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!"
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?
When a female performs fellatio on a male while he consumes a nice juicy steak.
On March 14th I better get a win win.
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..
When you beat a player with ease and they rage.