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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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17
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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18
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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19
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 10, 2010
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20
Verb; See Charlie Sheen. To act as Charlie does. To snort cocaine, to be Charlie Sheen. To have fun. To be successful
Charlie Sheen: "I'm not Bi-Polar...I'm Bi-Winning."

Scoreboard don’t lie, folks. I’ll be over here winning. Done. End of story.”

“Wow, WINNING! It’s all how you perceive it.”

“When I got ready, at a lightning pace – but, like surprise, that’s what winners do.”

“There’s my life. Deal with it. Oh wait, can’t process it. Losers! Winning. Bu-bye.”

“After I’ve won. Keep winning.”
by The Snides March 05, 2011
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