Then he just took my money!

My first real date was my senior year in high school (sad i know!) I took this girl that I had been friends with for a while and was really connecting with to a hibachi place. Dinner was fine, and it was very expensive, more than $60 if I remember correctly. After I offered to pay with a debit card, she pulled out a $20 and put it on the table. I proceeded to take it and put it in my wallet. Seemed logical at the time, I payed for 2/3 of the meal, I was a broke high school student what can I say? As soon as I put the $20 in my wallet, I realized how weird it was that I just sort of pocketed her money. The last five minutes of the date were very awkward.

After we leave, we both head to our cars, I got a text from my friend saying she was at the restaurant and they were all almost done and wondering what I was up to. So I drove around for a minute looking for a new spot, parked and walked in. Right as I came in I hear a loud "Yeah, then he just took my money" from the girl I had just taken out. It was so awkward but luckily I'm at the point now where I can just laugh about it with her, but it was very embarrassing because they all saw me right after she said it, and there was no way to pretend I didn't hear it.

Boys Will Be Girls

I called an escort service for a date to my work Christmas party. She seemed pretty enough. As I enjoyed the party with my friends, one by one they started mentioning unusual things about her. Large adam apple, big veins. Well one of my friends girlfriend told me she saw my date in the women's bathroom. She was peeing in the toilet while standing up and pulling her pretty dress up. I quietly said goodnight to everyone and brought my date home. I guess you live and learn, saw my eye doctor, and bought a new pair of glasses. After all, I just asked for an attractive escort. I figured since I was a man, she would be a woman.

Ice Cream Anyone?

My girlfriend and I were watching a movie at her house and we where holding hands, her parents where in there too. They all got up for ice cream and i was like "be there in a bit". I couldn't get up cause of the large bulge in my pants, but that wasn't the worse part. I think her dad knew so I made sure I stayed in the chair with my legs pinched together for the rest of the movie.