Top definition
A game you play with a female of interest to break the ice. It involves walking up behind the girl while she is seated, pulling your peens out and setting it on her shoulder. When she turns around in disgust, you should look at her with total confidence and say "That's right."
Matthew: Dude, I went for it. I went over to Ashley's cubicle and played Guess What's On My Shoulder?

Adam: Super Sweet. Did it work?

Matthew: No, she hit me.
by Woo Yeah Nester November 03, 2010
Get the mug
Get a Guess What's On My Shoulder? mug for your bunkmate Rihanna.