I think it's a play on lollipop. She's Lolli, Boob is Pop. No idea which genius in that family came up with it.
I cut my husband's hair, I use a trimmer and don't pretend I know what I'm doing on YouTube. My husband wears hats a lot so he just wants it short and doesn't care too much about the quality. If we go somewhere, like a wedding, where no hats are to be worn he gets it professionally done.