crowler's plan completely Off the Rails.
- In WJHC On The Air, Sandy writes a love letter to Janie but doesn't put either of their names on it. It gets passed around the entire main cast, and Hilarity Ensues.
- Blue Monday: Victor decides to send a mushy letter to Clover asking her to the Valentine's Day dance, but he sticks it in the wrong locker and it ends up in the hands of the incredibly homely Sally instead. Clover then takes the opportunity to mock the letter with her friends.
- In the Disney short film Paperman, the hero realizes the cute girl he met earlier is just on the opposite side of the street from his workplace. He tries to get her attention with a paper airplane, then two, then three... and ends up creating over a hundred out of his work papers trying to get them to reach her. By the time he decides to just screw it and run over there in the middle of his work hours, she's already gone. But all his paper airplanes turn out not to be in vain, as they seemingly come to life and direct them both to each other.
- The 1940 movie The Shop Around the Corner is about two people who are conducting a romance by sending anonymous love letters to each other... and who also happen to hate each other in real life. In 1998, the movie You've Got M@il used the same basic plot, with AOL and the Internet replacing the post office. Both films are based on the play Parfumerie.
- Amélie features a very dragged out version of this that starts out with a note to pick up a lost scrapbook and ends in a romance.
- In The Science of Sleep Stéphane puts a note under Stéphanie's door while he's asleep sleepwalking. Except a) he believed it was actually a dream, b) she saw him do it and c) it was asking for her roommate's phone number even though he isn't interested in her. The next morning he goes to get it back, realising his mistake, except she's already read it.
- In the 1942 musical You Were Never Lovelier, Eduardo Acuña wants his daughter, Maria (Rita Hayworth) to get married, but she's very picky with her suitors. Eventually, he invents a mystery admirer for her, and starts sending flowers to her, accompanied by anonymous love letters, with the intent of presenting his choice for her husband as the writer of the letters. His plan goes awry, when she sees the guy delivering the flowers and thinks that he's the writer.
- In Atonement, the lead male is frustrated trying to write a letter to the lead female, and writes a vulgar, sexually charged one to work out this frustration. Afterwards, he writes a perfectly lovely one and gives it to his love's young sister to deliver. Guess what? Remarkably, rather than wacky hi-jinks ensuing, the vulgar letter works. Well, hi-jinks ensue. They're just not hilarious. More like downright depressing.
- Little Women. Jo and Laurie are, respectively, horrified and amused by the growing UST between Meg and Mr. Brooke, so they play a few pranks on Meg involving love letters and rumors.
- "They" being just Laurie, considering the fact that Jo just wants it all to go away and swears most solemnly to her mother that she had no idea of Laurie's hijinks.
- P. G. Wodehouse' characters would often write these, but accidentally leave them in the wrong rooms.
- Sean Bateman receives these in The Rules of Attraction. he doesn't even know the girl who's sending them to him is alive, and she eventually commits suicide. Nobody cares.
- In Jane Flory's Faraway Dream, Charlotte Sutcliffe receives what she believes is a request from a friend to become his business partner. In fact, it was a marriage proposal. Justified, in that English is Mr. Curcier's second language. They marry.
- In The Red and the Black, the cynical, self-centred protagonist obtains a collection of prewritten love letters from an acquaintance. From then on, he doesn't even bother reading his mistress's letters when they arrive, instead simply copying out another letter, inserting her name in the right places, and sending it to her without another thought.
- In All Men of Genius, Volio tries to blackmail Miriam, who's playing a Matron Chaperone role for the younger Cecily, into carrying love letters between himself and Cecily. Miriam responds by working with her friends to create fake letters from Cecily, fabricating Cecily's side of a drawn-out "correspondence". Volio is pleased at the Purple Prose he's fed (which the real Cecily would consider horrible). They make sure that "Cecily" tells Volio not to approach her directly for the sake of secrecy, but he eventually does so anyway. The real Cecily's simple explanation that someone's been playing a joke on him, making his whole romance with her imaginary, causes him to snap and trigger the book's finale.
Live Action TV
- Our Miss Brooks: The plot of the episode "Bones, Son of Cyrano". A love letter gets misdirected and misinterpreted multiple times. Hilarity Ensues. Especially, when Mr. Conklin believes Miss Brooks is in love with him!
