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Humiliation Bets

I would suggest for him to take the broom and to walk on it on the street like on the horse, it would be funny
Make him go to a store that sells condoms and make him ask where he could fit the condoms, much like fitting clothes. That'd be hilarious!
Not a humiliation bet but it fits this thread. When I was a kid we used to chat in irc. I went to gaming club with my friend and we started to chat. While I was using my regular nickname I also started another instance if MIRC with girl's username. I started to chat with my friend( who was sitting behind my back by the way) and he didn't check my irc address it seems. I talked him to date at the center of our town and he agreed. He seemed in a hurry and he just told me "I need to go". After this I paid my bill and followed him to the center and he was sitting here and waiting. I just told him "It was me, do you think she will agree so fast on a date?" and he started to scream things like motherfucker and idiot but after this he was okay and we laughed it out :D.