Strip Poker! Never go all in!
We had the girls almost stripped
(Photo from Jacrews7 via flickr)
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...