The Dude Society

An Online Magazine for Guys.

Avoid Early Group Dates Like The Plague

I want to impart to you an important lesson I learned when I was dating: Avoid group dates at all cost early on.

A few years ago, shortly after moving back to NYC, I met a girl on Match. We chatted via email for a week or two and went out on two excellent dates. I did everything right and she was totally into me by the end of that second date…

As scheduling would have it, I was slated to go out of town with my family for a week soon after, and I knew I wanted to go on another date with this girl before leaving town. We all know a lot can happen in a week, so I wanted to be fresh in her mind before leaving.

The only night we could arrange to see each other was one when she already had plans with a group of friends, but she invited me to join. Rather than encouraging her to do something alone with me before or after her other plans, I agreed to join the group.

Awkwardness ensued…

I arrive at her apartment to find the girl, her roommate, and a number of their mutual friends. I’m hardly in the door, someone makes a reference to a gay bar, and I made a joking comment like “If we are going to a gay bar, I need to get mentally prepared!”

Now, if you know me at all by now, you’d know I meant nothing by such a joke. Gay dudes are great, we typically have quite a lot common, minus our attraction to other men. However, I rounded the corner in the apartment to meet their gay friend, who didn’t know me at all but now obviously thought I was kind of a dick.

I recovered from that minor setback, we did some more introductions, and we headed out to the bar (at a trendy hotel in Chelsea). I managed to get some brief alone time at the bar with girl, and I tried to make the best of it, but it was limited.

The minefield continued…

Two of the other group members happened to be two extremely attractive, and supposedly extremely religious/conservative girls. Yet, they were dancing with each other like extras in a Lil Jon video (aka very provocatively). We were all in a tight area at this point, so I probably watched them a little more intently than I should have been. When I’m hanging out with platonic female friends in a group like this, I’m used to acting however I want, so I think my mind slipped out of date-mode momentarily. It truly was 100% unintentional.


We finish up at the bar and get in a cab back to her place (with her roommate). Over the course of this ten minute cab ride, I was trying to schmooze with her roommate by talking about a movie she had auditioned for recently. Evidently, not being cast in said movie was a very sore subject for her. Slightly drunk Jamie wasn’t so in touch with the subtleties of the situation, so I kept asking about it much more than I should have. As I remember it, I was joking around, and she probably took me seriously.

We arrived back at the girl’s place, her roommate went upstairs, and we stayed outside for a couple minutes. We kissed, and it was fine, but the palatable energy that had been there on the first two dates wasn’t nearly as strong this time around…

The Lesson

I went on the trip with my family as planned, left her a voicemail and sent an email while I was away, but I never got a call/email back. It really sucked. Ironically, I was extremely puzzled at the time. It was only after careful analysis in hindsight I realized the possible ways I had really messed this up. Never before had two dates gone so well, only to nose-dive after one more.

Were these oversights my fault? Yeah, pretty much. However, when tossed into a group date setting like this, it is really easy to f*ck up, even with the best intentions. That is my warning to you. Meeting the friends is great, when the time is right.

Do you have any awkward group date stories?

About the author

Jamie is the Founder of The Dude Society and a New York City based web designer & developer. He really likes telling people how to think, act, and dress.

All articles by Jamie »

6 responses to “Avoid Early Group Dates Like The Plague”

  1. jone says:

    do real men use match?

    • Jamie says:

      Sure. Online dating is one way to meet people that you wouldn't normally meet. You shouldn't put all your eggs in one basket, but it\'s one route to try.

      I met my girlfriend on Match, and she was a law student at Columbia at the time… so I most likely wouldn't have run into her otherwise.

  2. GM45 says:

    "so I think my mind slipped out of date-mode momentarily". The best part.

  3. Dave says:

    I love reading your blog. I am thinking about starting a blog of my own and I had a question for you. What is the rule with using pictures in your articles? If you want to promote a brand's product, do you have to get permission to post a pic of the product?

    • Jamie says:

      Speaking for this site, I either take the photos myself or pay to license them from a photo company. When it comes to using product images, typically PR reps for the brands will provide you with high res copies and essentially grant you permission to use them.

      A lot of blogs just use google images to find photos to use, and while this is widely done, it's a bad practice because often you are actually stealing people's work without permission. People think they are allowed to just use any image they want if they state where it came from and this is NOT true.

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