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A term coined by American actor Charlie Sheen on the news show 2020 March 1rst 2011 to describe his unique philosphy on life.
by newguyinthehizzouse March 7, 2011
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An ironic display of triumph over a situation that is, in fact, partly or totally self-destructive or harmful.
Example #1: "My kid got into Harvard and it'll cost me my entire retirement savings to send them there. WINNING!"

Example #2: "I'm a reasonably decent actor with a fat bank account, but I've chased two wives and five children away with out-of-control partying, drug use and violence that's laughable for someone my age. WINNING!"
by PFabian187 March 7, 2011
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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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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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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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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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