One time in high school, we were playing strip poker with some girls. They were pretty hot and I had a lucky streak, so they were down to their underwear and I just had lost my shoes and socks.
Then, I got a pretty good hand (Full House, I can still remember every card!), so I started to push my luck. After I bet higher, some of the girls folded. But the one I liked was still in!
Since I had such an advantage in clothing, she dared me to bet all for the rest of her clothes. Since she was the hottest girl and I was pretty sure that I would win, I agreed.
Well, she had the higher hand: Four of a kind!
My jaw dropped almost as fast as my clothes, since they jumped all over me to strip me butt-naked! Not only was I standing there, naked, with red cheeks like an idiot. I also got a reputation as a notoriously bad poker player from there on...