Apparently Charlie Sheen is doing a lot of it and tweeting about it constantly.
Banged another two hookers and snorted 5 lines of coke. I really am #winning.
by celebrator1975 March 9, 2011
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
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
(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
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
Something everyone loves and wants to have/achieve.
Person: He is such a Win-win
by emilie_thesv February 2, 2021
Full of win. Anything withholding the properties of success.
Tyler's doomsday2.jpg picture was rather winful.
by Andy Winsamosdebla October 25, 2007