Many years ago, in the pre-Daily Show years, Jon Stewart asked out Jennifer Aniston. She showed up at the date with a bunch of friends. He was bummed.

Yes, yes. That was very bad date etiquette. But not as bad as the time that I got so drunk that I threw up on the guy's shoes. I must have been cute while I was puking though, because he asked me out again. 

Question of the Day: What was your worst first date?