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!"
Gene: "Nah I'm staying in tonight. I'm pretty tired."
Rob: "You going for a win-win?"
Gene: "Great idea!"
by Wolf man May 22, 2012
Get the Win-winmug. A philosophy of life where defeat is not an option. A way to emphasize an event you consider positive. Popularized by the actor/philosopher Charlie Sheen.
by DetoxTV March 18, 2011
Get the Winningmug. 
1. a sentence enhancer meant to declare that the previous statement was full of win, epic, and made by someone ripe with tiger blood
2. the act of a person or thing (never trolls) that wins
2. the act of a person or thing (never trolls) that wins
I was hitting seven gram rocks. Winning!
I'm not bi-polar, I'm bi-WINNING; I win here and I win there.
I'm not bi-polar, I'm bi-WINNING; I win here and I win there.
by HeffandAlex March 27, 2011
Get the WINNINGmug. Basically your " in it to win it" when you will go far a wide to pursue the following :
sex/booty
$$$
social status
or anything as long as your hardcore about it .
sex/booty
$$$
social status
or anything as long as your hardcore about it .
Friend 1: Damn that guy has been trying to bone me for months ....
Friend 2 : He's soooo in it to win it
Friend 2 : He's soooo in it to win it
by 12E4 May 19, 2008
Get the In it to win itmug. 
1.) When "Tiger Blood" courses though one's veins.
2.) Achieving absolute victory.
3.) Pounding seven gram rocks every night.
4.) When one is a "high priest Vatican assassin warlock"
5.) When one is using an unavailable drug called "Charlie Sheen." If one trys said drug once, the user will die. Their face will melt off and their children will weep over their exploded body.
6.) When one's brain is not from this terrestrial realm, and cannot be handled by anyone but Charlie Sheen for five minutes before the receiving party says, "Dude, can't handle it, unplug this bastard."
2.) Achieving absolute victory.
3.) Pounding seven gram rocks every night.
4.) When one is a "high priest Vatican assassin warlock"
5.) When one is using an unavailable drug called "Charlie Sheen." If one trys said drug once, the user will die. Their face will melt off and their children will weep over their exploded body.
6.) When one's brain is not from this terrestrial realm, and cannot be handled by anyone but Charlie Sheen for five minutes before the receiving party says, "Dude, can't handle it, unplug this bastard."
by Skim Shady March 29, 2011
Get the Winningmug.