- In the season one finale of Caroline in the City, Richards writes a love letter to Caroline telling her to meet him at Remo's if she accepted. She coincidentally ends up there at the expected time without having read the letter causing Richard to humiliate himself and flee to Paris. Annie finds the unread letter in season two which leads to comical blackmail mayhem.
- The British 1970's-era TV Series Are You Being Served?. In the first-season episode "Dear Sexy Knickers", a saucy note is delivered to the wrong person, who misunderstands who it's from. And when the sender is identified, the recipient is misunderstood. In the meantime, innocent people are cussed out and much Hilarity Ensues.
- In the teen show California Dreams, resident slime ball jerk with a heart of gold Sly wrote these for Lorena.
- In an episode of Full House, Rusty, the jerky son of Danny's girlfriend at the time decides to screw with DJ (who Rusty had a crush on) by writing a love letter to her and having Michelle deliver it. Since the note has no names on it, it gets passed around several times, until nearly everybody thinks it's about them.
- In an early season episode of Smallville Chloe writes a love letter to Clark and reads it to him while he's unconscious and in the hospital. Several seasons later (after Chloe is married to Jimmy Olsen) Clark finds the letter while helping Chloe clean up.
- An episode of Mama's Family revolved around this trope. Vint wants to do something to make Naomi happy, so he has Bubba help him write her a love letter. The letter gets misplaced a few times, and soon Naomi thinks Bubba has an incestuous crush on her, Iola thinks Vint wants to leave Naomi for her, and Mama thinks her refrigerator repairman is coming on to her.
- In Wizards of Waverly Place this happens with one from Alex to Justin.
- In The Adventures of Pete & Pete, the episode "Pete and Pete S2 E12 "Yellow Fever"'" has Ellen receiving an anonymous love letter, much to Pete's annoyance. In season 3 episode "Crisis In The Love Zone", a sweeping epidemic of amore has Ellen writing a love letter to Big Pete, only for Little Pete to wind up with it and thinking it's from his crush.
- In one FoxTrot story line, Peter plays a practical joke where he leaves anonymous notes for Paige, pretending to be a secret admirer. He eventually arranges a meeting where Paige spends several hours sitting in the rain waiting for her secret admirer who never shows. Somehow Paige fails to see the funny side of this.
- Another storyline had Jason, wanting to butter his mom up so he could get a new computer, writes a mushy card meant for her. Unfortunately the notes ends up in Eileen Jacobson's hand. Hilarity Ensues.
- A variation occurs in Much Ado About Nothing. When it is revealed that Benedick and Beatrice only said they loved each other because they each thought the other loved them, love letters they wrote earlier are produced as "evidence" that they truly are in love.
- In Love's Labour's Lost Berowne sends a love letter to Rosaline via country bumpkin Costard; meanwhile Don Armado sends one to Jaqenetta, also through Costard. Naturally the wrong letters get into the wrong hands.
- In Twelfth Night, several characters decide to bring Malvolio down a peg and write a fake love letter to him from their mistress. Because he is a proud fool, he immediately falls for it and believes Olivia is infatuated with him. When he follows the ridiculous instructions left for him in the note, Olivia thinks he's gone mad and has him locked up as a lunatic.
- Cyrano de Bergerac: This trope is a plot point in the play. In Act II, Cyrano, a man with a ridiculous long nose, loves beautiful and eloquent Roxane, but is utterly afraid of her rejection. So he writes a love letter to her, hoping to give it to her and run. When Cyrano discovers Roxane is interested in fair but ineloquent Christian, he realizes that Roxane will be disillusioned with Christian and he cannot let that happen. So he proposes to teach Christian to be eloquent, and lends Christian the love letter he wrote to Roxane to so Christian can send it to her in his own name. In Act III, Cyrano realizes that the eloquence Roxane admires so highly is shallow and decides to speak of his real feelings in the letters he keeps sending her in Christian’s name from the Battlefield twice a day. The whole point is that these new love letters are so powerful in expressing Cyrano’s love to Roxane, that Roxane evolves from a self–admitted Satellite Love Interest into a full fleshed heroine, deciding to save Christian from peril in Act IV.
