In my senior year of high school, we were allowed to dress up for Halloween, and so I thought it would be funny to dress up a girl. Most people thought it was funny, and I did too, except for when my friends and I went somewhere to eat and some dude started hitting on me. I told him I was a guy and he didn't believe me, so eventually I just lifted up my skirt. He went white and left, and I think it's funny now, but I was pretty mortified then. It's always good for a story though.