Ideas for an embarrassing act?

Question

My boyfriend lost a bet with me and the consequences are that he has to do something embarrassing and I get to record it on my camera. I'm lost as to what to have him do though. Any suggestions?

We're in high school, so keep it age appropriate, please.

Answer 1

Make him sing a love song to a teacher at school. Have his mom (or someone pretending to be) bring him a sack lunch at school and kiss him and use spit to clean his face. Write "just married" on the back of his car and tie shoes and cans on it and make him drive around like that for a week.  

Answer 2

Dressing up in a girl's dress with makeup and all!

Answer 3

make him get bikini wax