{{Love Letter}}s generally range from sweet to awkward. But occasionally, they're downright creepy. This usually occurs when a character gets love letters from an obsessive admirer. Typically, there's one creepy letter to start with, but as the recipient doesn't respond, it's followed by dozens more, all written individually and personalized.

The creepiness of the letters can vary, from mild versions where the writer knows ''way'' too much about the recipient to extreme versions where the letters are filled with threats alongside the endearments to anything in between. The one constant is that the letter will always creep the recipient out.

Subtrope to LoveLetter. See also StalkerWithACrush and LoveLetterLunacy.
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!!Examples:

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[[folder:Manga & Anime]]
* In ''Manga/OnePiece'', the pirate Vander Decken has been using his [[ImprobableAimingSkills Mark-Mark Fruit powers]] to send proposal letters to Princess Shirahoshi that follow her wherever she goes. Over time, these messages have evolved into giant axes, to the point where Shirahoshi has to hide in her tower to avoid being killed.
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[[folder:Fan Works]]
* In ''Fanfic/ByTheBook'', Darling Charming gets over a thousand copies of the same love letter from Apple White. Darling ''does'' like Apple back and finds it more annoying than creepy.
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[[folder:Live-Action TV]]
* In ''Series/{{Smallville}}'', the second season episode "Nocturne," a teen whose parents keep him locked in his basement (to control his SuperpoweredEvilSide) escapes occasionally to leave Lana unsigned love poems at her parents' graves.
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[[folder:Music]]
* The Music/BloodHoundGang's "The Ballad Of Chasey Lain" is about a fan of the adult film actress who writes a series of letters to her asking her to perform various sexual acts with him.
* Music/{{Eminem}}'s "Stan" might also count although it's not a love letter but just letters of an obsessive fan to his idol.
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[[folder:Video Games]]
* ''VideoGame/NoMoreHeroes2DesperateStruggle'': [[{{Yandere}} Kimmy Howell]] gives the main character a letter that starts out pretty standard... before taking a turn for the AxCrazy.
* All of the boss monsters in {{VideoGame/Gingiva}} will propose marriage to you, and when you refuse, you are forced to kill them. Each monster has a unique one of these that automatically appears in your inventory afterwards.
* In ''VideoGame/NancyDrew: The White Wolf of Icicle Creek'', Elsa received several from her boyfriend before he started vandalising her car.
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[[folder:Web Animation]]
* ''WebAnimation/AttackOnMika'': In this chapter, [[https://www.youtube.com/watch?v=E9zoEtQiWdk Iketa speaks with Saki]] about someone sending him several love letters to his locker. When Saki gets shoved down the stairs by her sister Gozumi, it's revealed the latter was the one stalking Iketa.
* ''WebAnimation/EtraChanSawIt'': [[https://www.youtube.com/watch?v=iuAQS0NceZs Akane]] had love letters sent to her by an unknown stalker, over which she even lost the will to bully Tsutsuji. Things escalate when the stalker sends photos of her cheating on her fiancee to the office, the man himself, and his parents, driving her to quit her job. In the end, the stalker turns out to be [[spoiler:Yuzuriha, who did this to avenge a childhood friend of hers who took her own life over Akane's bullying in high school and because her coworker Tsutsuji's situation reminded her of said friend's.]]
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[[folder:Webcomics]]
* Ivan the Apprentice of ''Webcomic/{{Oglaf}}'' receives a series of decreasingly sane ones [[spoiler:from his boss' minions as a joke]].
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[[folder:Web Original]]
* One of the many of the items that ''Website/SCPFoundation'' has is a mailbox designated as [[http://scp-wiki.wikidot.com/scp-1269 SCP-1269]], which sends romantic letters to its female owners, which quickly become possessive in tone, and later downright crazy and murderous.
** [[http://www.scp-wiki.net/scp-962 SCP-962]] sends these, with ''humanity'' being the target of its affection.
* Parodied in the ''WebVideo/HardlyWorking'' sketch "My Bloody Valentine". Sarah receives a bunch of increasingly disturbing love notes from Pat which contain stuff like "Bee mine?... THAT WASN'T A QUESTION." Then he kills everyone who flirted with her, [[IfICantHaveYou and Sarah herself]].
* In the creepypasta, “Your Secret Admirer, the story is told in this format.
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[[folder:Other]]
* There are [[http://en.rocketnews24.com/2017/05/06/only-in-japan-handwritten-love-letters-from-high-school-girls-now-available-in-crank-machines/ gacha machines in Japan that dispense these.]] They're intended for use as pranks.
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