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.
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out with platonic female friends in a group like this, I'm used to acting however I want, so I think my mind slipped out of date-mode momentarily.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...
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?