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 17, 2011

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Being on the drug known as Charlie Sheen
I was bangin' 7 gram rocks, that's how I roll - WINNING!
by DragonSpawn March 11, 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 07, 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 03, 2011

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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 01, 2011

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Charlie Sheen
"Duh! Winning!" -Charlie Sheen
by NotWinning March 01, 2011

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Another term for wanking made by bajancanadian
All I do is win win win no matter what cos my name is mat
When I walk up in the building everybody's dacks go up
Winning is when you wank
by Winner987654321 March 24, 2012

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