Home > Bitching, Dating, New York > The Time I Had the Worst Date Ever

The Time I Had the Worst Date Ever

September 28, 2011 Leave a comment Go to comments


We met in a bar. He could tell I was Jewish from across the room “because of the nose,” he was quick to point out. I was drunk and decided that though he was awkward, at least he had balls.

We went to a nice lounge bar of his choosing a few days later. Things immediately started to go south, and I decided I’d give him three strikes.  He managed to use them all within the first hour.

  • Strike 1: Discussing the eventual birth of our first child.

“So, would you let my family in the birthing room with you? I know some girls would be weirded out by that, but I’d really want my family in there with us, you know? Witnessing the miracle of life. How soon do you think we’ll be having kids?”

Pro: He’s close with his family!

Con: Way too close. Like in a “he’s going to kill them all one day” kind of way. And the first 10 minutes of a first date is not the time to bring up graphic vaginal birth.

  • Strike 2: Talking about his “awesome” threesome.

“It was crazy, but at least I had two girls and not some dude, am I right? Sometimes it was hard to figure out what to do, though – I mean, who sucks what?”

Pro: Adventuresome! At least sex wouldn’t be vanilla.

Con: Dude, I am not impressed by your threesome on the FIRST DATE.  Or EVER.

  • Strike 3: Can I tell you about my sexual fantasy?

At this point, I knew I was never going to see him again, so I said SURE, let’s hear what comes out of this fucking mouth of yours.

“I’ve always wanted to have sex while watching Star Trek. I don’t really care which series, but I’d prefer not Deep Space 9.”

After the threesome, I can’t say that I was expecting that.

Now, I’ve been raised a good little nerd. My dad has a home theater in our basement with Star Trek posters on one wall and Star Wars posters on the other (he just couldn’t choose!). But mixing sex with it just isn’t my thing.

I hastily made an excuse and got out of there, but he proceeded to call and text me daily for the next month. Yeah, not creepy at all.

  1. September 28, 2011 at 11:51 am

    HA! Fabulous! But my motto – what doesn’t work sure does make one hell of a story! 🙂

  2. October 3, 2011 at 8:11 pm

    i never heard all of these details before. hilarious!

  3. August 27, 2012 at 5:23 pm

    EEHEEHEEHEE! Bad date stories are my SECOND FAVORITE!!!!
    I think you’re pretty charitable for lasting to strike three. I’m pretty sure I’d have been outta there once my vagina-for-view topic was on the table.

    • August 28, 2012 at 11:09 am

      I was so horrified that it was like looking at a train wreck. I stuck with it just to see what the hell he would say next. But yeah, vagina-viewing is not my favorite topic of conversation.

      • August 29, 2012 at 10:31 pm

        My BFF and I made up a checklist for just such occasions. If I still had that list, I would definitely add “Date mentions his family looking at my vagina” and checking that one would totally have ended the date.

    • August 30, 2012 at 10:41 am

      Fair enough – there are a lot of things that should probably be on a checklist like that.

      Also, I tried to go to your blog, but it’s password protected 😦 Wah wahhhhh.

      • September 5, 2012 at 6:22 pm

        My blog? Yeah, it’s not alive yet. I mean, I’ve got my personal, private, back-room blog where I collect stuff I need to use later…but my upcoming blog will go live in about three weeks. I think you can follow it now, though, if you really felt like it. That part is open now…at least, it should be.

      • September 6, 2012 at 3:23 pm

        Nice, looking forward to it going live!

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