Just being to cool for ANY ONE; being better than everyone else. Also is now a famous quote by "Charlie Sheen."
Well lets just say you will never know what winning feel likes.
by Rlvers March 11, 2011
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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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A phrase used by actor Charlie Sheen to describe a plethora of feelings and attitudes. Can be used for both expressing excitement and joy, or used to answer a question.
Example A

(Charlie Sheen receives a suprise)

Charlie Sheen: Winning!

Example B

Reporter: Are you bi-polar?
Charlie Sheen: Psh. I'm bi-winning.
by Shareeb4Prez March 4, 2011
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When a male successfully sleeps with a female of choice.
Female "hey Brandenn...let's get a hotel tonight"
Male "only if i am winning"
by you will never get this February 11, 2010
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Something that awesome people do on a daily basis; If the person has awesome hair, they are considered to be doing this; If the person has multiple people, men or women crushing on them at once...they are partially winning.
Alex is always winning.

Alex's hair looks pretty, therefore he has achieved winning status.

Alex is never losing the game, he is always winning.
by African^____^dancer April 18, 2011
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