Can we add moderate fails to spice things up a bit?
When I was young, I couldn't use the bathroom, so I went outside in the dark to piss, but forgot to hold up my shirt. I pissed all over it, and walked back in with a huge wet spot on my shirt.
I was once talking to some girl at a party, when she suddenly threw up on me. Had to party shirtless.
The biggest fail is probably the fact that I've been circumcised three times. Or, well, had my **** cut in with medical tools three times, all in relation to said circumcision. The other sounds more impressive somehow.