Cyrano (striking his breast): Ay—a single word of all those here! here! But writing, 'tis easier done…(He takes up the pen): Go to, I will write it, that love-letter! Oh! I have writ it and rewrit it in my own mind so oft that it lies there ready for pen and ink; and if I lay but my soul by my letter-sheet, 'tis naught to do but to copy from it.
- In Final Fantasy IX, Eiko got help from the Doctor Tot to write a love letter to Zidane, and when hung on a peg she's forced to ask Baku to deliver it to Zidane. Baku accidentally drops it and forgets to mention the whole thing to Zidane. This leads to Beatrix believing the letter is from Steiner and vice versa; the two do wind up becoming a couple, and no one's the wiser. Even if Eiko, Blank, Markus and Baku do witness their first tentative meeting. The music that plays during that scene is even entitled, "Foolproof Love Letter Scheme." A nice alternate title for the trope...
- Final Fantasy Type-0's secret ending features Sice trying to work up the courage to give one of these to Kurasame. She apparently believes that a good way to deliver it is to wait around the corner after she sees him walking towards her and wait until the footsteps sound close, then turn around blindly and hold it out with a loud and nervous "Here!" without checking to see if the one standing there is Kurasame and not her fellow classmate Seven.
- Shows up, of all places, in La-Mulana. The dating-sim homage game Lemeza can play on his MSX features one of these that drives the plot. It's anonymous, and asks the nameless protagonist to come to the "legendary tree." It's all perfectly cliche from there on out. Until it turns into a Snatcher homage.
- Ace Attorney:
- In the third game, series Butt Monkey Larry Butz leaves a love letter for his latest crush. However, being the doofus he is, he manages to write it so it looks like blackmail.
- Larry fails at the same task in Ace Attorney Investigations, when his sloppy handwriting causes the name of the recipient to be misread as "Wendy" instead of "Mindy."
- In Capcom's self-parodying game Chibi-Fighters, one of Chun Li's combo enders is her turning into a school girl and shyly handing her opponent a love letter. If she hits, the target reads the letter and then rockets across the screen with hearts in their eyes. If she misses, she gets stunned as she cries rivers of tears.
- There's a quest at the beginning of Fable II called "The Love Letter". In it a poor man asks the Hero to deliver a love letter with a proposal to his girlfriend without her bitter mother finding out. The good option has the Hero deliver the letter to the girlfriend without a hitch. In the evil option however, the hero gives the letter to the mother who gets angry. When confronted by her the man lies and tells her the letter is for her to get out of trouble. She then quickly becomes enraptured with him and accepts his wedding proposal, much to the man's horror.
- Fable I also has a quest involving delivery of a love letter. The evil option in that one is to tell the recipient that you wrote it yourself.
- On the path to Undertale's Golden Ending, Undyne asks you to deliver a love letter to Dr. Alphys, since whenever she tries delivering it herself she backs out because she thinks the letter needs to be rewritten. Unfortunately, she forgot to sign it, and Alphys assumes the letter was from you — so she takes you on a date to the garbage dump, despite obviously only having eyes for Undyne. Undyne, having decided her love letter needs to be rewritten, is looking for you in an attempt to get it back. Hilarity Ensues as you try to get the two of them together.
- In Miku's route of A Profile, Masayuki gets a love letter that his friends immediately assume is a prank until he gets mad at them for instantly assuming bad will. Their position is helped along by the fact the sender forgot to include her name. The sender, for that matter, is annoyed with those friends later because she heard them laughing about it.
- In Rin's route in Little Busters!, Riki receives a very generic love letter in his shoe locker one day. When he waits after school, very confused and curious about who could have left it, the last person to leave is Suginami, a shy girl he's never really talked to. But when he confronts her she clearly didn't know anything about it, and it's revealed that her friends left it on her behalf. Riki is a little relieved...and then she explains that she does like him, and that her friends apparently did it to force her to say something. Riki is flattered and polite but not really interested, and it's this event that leads to Rin asking him out later that day.
