A winsome is when you are having sex with
two or more other
people and you are the ugliest person in the group. Therefore, the
people you get to have sex with are the hottest ones in the group.
Person #1: I had a great winsome last
night with
Deb and Vi!
Person #2: But they're way out of your league.
Person #1: Doesn't matter, I
still won!