Tell us about the most embarrassing date that you have ever done?

I had many in my day.

In high school, I took this super hot chick who was already out of school to a concert - she was such a dream to me then. She is STILL a world class beauty today. I had my mother's raggedy car and it died in the parking lot as we were about to leave after the concert. She saw some people that she knew and left with them while I waited in the cold for a tow truck. I was humiliated and disappointed. That was the early 80s and I am still embarrassed.