Question of the Day: Bad First Dates

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Jennifer Aniston
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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?

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8 thoughts on “Question of the Day: Bad First Dates

  1. Same as Wendy. My wife, who had a long term boyfriend at the time, seems to think that we were dating for about 3 months before I had any idea that was what we were doing.

  2. My worst first date: near the end the man told me that while he wasn’t attracted to me, he thought I had something to teach him and would like to be friends. Blech, but really not that bad after all.
    I was on somebody else’s worst first date, and it was definitely worse than mine. It was a group date, a bunch of unattached individual people except for one couple who’d come together on their first date. We went to a brewer’s festival. About midway through I detoured briefly from the group to get a sausage on a stick and the man from the first date said under his breath (but we all heard it) “Oh good, not a vegetarian.” Later while we were standing around waiting for public transit he asked me whether I was planning to have more children.
    I think his date figured out he liked me better, and she was pretty awful to me after that.

  3. Took a date to see the Big Bird movie, Follow that Bird. I kid you not. I cannot believe what a strange kind of dork I was. (Second worst: Taking a date to see George Lucas’s Howard the Duck. I was pretty bad at choosing movies for a long time there.

  4. In college, extremely overweight and self conscious at the time, set up on a blind date. Mutual friend thought we’d get along great because we were both…you know… overweight. Nice. I decided to wear a blue and white horizontal striped top (I know, I know) because it was the newest clothing item I owned. It was probably a size 1X or something.
    Anyway, blind date rings the doorbell, and I open the door to find a large man wearing the exact same blue and white horizontal striped shirt! So there we were, two people, both very heavy, wearing matching, unflattering shirts in public on our first date.
    Horrific.
    Never heard from him again, thank goodness.
    For the record, this was over 20 years ago and I’m now nearly 40 lbs lighter. 🙂

  5. On our first date, my fiance and I went to a mexican restaurant, and I order something I forgot the name but it was a huge plateful of fattening food, like a lot of cheese, baked beans, and a lot of steak and bunch of other things..many months later, he told me on that day, he didn’t remember much else about me but how much I ate, I ate a lot more than he did and I tell ya he’s very famous for eating a lot among our friends.

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