Worst Ever First (and Last) Date
This was on The Tonight Show September 7, 1999
Jay Leno went into the audience to find the most embarrassing first date that a woman ever had. The following won.
She said it was snowing and cold and the guy took her skiing. It was just a day trip. They had never been out together before.
The day went OK until they were coming back that afternoon. They were driving home and she suddenly had to pee urgently, but still at least an hour away from civilization. She asked him to stop at a gas station, which he tried to find for an hour without success. She finally asked him to stop the car so she could squat beside the road.
They stopped, and she went out, pulled down her ski pants and began to pee. She was on snow, so her footing was insecure. She leaned back against the rear fender for support. Her date was very much a gentleman, and looked the other way.
She finished peeing but suddenly realized her warm butt had stuck to the fender. She was trying to address the problem when her date rolled down the window and, trying not to look, asked if everything was OK.
Mortified, she had to tell him what had happened and asked for his help. He came around to her side of the car and, suppressing laughter, assessed the problem. After a brief discussion, they agreed they needed something like warm coffee to free her butt from the fender. As the thermos was empty, they reluctantly hit upon the same solution.
While she looked away, he unzipped his pants, aimed strategically, and peed her frozen butt from the fender.
Neither said another word for the rest of the ride home.