Has an origin from a main character of short story with the same name written and published by Washington Irving in 1819. The term is used to describe persons who fall asleep or are absent for sometime, and do not realize what the hell has happened around them when they wake up or return.
Jane: Oh, there you are, Rick. Good luck on the test tomorrow!
Rick: What? There's a test tomorrow?
Jane: Of course! Our teacher told us. Don't you remember?
Rick: No, not really. I was...
Jane: Felling asleep in the class again, right? Seriously, what's wrong with you? Are you Rip Van Winkle?
by manat31790 March 5, 2011
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When a girl wakes up with a penis in her mouth, and notices that the pubes have grown substantially whilst being there.
"Josh thought that it would be funny to injure Brien's balls, so in order to get payback, Brien Rip Van Winkle'd him last night. "

Davis: "I shaved my pubes this morning."
Bennett: "Didn't you shave those a few days ago?"
Davis: "I did, but I Rip Van Winkle'd my bitch again last night, and they grew several inches."

Alex: "What's wrong dude?"
Davis: "I just walked in on my roommate and his girlfriend: she was asleep, his dick was in her mouth, and his pubes were growing at an unnatural rate. Have you ever heard of such a thing?"
Alex: "Foshizzle. The ole' Rip Van Winkle...
by NolaDuncan November 9, 2009
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While camping, when a friend falls asleep and you cum on their eyes so in the morning their eyes are dried shut. Hence the idea of being asleep for 100 years in the woods.
While we were camping last weekend, I gave jon a rip van winkle
by chadmuska25 March 27, 2009
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this is rhyming slang for tinkle} A.K.A. to give someone a call.

Sometimes shortened to "Rip Van "
"Alright mate, i'll give you a Rip Van Winkle later on tonight."
by Bud Mizzleroy September 19, 2005
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To awake and find a female's extremely hairy vagina over your face.
"I just got Rip Van Winkled last night, and I still have hair in my teeth!"
by Thumper168 December 2, 2009
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To intend to take a short nap, but end up sleeping for a much longer period. Refers to the story of Rip Van Winkle who fell asleep for a hundred years.
I meant to take a quick nap before my next class but I ended up ripping a van winkle and missing my midterm.
by TheBleedingPen March 2, 2009
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When more than 3 people purposely trap their genitals in a vehicle door.
"both of us ended up with our bollocks and todgers trapped, it was a proper Rip Van Winkle Festival!"
by hackneydale October 1, 2015
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