A phrase that is linked to playing the wild card in the Mattell card game, Skip-bo. Also refers to hitting on a girl or telling a girl a really bad pick-up line.
Josh played a Skip-bo and won the game
"Josh, play a Skip-bo!"
"OK!" Josh walks up to woman and hits on her.
"Josh, play a Skip-bo on that one!"
"Alright" Josh walks up to woman and tells her a really bad pick-up line.