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!
Guy: LMAOOO WIIIIIN!!
Buddy: wow. FAIL.
Friend: Oh hoho thats a WINFAIL!
by edyStaaang September 13, 2011
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 6, 2008
by Grand Body March 30, 2010