lolipop Share definition Flag When a girl is so skinny making her head look too big for her body so she looks like a lollipop. Caroline is cute, but shes a borderline lolipop, i need a girl with a little meat on her bones. lolipop by minagastrostefano March 7, 2012 0 0 Get merch Get the lolipop mug. Buy Now — $32.95 See more merch