Anyone else made an odd bet?

I’m typing this while returning from the fabric store because my
coworker said, “I bet you can’t make a full pirate costume by Talk Like a Pirate Day. From scratch.”

If I finish it and wear it on September 19, I win a Joann Fabrics gift card. I lose, she wins a Victoria’s secret one. Works out- I’ve always wanted a pirate costume.

Anyone else here made a strange bet?

I swear the following is true.
New York City, pre-mayoral election 1997. The lineup was Rudy Giuliani vs. Manhattan Borough president Ruth Messinger. I was for Rudy, and a woman I was friends with was for Messinger. There was a lot of sexual tension between us, but unfulfilled as of then. Somehow, while we were debating, the subject of her shopping at Victoria’s Secret came up. And then I hit upon my scheme. Our bet was, whosever candidate won the election, they would get to pick an outfit from Victoria’s which would have to be modelled by the loser. That is, if Giuliani won, I would pick out her outfit that she would parade around in (behind closed doors) for a full minute (naturally, I’d pick something as skimpy as possible). On the chance Messinger won, I’d have to do the same for her.
Giuliani won, and she dutifully honored her commitment - with the none-too-surprising epilogue that we ended up hitting it that nite. Afterward, it occurred to me that I would’ve ‘won’ either way - i.e. if I had lost the bet, I would’ve had to wear a Victoria’s bra & panties in front of her, & probably ended up hitting it just as the other way. Men can be creative when properly motivated.

OP, that is one epic bet! I salute you.

Hmm. I don’t seem to recall making any odd bets. Maybe it’s time to start.