Top Definition
Jailbait. A hot underage girl.
Cause you were Romeo, I was a scarlet letter,
And my daddy said stay away from Juliet.
- Taylor Swift, Love Story
by x1n December 19, 2010

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A visible symbol of something you have done wrong and regretted, or a stigma of a past mistake you made that follows you.
The Puritans required adulterers to wear a scarlet letter, the letter "A" (with a scarlet red color) on a necklace as a penance for their wrongdoing.
by jakk765 November 14, 2013

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*The stigma of a close family member's mistakes and sins, that seems to follow a person, along with the guilt of what that family member has done to others- And the over-all guilt that comes with having been related to that person.* <-(referring to the use of the term, "wearing a scarlet letter," when the family members of serial killers/ murderers feel so overwhelmed by what their family member has done, they carry the guilt of these crimes on themselves and the stigma of being related to that person. i.e. in the case of the infamous, "happy face killer," the daughter of the serial killer referred to it as, "still wearing a scarlet letter."
In the case of the infamous, "happy face killer." The Daughter of the killer (while being interviewed on t.v) had said something like:
"Yes, I do feel I am still wearing (the) a scarlet letter, because of the horrible things my Father has done to people."
by Akasha A. Wolf January 19, 2016

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a forbidden woman; someone with a shady past who is ostracized from the community.

From the book by Nathaniel Hawthorne, The Scarlet Letter.
"Stay away from Juliet, she's a scarlet letter."
by katerdidit December 02, 2008

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stigma related to the infamous incidents
For example, if you were caught to have a sex deal with a prostitute in China, your passport may be stamped with a seal of "lewd worm". This infamous seal is the "scarlet letter"
He bears the scarlet letter for his frivolous indiscretion in the past
by vanderpol August 01, 2010

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When a male is having sex doggy style with his significant other. She is menstruating (heavy flow) and he pulls out before he is about to ejaculate. He ejaculates on her butt. Then takes the tip of his bloody penis and writes the first letter of his first name on her right butt cheek.
I would like to take you out to a seafood dinner, perform a scarlet letter, and not call u the next day.
by Cheeky Swamps November 16, 2014

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After fucking a girl who's on her period, as you cum, you titty fuck her. Extra props for being able to form the letter A.
My girl was on the rag, but I fucked her anyways, and then I finished it with a Scarlet Letter.
by Hester Prynne November 06, 2006

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