Love Letter Lunacy

When characters aren't brave enough to come out and say they like someone, the accepted way around a direct confrontation is a love letter, usually anonymously left in a shoe locker or prominent area, with a request to meet at a predetermined location. The intent is better known than the identity of the person; the letter is often pink, in cute handwriting, and smells like perfume. Bonus with lipstick marks.

After the character debates going through with it, they traditionally meet the writer either behind the school or in a field with a big tree.

Sometimes the character does not understand the intent of the letter, but in general the anonymous nature of the letter makes for zany hijinks as characters jump to wild conclusions. This is multiplied if the letter is accidentally left or found by the wrong person.

Popular girls often get these, often from other girls.

To add to the lunacy, just add a ghostwriter who may or may not have feelings for the recipient himself.

Anime and Manga

 * Hilariously sent up in one of the Sailor Moon TV specials and Ami breaks out in hives whenever she sees them.
 * In the first episode of Full Metal Panic!? Fumoffu, Sousuke receives a love letter in his shoebox. His perfectly sensible response is to blow up the school's entry hall because his shoebox has been opened, and interpret the singed 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 Parallel Trouble Adventure Dual, 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.
 * In Neon Genesis Evangelion: At the end of Asuka's first day of school, her shoe locker is entirely filled with love letters.
 * Nagisa in Futari wa Pretty Cure gets unwanted love letters from other girls.
 * Megumi in Tenshi na Konamaiki gets love letters from both sexes, as well as her True Companions and Instant Fanclub.
 * Hazumi in Yami to Boushi to Hon no Tabibito receives love letters from one particular girl whose identity she heartbreakingly fails to figure out.
 * 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.
 * Utena gets dragged into the duels for the Rose Bride as a result of a student council member publicly ridiculing Utena's friend Wakaba for sending him a love letter.
 * She also receives her challenges in the Black Rose arc via letters left in her locker. Though the intent of the note is the opposite, the sender is still a surprise to her when she arrives at the arena.
 * Subversion: In the Love Hina Christmas movie, Keitaro stumbles upon what he thinks is a love letter from Naru to Seta, but, being Keitaro, has mistakenly jumped to a conclusion.
 * Asagiri no Miko bases one episode largely around a misunderstood love letter.
 * Kyon gets two in one episode in Haruhi Suzumiya.
 * Kyon reads out a heartfelt confession and marriage proposal in the 6th novel, . Then it gets thrown out of the window and read by Haruhi. Oh dear Yare yare.
 * A chapter of Yu-Gi-Oh! revolves around one of these made in the form of a jigsaw puzzle.
 * In one episode of Yu-Gi-Oh! GX, Professor Chronos wrote Judai a fake love letter and signed Asuka's name in order to trick Judai into trespassing onto the girls' dorm, thus giving Chronos an excuse to expel him. His plan was messed-up somewhat when Sho found the letter and thought the letter was meant for him.
 * In the Valentine chapter of Fruits Basket Yuki gets a huge amount of chocolates and letters in his shoe locker (apparently this happens every year), except instead of creating a pile each girl would throw the previous one in the bin. The overflowing bin. Hanajima instead decides to steal the current chocolate for the sake of it, much to Yuki's annoyance because he's a gentleman.
 * 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.
 * Tomari from Kashimashi: Girl Meets Girl gets love letters from other girls. This is very much to her dismay, even though she does fall in love with her old childhood buddy Hazumu after he changed into a girl.
 * In Azumanga Daioh, Yukari brings up a love letter whenever Nyamo looks to be about to dish some dirt on her. What exactly happened with this love letter is never clarified, although Fanon generally states that Nyamo wrote it to Yukari at some point as part of a Romantic Two-Girl Friendship, wanting to take it to the next level.
 * There's a deliberate contrast in Powerpuff Girls Z, as Miyako (Bubbles) undergoes daily Love Letter Lunacy (she doesn't mind), while Momoko the Love Lunatic (Blossom) gets none. Karou (Buttercup), meanwhile, is at one point shown with an Instant Fanclub (all girls).
 * In Lucky Star, Kagami appears to get one. Turns out the guy just wanted a trinket that would be embarrasing to ask for in public.
 * In Princess Tutu, Ahiru's friends write a love letter ostensibly from her to Fakir (partly to save her the trouble, partly because they're jerkasses). Luckily, Ahiru gets a chance to explain (and Fakir's reaction is exactly how she predicted it would be from the start).
 * In Hidamari Sketch, Hiro did receive a love letter from an unnamed upperclassman . The one who got nuts was, however, Sae, who freaked out at the prospect of Hiro having a boyfriend, and Yoshinoya, who was sent to the hospital for being a Date Peeper.
 * Noir has Kirika's 'daisuki na Mireille', which spurs Mireille to
 * In Zettai Karen Children, Kaoru tends to get love letters from girls—which she finds troublesome, since she prefers older women. The other two girls get loads more love letters though.
 * 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 Ichigo Mashimaro, 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.
 * 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).
 * A love letter plays a central role in one subplot of Whisper of the Heart.
 * Ritsu, the drummer from the band Hokago Tea Time in K-On!, spends an episode wondering about a mysterious love letter she received. Then her friend Mio (bassist-songwriter) asks her opinion about those song lyrics she left in Ritsu's mail box. Mugi would be disappointed—or 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...
 * 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 D.N.Angel's first chapter, Daisuke gives Risa a love letter, but she turns him down.
 * In Magical Idol Pastel Yumi, Yumi accidentally receives a letter meant for her classmate and ends up helping the sender get a date with the intended recipient.
 * A part of the backstory in Marmalade Boy: Miki wrote Ginta a love letter, and stuck it in a magazine in his bag. This magazine was actually borrowed from another boy, so the owner took it out and read the letter, humiliating Ginta, who vehemently denied any feelings for Miki, claiming she's one of the guys. Miki and Meiko, of course, came back to get something and heard every word... By the time the story begins, Miki is on her road of getting over Ginta, while he Cannot Spit It Out because of the embarrassment over said incident.

