A lifestyle pioneered by Charlie Sheen and practiced by those in Sheen's Korner. This exclusive society demands Adonis DNA and tiger-worthy behavior of its members. You are either winning, or you're with the trolls.
Roger Ebert: I could get a million followers like Charlie Sheen did, but my wife would leave me and I'd be a poor lonely sap like he is.

Charlie Sheen: Yeah, you really don't know lonely till you've gone to town on 5 chicks at once. Still winning, plan better.
by fingerboom March 10, 2011
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a way to say epic without people wanting to shoot you.

on the internetz the exclamation mark is needed when stated by it's self; when used in a sentence the exclamation mark is optional

when the word is used irl it should not be said by it's self.
unless your friends are hip and know you're not saying "when!"
"dude i got two toys in my kids meal!"
"fuckin win dude!"

facebook:
gr3g- ii got 2 toiyz in mi kidz meal nigga!
RalF- win!
by GregS. December 4, 2010
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Addressing an accomplishment of some sort. E.g when your average friend scores with a hot chick that's a win
I picked up hundred bucks today that's a
Win

I just scored a piece of paper in that dustbin a 5 metres away that's a win
by MOTM November 2, 2015
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The one thing that Darwin, Dawkins, and Hawking have in common.
Man 1: I'm full of religious fail. How do I become a winner?

Man 2: By reading Origin of Species, God Delusion, and A Brief History of Time.
by 2hamsters1couple April 13, 2009
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convincing a girl on webcam to show her vagina
Dude, i was watching bootyshaker69 last night and i got epic win
by douchebag1918 August 25, 2008
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Woman lays belly down so her head is near the edge of the bed. The male places his penis in the woman's mouth, so that the deeper he gos, the harder he can press on the ladies back. The purpose being that they both get what they want. She gets a back rub, he gets head. The deeper he gos, the better\harder he presses on the back.
Her: baby, can I get a backrub?

Him: I've got a Win-Win for ya, dear.
by Piratevalandi March 10, 2018
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What Charlie Sheen does
"The only thing I’m addicted to right now is winning.” -Charlie Sheen
by Viva La Stool March 2, 2011
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