winghole Share definition Flag a wingman that has sex with the girl you were trying to hook up with. I went to the bar with my main wingman and we started hitting on some girls, by the end of the night he took my girl! What a winghole! winghole by jayhawkrules January 11, 2010 0 0 Get merch Get the winghole mug. Buy Now — $32.95 See more merch