1. to Fail so hard that it becomes a Win; something ridiculous, pointless and/or accidental that turns out well, or at least cool 2. an act so stupid that it's actually impressive 3. when one person's Fail is another person's Win 4. a Failed attempt at one thing that leads to a Win at something else; a mistake that works out in the end; to make such a mistake
1. Man orders size 14.5 shoe, company sends him size 1450.
2. Man thinks his house is being robbed, swallows his 200 piece coin collection to keep it safe. Fail: He wasn't really being robbed; Win: He was able to swallow 200 coins
3. Woman tries to shame her bf in public by threatening to break up with him; he actually breaks up with her
4. Chocolate chip cookies were invented when a baker ran out of chocolate powder, so instead broke pieces of baker's chocolate into the dough, thinking it would turn the dough chocolate; the most iconic cookie in the world was made by accident.
When a "fail" is followed closely by a "win". Where both "fail" and "win" hold the meaning associated with the internet meme, or slang.
I just face-planted the sidewalk and found ten dollars. Fwin!