- Ultra Fast Pony: In the episode "How Not To Train Your Dragon", Celestia sends a letter to Twilight to finally say exactly how she feels. The letter winds up in the possession of a dragon named Chet instead. And when Twilight overhears Chet reading the letter aloud, she manages to miss the point entirely.
Chet: [reading the letter] Dear Twilight... Can't hold it in any longer... Blah blah blah blah blah. [puts the letter away] Aw, it's just a boring love letter.
Twilight: That doesn't make any sense. Why would Celestia send me a glove letter? I don't wear gloves.
- In Penny and Aggie, Aggie tries to get Duane a date with Penny by leaving a note and concert tickets in her locker. Unfortunately, Penny walks up to the wrong guy at the concert (the note only gave a vague description to identify the secret admirer, which coincidentally applied to two boys) and doesn't see Duane at all. Plus Penny's friend Sarah spots Aggie planting the note, leading her to believe that Aggie is a lesbian with a secret crush on Penny.
- In one of the early arcs of College Roomies from Hell!!!, the guys have Roger send a note to the girls next door asking them out. Roger forgets to bring a pen, so he writes the note using blood from a paper cut. The cut clots before he finishes the message. As a result, the girls end up with a note with "We're coming to get you" written on it in blood slipped under their door. Violence ensues.
- A high-school-era Namir Deiter Valentine's strip had Cedric, whom Tipper was dating at the time, competing with Gabby (her crush on Tipper not yet known to the audience) to see who could leave the more impressive note, bouquet, and chocolates in Tipper's locker.
- In Cardboard Angel, when Mayuko's friends find out she has a crush on Satoru, they insist she write him a love letter as it is "the way it's done." Mayuko is coerced into putting over the top things in it and is forced to try to hand it off to him. Unfortunately, Aya intercepts the letter and uses it to publicly humiliate Mayuko.
- In Sinfest, Fuchsia sends Criminy a letter that spits out a heart-shaped flame, followed by heart-shaped puffs of smoke. She means well...
- In an episode of The Simpsons, Lisa sends a love note to the school bully Nelson, via Milhouse. Thinking that Milhouse is the author, Nelson pummels the crap out of him.
- In an episode of American Dragon: Jake Long, Spud writes a letter to his crush Stacy. Trixie finds it and thinks it's to her from her crush Kyle. She goes to the location determined and enters a dark storage locker where Spud is waiting. You can see where this is going.
- An episode of The Fairly Oddparents had Timmy write a love letter e-mail to Trixie, but lacks the courage to send it. So his parents do it for him. Since magic can't interfere with love (including love letters) he has to enter Cyberspace to get it back.
- An episode of Jimmy Two-Shoes had Jimmy writing a love letter for Cerbee to Jez's dog, the plan was to give it to Jez to read to Jasmine. However, when Beezy gives it to his father, he says "This is from Jez," and it's only after they part that he wonders "Or was it for Jez?"
- In the "X-Treme Torture" episode of Total Drama Island, Bridgette and Gwen find a love poem and spend the rest of the episode trying to figure out both its writer and recipient. They eventually discover it's meant for Leshawna, who's apparently been getting them throughout the season; later, Harold admits to having written them all.
- In the Looney Tunes Mouse-Warming, a teenage mouse falls for a girl mouse who's moved in across the hallway with her parents. Claude Cat notes the situation, and leaves him fake love notes (along with fake threat notes to her parents) in hopes of a quick meal. The mouse soon gets wise to it, and fakes a note to Claude to visit and make friends with the vicious dog in the yard.
- In an episode of Arthur, Francine and the Brain create a fake love letter and give it to Muffy to get back at her for insulting their science fair projects.
- In the CatDog episode "Shriek Loves Dog", Cat writes a love letter to Shriek, so that she and Dog will fall for each other, hoping that the Greaser Dogs will thereby leave him alone. It works until Dog marries Shriek, which causes the Greaser Dogs to move into their house and generally making Cat's life a living hell. Luckily for him, it turns out to be All Just a Dream.
- In Kung Fu Panda: Legends of Awesomeness, Po tries to break Monkey's interest in Ming by forging an angry letter in her name and giving it to Monkey. Monkey mistakes it as Ming inviting him to a date. Needless to say it does not end well.