(n) A phrase used to describe the coolness of something; (adj) good, cool, the best
"Your shoes are win."
"You got the tickets? Win and win!"
by racerfatty July 14, 2009
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A solution to a conflict which not only benefits both parties involved, but also benefits the mediator for having successfully mediated a conflict. Deemed the most optimal result of a conflict and coined by Michael Scott in the Conflict Resolution episode (twenty-one of season two) of The Office.
Making the poster into a T-shirt and forcing Oscar to wear it was quite a win-win-win solution.
by Free6000Bush June 30, 2011
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A term a smarmy salesman or manager uses to tell you that both parties have positive outcomes from a situation. This is rarely true. see Enterprise bargaining
So you see here we have a win win deal.

Oh yes of course, you take my old car for nothing, and i pay off this new one for the next 38 years, i am a winner then arent i?
by jamesbrown May 2, 2003
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A win-win situation is where all outcomes are desirable.
If you kill him, you'll get respect and the cops won't touch you.

If you don't kill him, someone else will whack that asshole..
by Gumba Gumba February 25, 2004
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Something everyone loves and wants to have/achieve.
Person: He is such a Win-win
by emilie_thesv February 2, 2021
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When a female performs fellatio on a male while he consumes a nice juicy steak.
On March 14th I better get a win win.
by Council of Men February 3, 2012
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As discussed in "The 40 Year-Old Virgin," a win-win is the act of popping any kind of drowsiness inducing drug (Nyquill for example) and proceeding to jerk off. Whether or not one finishes before falling asleep is besides the point because "either way you win..."
Rob: "You going out tonight man?"
Gene: "Nah I'm staying in tonight. I'm pretty tired."

Rob: "You going for a win-win?"

Gene: "Great idea!"
by Wolf man February 28, 2012
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