WINFAIL

A situation that appears to be very awesome (very WIN), but then turns to a very shitty situation (very FAIL).

Dude! Sara is breaking up with her boyfriend...but she says she doesn't want to date for a while...so WINFAIL...

by John Smith74 March 5, 2008

WINFAIL

When you get a kill in a game, and are subsequently killed immediately after, by whatever means.

"In MW2 I no scoped some douche camper, but then I ran into his claymore, WINFAIL"

by Grand Body March 29, 2010

winfail

the word winfail is used to describe those moments when someone or something fails so hard that it actually wins. winfail can be a noun but it can also be a verb too.

Anchorman on Live News: Keep f*cking that chicken!

Guy: LMAOOO WIIIIIN!!

Buddy: wow. FAIL.

Friend: Oh hoho thats a WINFAIL!

by edyStaaang September 13, 2011