The August Dating Challenge

In late July, I challenged myself to go on one date a week in the month of August. I didn’t think I would have enough options to go on that many dates, but I started on July 31st (I decided that counts) and have miraculously been on one date a week since. I have had no luck with the OK Cupid emails I am sending, but three guys emailed me that were not so bad, so I gave them a whirl. They were all very different.

We start with British Johnny. British Johnny was 6 years older than me and sold himself as talking like the gecko in the insurance commercials (I like that gecko). He seemed like an interesting guy, but my gut told me he was to formal, serious, and geeky for me. In an attempt to determine whether I am ruling people out for the right reasons, I decided to go on the date.

The date confirmed that I would have been correct to rule out British Johnny. Nice guy, smart, and has done lots of interesting things (for example he just wrote a book on esoteric wisdom), but not a good match for me. He was visibly despondent when I told him there would be no second drink. I was surprised to learn at the end of the date that in his first week back online after many years, he had 5 dates booked from the 7 emails he sent. He also mentioned during the date that he met his first wife on his first online date ever. Go British Johnny! I am sure he is doing just fine.

The next week, I went out with “suburban Jewish guy”. I don’t usually go out with guys from the suburbs but I liked his profile and we had a bit of a banter going via email so I decided to be open to it. This date was very interesting. We had intellectual compatibility and a much deeper level of conversation than I have on most dates.

During a conversation about expectations and being open, “suburban Jewish guy” told me that I seemed very shut down at the beginning of our date and that he liked me much more after my second glass of wine. (I am definitely more fun after two glasses of wine. Who isn’t?) I explained that I was very shut down for two reasons (1) I have opened myself up twice in the past year and been hurt pretty badly (2) I don’t like hurting other people and I don’t want to seem interested and lead someone on unless I am sure I am interested. (A third reason, that I did not mention, was that he texted me from his car as he drove by looking for a parking spot to tell me he thought I looked cute. This was a bit much, so I was preparing for the worst.)

He explained that me being shut down makes the other person put up their guard and makes them not interested in me. He also theorized that I am so busy keeping my guard up, that I am not really open to seeing what may be interesting about the other person. This was all true and made me realize that if I am going to do this dating thing, I have to be more open. It was actually a very emotional conversation for me. It felt a bit like a therapy session.

Although I was not really attracted to “suburban jewish guy”, I appreciated the intellectual compatibility and his perception and self awareness so I agreed to walk with him a bit after the date. When we got to the agreed location where we would part, he asked if I wanted a second date. I responded with “yes…I think so” (this was the “not so attracted to him” and “still pondering this open thing” part of me answering). He then leaned in for a kiss which I was not feeling at all.

In the spirit of being open, I did send a follow up email the next day saying I was interested in a second date and hoped my ambivalent response did not put him off. There was some text messaging (which was actually a bit weird and made me even less interested), but I think ultimately there was ambivalence on both slides and it kind of died off.

Then I got distracted by the sommelier which turned in to date #3. I will tell you about him tomorrow…

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