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Something everyone loves and wants to have/achieve.
Person: He is such a Win-win
Win-win by emilie_thesv February 2, 2021
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!"
Win-win by Wolf man May 22, 2012
Woman lays belly down so her head is near the edge of the bed. The male places his penis in the woman's mouth, so that the deeper he gos, the harder he can press on the ladies back. The purpose being that they both get what they want. She gets a back rub, he gets head. The deeper he gos, the better\harder he presses on the back.
Her: baby, can I get a backrub?

Him: I've got a Win-Win for ya, dear.
Win-Win by Piratevalandi May 10, 2018
Describes the mutual benefit and result when a brave human shares their life story.

The human feels more connected with themself.

The other humans feel more connected to each other.

The web of humanity continues to grow through individual life stories.
Brave human shared their life stories to benefit future generations while also discovering personal reflective gems - it was a WIN-WIN.
WIN-WIN by the WIN/WIN September 6, 2020
Describes the mutual benefit and result when a brave human shares their life story.

The human feels more connected with themself.

The other humans feel more connected to each other.

The web of humanity continues to grow through individual life stories.
Brave human shared their life stories to benefit future generations while also discovering personal reflective gems - it was a WIN-WIN.
WIN-WIN by the WIN/WIN September 6, 2020
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?
Win win by jamesbrown May 1, 2003
More from Urban Dictionary

square grouper

Nickname given to bales of marijuana thrown overboard or out of airplanes. Origin is reportedly from members of the US Coast Guard in the area of Southern Florida.
"Base we've got some square groupers floating outside of Miami harbor."
square grouper by slipsheet November 6, 2004
Word of the Day on October 7, 2026
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