Comic Books

 * 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.

Fan Works

 * A particularly complex one appears in the BTS AU fic Cyrano More Like CyraNO: A pair of roommates have a on-demand writing business, and the business partner notices that his writing partner has a Unresolved Sexual Tension-filled crush with a rivalish classmate, so when they are comissioned by an artsy guy to write "secret admirer" letters for his boyfriend, the business partner decides to send the letters the writer makes to his crush without telling him, and ropes his own stepbrother with the actual comission. Chaos ensues as the first writer tries to deflect his work when asked and hide his jealousy over his crush receiving love letters (not knowing that they are the ones he wrote), and the second one begins to interact separately with his comissioner and his target to get a better feeling for his letters and ends falling in love with them both, not noticing that the happy couple aren't actually that bothered and are actually planning to include him into their relationship. Things come to an end when the first writer's crush decides to use the letters he has received in a school project, and debuts it in a reunion where all the above are present...

Film

 * Western example: 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 Mail used the same basic plot, with AOL and the Internet replacing the post office.
 * Both films are based on the play Parfumerie.
 * The whole premise of the 1985 movie Secret Admirer.
 * Amelie 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,.
 * 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.

Literature

 * 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.
 * PG Wodehouse' characters would often write these, but accidentally leave them in the wrong rooms.
 * Sean Bateman receives these in The Rules Of Attraction.
 * 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.
 * Book six of Ranger's Apprentice

Live Action TV

 * 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, a jerky visiting cousin decides to screw with DJ 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.
 * In the 1997 Colombian miniseries Cartas de Amor, love letters are the main method used by matchmaking expert Cupido López, and his letters are pretty effective, granted that he manages to meet both his client and their intended (or actually preferred) target before writing them. The lunacy in this case is that his current assignment is in a small neighborhood plagued with a cynical Casanova bent on interfering with any romantic relationship that doesn't involves him, and that Cupido is actually female and is trying to hide both her actual gender and her increasing love feelings towards the above-mentioned Casanova.

Newspaper Comics

 * 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.

Theater
"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."
 * 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.
 * Later the King, Dumaine and Longaville are all seen writing love letters, overheard one by the next with Reveal after Reveal. Berowne calls them all out on it, until his own love letter is revealed.
 * 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 prideful 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. At Act II, Cyrano, a man with a ridiculous long nose, loves beautiful and eloquent Roxane, but is utterly afraid of her reject. 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 Christian teach him to be eloquent, and lends him the love letter he wrote to Roxane to Christian so he can send it to her in his own name. At 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, risking his life, 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 Shallow Love Interest into a full fleshed heroine decided to save Christian from peril in Act IV.

Video Games

 * 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, I might add...
 * In Persona 4, the protagonist will receive love letters in his shoebox if he does good at tests, usually containing some useful item or other that a secret admirer has made for you. . As the Fortune Social Link reveals, Naoto is also plagued by these on a regular basis ('plagued' because the detective prince has better things to do than play around with romance).
 * 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.
 * In the third Ace Attorney game, series Butt Monkey (literally) 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 schoolgirl 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 and cries rivers of tears.
 * In No More Heroes, Kimmy Howell gives the main character a letter that starts out like this... before taking a turn for the Ax Crazy.
 * Used pretty tragically in Rule of Rose, where Meg's love letter for Diana is not well received, and the protagonist Jennifer gets to suffer ire from both sides after being unwillingly dragged into the mess.
 * Not long before it was shut down, City of Heroes had a Valentine's Day holiday event which included finding lost love letters and then delivering them to their intended recipients—who were often some of the most powerful people in Paragon City or the Rogue Isles. One side benefit—you got to read the letters (in order to find out who they were for, of course), and they were frequently hilarious either for the couples involved, the messages sent, or both.
 * In Undertale, to befriend Alphys you have to give her a love letter from Undyne, since the latter, for all her bravado, doesn't have enough courage to deliver it. Unfortunately, Undyne forgot to sign the letter, so when Alphys receives the letter the believes that the player character is the author, and immediately drags them into a date. Things become sillier from there.

Visual Novels

 * 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.

Web Comics

 * The short story envelop(e), inspired of A True Love Story, had this as its premise. It's mainly notable for having been drawn by Fred Gallagher of Megatokyo fame.
 * 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 believe that Aggie is a lesbian with a secret crush on Penny.
 * Ivan the Apprentice receives a series of decreasingly sane ones
 * In one of the early arcs of CRFH, 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, Fuschia sends Crimney a letter that spits out a heart-shaped flame, followed by heart-shaped puffs of smoke. She means well. . ..

Western Animation

 * In an episode of The Simpsons, Lisa sends a love note to the school bully Nelson, via Milhouse. Thinking that it was Milhouse who is the author of said note, 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 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, who's apparently been getting them throughout the season; later, 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.