A few days ago I was thinking of strange bets people could make, and I came to one that totally confused me.

"I'll bet you $10 I lose this bet."

I sat there for several minutes trying to figure out how that would work before I gave up. I've also said it to several people and they just stand there not moving for a while then look at me with a confused look on their face. Nothing else I've thought of has even come close to being as confusing as that.