What's the dumbest bet you've ever made?

A buddy of mine and his GF had been on and off for about 3 months now. They would break up and get back together regularly. This led to me putting and over/under on how long they would stay together this time around. It really got of hand and I had to buy a blackboard to keep track of the bets. On about the 5th time of this the under was coming in to much so I made the over/under on the 6th and final time a mere 12 hours. Needless to say all the money came in on the over, so I [censored] his GF and told him about 8 hours later so he broke up with her and I made a killing. He then found out about the bet and was pissed up until I bought an eight to smoke with him. She was a whore anyways.