I got a pretty good one:
My junior year in high school (this was just over two years ago) I had grown a bit of a list of girls I could hook up with on will. The only problem was keeping them all on the down low. High school is the gossip equivalent of a keg of TNT, one little light is all it takes to set everything off. I had to take precautions to make sure that everything stayed hushed, such as recording all these girls in my phone as Jackie1, Jackie 2... etc.
Anyways, one of the girls on this list is really trying to get serious with me. Don't get me wrong, she was decent looking, a solid 8, but was dumb as rocks (which had been a bonus for me for awhile.) There was no way I was settling with this girl. She asked me to go to the movies with her one night, and I told her I had other plans. There was no way I was paying money to sit around with this girl, when all I wanted to do with her were free.
In reality, I had already made plans with another girl that I WAS trying to get serious with... to go to the movies.
So I show up to the movies with my target, buy two tickets, turn around and literally three inches away from my face is the girl I had just blown off.

Apparently she had peeked at my messages while I was sleeping in class (a trend that has followed me to college) and saw all the messages from "Jackie's" in my phone.
She is there with her best "gay" friend, and boy is she angry. When she started speaking, I got that "Well, I'm fucked" feeling. Her voice sounded like it would blow at anytime, but she kept it in check as she asked:
"Which Jackie is this, Jackie number 3 or Jackie number 4?"
I look at the girl I'm with, who can already start to put together what was happening (she was actually pretty intelligent, which is why I was taking her seriously.) My night was screwed, my date was screwed, and come next monday my situation had hit every social circle I was in. The guys thought it was awesome, and the girls typically just laughed and called me a "man whore", but not all the girls...
In the end, I only kept one Jackie on my list, just because she went to a different school. That isn't to say that I didn't find a way to make this swing in my advantage much like Phate did. I ended up dating our prom queen as a result of the social proof that was left in the wake of my epic disaster. The only problem was she would not give me any intimacy until we were officially dating. Haha, man I miss high school!
-Dr4ma