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originally used as a normal word in phrases such as "we win the championship" "I will win this trophy" etc. But since the rise of online gaming, it has been used more and more out of context, and has developed into a nerd slang term.

Instead of using proper grammar, these geeks say "win" every time they see something funny or amusing. (See example).

I do not know how this is a "cool" word, but like I previously said, it's nerd lingo.
Nerd after watching a Naruto marathon: This show is win!!
Win by doggyboggyboi July 28, 2009
a way to say epic without people wanting to shoot you.

on the internetz the exclamation mark is needed when stated by it's self; when used in a sentence the exclamation mark is optional

when the word is used irl it should not be said by it's self.
unless your friends are hip and know you're not saying "when!"
"dude i got two toys in my kids meal!"
"fuckin win dude!"

facebook:
gr3g- ii got 2 toiyz in mi kidz meal nigga!
RalF- win!
win! by GregS. December 4, 2010
convincing a girl on webcam to show her vagina
Dude, i was watching bootyshaker69 last night and i got epic win
win by douchebag1918 October 17, 2008
When an action is done that is so mind boggling Win, one must stand off to the side, and give a round of applause. Most common when someone completes a task at over NINE THOOOOOOUUUSSSAAAAND!
Jack: Hey, I need you to hack the CIA.
Mila: Alright!

**FIVE HOURS LATER**

Mila: Well, I did it...
Jack: Good, good, what did you do to them?
Mila: I actually hacked the Chinese so they would think that the CIA hacked them. Thus causing a third world war.
Jack: You miss, are made of Win. I applaud you.
Win by Hellspam January 3, 2008
win- (prefix) Added on to a word, usually a noun to describe the level of win, or awesomeness the word has.
"hey lets go to swagats. mmm win-dian"

"this chicken tiki masala has a lot of win-namon in it, mmm."
win- by Thenameisbam December 30, 2007
Someone who has a nice home shaved mullet and is just straight up steezy... usually a guy named andrew can be win.