Love Letters 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.
- In By the Book, 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.
- In No More Heroes, Kimmy Howell gives the main character a letter that starts out pretty standard... before taking a turn for the Ax-Crazy.
- All of the boss monsters in 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 Nancy Drew: The White Wolf of Icicle Creek, Elsa received several from her boyfriend before he started vandalising her car.
- Ivan the Apprentice of Oglaf receives a series of decreasingly sane ones from his boss' minions as a joke.
- One of the many of the items that SCP Foundation has is a mailbox designated as SCP-1269, which sends romantic letters to its female owners, which quickly become possessive in tone, and later downright crazy and murderous.
- SCP-962 sends these, with humanity being the target of its affection.
- Parodied in the Hardly Working 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, and Sarah herself.
- In the creepypasta, Your Secret Admirer, the story is told in this format.
- There are gacha machines in Japan that dispense these. They're intended for use as pranks.