shy bear Share definition Flag A shy bear is an act where you moon someone, and while you are doing this a poo pokes out (and possibly shrinks back in), like a shy bear poking its nose out of a cave. I can't believe he pulled off a shy bear behind the principal's back! shy bear by Bloopy April 9, 2005 0 0 Get merch Get the shy bear mug. Buy Now — $32.95 See more merch