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1.
1)A winstake is what happens when you make a mistake (usually during a conversation) that turns out to be a total WIN.

2) A mistake that turns into something totally hilarious and hence forth called a WIN.
Abe: hey how are you?
Lincoln: could be better
ABE: why you could be doing better?

Lincoln: dick :/
Lincoln: sick*
Lincoln: xD
Abe: LMFAO
Abe: XD
Abe: dude that was a total winstake!
by trini tisha March 13, 2011