Deliberate Dating

As I was sitting at church, a friend sat down, interrupted a conversation, small-chatted a sentence and said "you should ask out so-and-so. Will you?" all commitment-pattern style. Since I was mid-sentence, I acquiesced.

I asked out so-and-so and the date went well. This guy was an excellent conversationalist, very witty, charming, and about too many inches too short. Regardless, I noticed that this was good for me - to ask out a guy that wasn't on my radar and not take life so seriously. I paid more attention to how I was behaving as a date instead of analyzing and monitoring at-the-second updates of his behavior and my subsequent attraction.

Therefore, since I am addicted to goals, and since this seemed good for me, I figured I would tell myself that I had to go on 4 more within 3 months. I had to do the asking.

Date 2 included two huge pieces of pie from a dessert shop. I had just recently interviewed for a new job and was talking about the need (if I got the job) to be living near like-minded professional people. As I was talking I was analyzing myself and thinking "now is NOT the time to fantasize about my future life that doesn't include this person" but the train wreck was already happening. The next terrible thing I did was bring up school. I've since then learned to NOT explicitly talk about education. There was no way to stop the words and awkwardness that was coming out of mine and his mouth when it was happening! He got (or so I felt) somewhat defensive about the mismatch of our career trajectories. Conversation was good other than the times that I was being super awkward. I also made some rookie moves in terms of scheduling, things that I'll remember when guys who ask me out do the same thing. This ended in a car hug and no subsequent date (mutual unstated agreement).

Date 3 we met up at the place where we were going to go to a concert. That's the only part that went ok. The rest was kind of a disaster. I had tried unsuccessfully to get out of dinner, but he kind of insisted. Unfortunately dinner didn't settle with me, so I was fairly uncomfortable. Then while on the date, I dropped my phone out of my jeans back pocket in the toilet, immediately grabbed it and turned it off and was mildly concerned about it being broken for the entirety of the rest of the date. (I never told my date that this happened.) I thought the concert was going to be an indie type of thing where everyone's kind of dancing/standing but instead it was a super intimate seated setting where they did a bunch of the numbers in a remixed jazz acoustic style. I liked it, but again, was concerned that I'd told my date bad information so that he was having a bad time. To end it all, I got back home probably at midnight or so, and I had to leave for a flight at 6 am the next day. This date ended with a successfully unawkward hug, but awkward avoidance ensued for the next few months.

Date 4 came out of a breaking of my rules. I was at a good-bye party and this date suggested we "hang out." I kind of took advantage of the situation, counted it and scheduled a time immediately. "Hang-out" left me with a vague agenda of whether or not the date was a date. We ended up going to a sports game, in which I was entirely paid for and treated to great seats and a super game. However, the ambivalence I was left with from the terms "hang-out" left me with only a little guilt at meeting up with a friend and his wife who were also at the game because they happened to be in town. Since this couple is probably in my top 5 of couples, I explained to my "date" that I'd probably just meet up with them after - thus non-obligating him to drive me home. However, the game 1/2 way rained out and while everyone left my friends came over and met up with us for the last half of the game. I was fairly aware that I'd kind of inadvertently third-wheeled him, to which, I felt terrible, but justified it by referencing the ambivalence of "hanging out" as the posturing for what ended up being a date. This guy and I have no change in our relationship before or after the date.

So finally, with my deadline coming up, I realized I had almost made it to my goal with just one date left. I ended up asking out a friend who I knew fairly well and besides, he'd just broken up with his girlfriend. Date 5 was probably my most successful date. I felt really comfortable and happy. The only thing I did that was awkward, was when I got nervous and vulnerable and in defense mentioned that I'd asked him out since I needed one more date. We recovered from the statement, but I realized then that when I get nervous I'm a romantic self-sabotager, which I feel like is good to be aware of. This relationship has probably eroded just a little, however, we both moved to different locations and our lives look really different than they did then anyway.

I learned quite a few things from making myself be really uncomfortable and doing the asking. It gave me a pretty good perspective. I don't know that I'll do any asking any time soon, but I will try to remember to think about how I am behaving as a date, instead of solely analyzing their behavior. It's actually been nice too, to be asked out on dates since then, and feel confident that I am a good date by this point. It took 5 dates to do it, but I'm much more comfortable than I was dating 6 months ago.