I wanted to share my latest OkCupid experience. Since 2006, I've met probably around 50 OkCupid people, with a few more from Craigslist and Facebook. The results have been dismal, though (~10 k-closes and less of everything else) -- I'm really terrible at in-person interaction, and most of the time people turn out to be completely different in person than online (not just visually but in the personality and chemistry). But I've gotten some advice from here and I put up some better pictures so people have been responding more than usual.

It started with the following exchange on Dec. 23:

[A few initial lines omitted for anonymity]

(4:53:04 pm)me:how are you planning on getting through christams

(4:56:33 pm)her:having dinner with friends, then going clubbing

(4:56:35 pm)her:you?

(4:57:53 pm)me:clubbing? there are clubs open tomorrow?

(4:58:07 pm)her:there's a big Jewish party

(4:58:12 pm)me:oh that

(4:58:15 pm)me:that's tonight, right?

(4:59:17 pm)her:I think both nights

(5:00:10 pm)me:have you been to them before

(5:00:22 pm)her:nope - have you?

(5:00:25 pm)me:no

(5:00:45 pm)me:I was considering it but I think it might be somewhat anti-arousing

(5:00:53 pm)me:as jewish social events tend to be

(5:01:10 pm)me:but I want your full report

(5:01:16 pm)me:I have to go to whole foods before it closes

(5:02:09 pm)her:happy hunting!

I saw things were going pretty well, so I cut the conversation short. Then a few days later:

(9:25:31 pm)me:so? how was it?

(9:25:50 pm)her:it was kind of entertaining, actually

(9:26:04 pm)her:but that may be because the purpose of going was my friend's bachelorette party

(9:26:38 pm)me:hmm so you brought your own party

(9:27:04 pm)her:I think we just brought the right mindset

(9:27:25 pm)her:so your experience with such things has been dismal?

(9:27:57 pm)me:I just think jews don't generally know how to party

(9:28:10 pm)me:there's a reason why they talk about catholic school girls

(9:29:33 pm)her:I thought those reasons crossed religious boundaries , like short skirts and abundant guilt

(9:30:00 pm)me:hmm well I think catholics have more of that

(9:30:05 pm)me:supposedly

(9:30:24 pm)me:anyway, every jewish party I've ever been to has been quite proper

(9:31:15 pm)her:that's a shame

(9:32:22 pm)me:so your friends have abundant guilt?

(9:33:35 pm)her:some do, sometimes

(9:34:11 pm)her:I don't find that it correlates significantly with religion

(9:34:15 pm)her:do you?

(9:35:22 pm)me:I think it's more that people who throw jewish-themed parties don't have the right priorities

(9:35:45 pm)her:you mean they care too much about propriety?

(9:37:02 pm)me:they just don't have enough impropriety in them

(9:39:10 pm)her:that does sound dull. I feel like apologizing on their behalf :)

(9:39:17 pm)her:(= abundant guilt?)

(9:41:54 pm)me:hmm, well, I think I would only accept such an apology in person

(9:44:05 pm)her:you'd have to really like apologies, in that case, since I'm not back from break for another week...

(9:45:00 pm)me:well, let's hope you're really sorry, then

(9:46:34 pm)her:words cannot express the depths of my contrition

(9:47:36 pm)me:well I'll let you think of better ways

(9:47:44 pm)me:ttyl :)

(9:50:07 pm)her:bye! enjoy the snow, if it's not too cold and proper for that :P

Again I decided to cut the conversation short since it was going well. A week later, she sent me a message:

Jan. 4, 2011 – 8:53pm I'm back - fancy some contrition for the excessive propriety of the Jewish scene over some tea?

Jan. 7, 2011 – 11:19am OK, let's do noon tomorrow at X.

Jan. 7, 2011 – 4:54pm X sounds good, but I can't do noon tomorrow - how about sometime Sunday night?

Jan. 8, 2011 – 8:24pm Ok 8pm?

Jan. 9, 2011 – 11:05am 8 works. See you then.

So far, so good. I'm rather proud of this so far. Then things went downhill. I arrived at X, a cafe. She was already there. I asked her what she had ordered, then I ordered. I should have done kino right away but I missed the chance. She didn't really smile or try very hard to keep the conversation going and neither did I. The whole interaction was very low-energy.

Then we sat down. Unfortunately we sat across from each other so we couldn't do any kino again.

She asked me what awkward experiences I had had lately. I said that I met this OkCupid girl at a cafe, meaning her. I meant to be teasing her. We exchanged some more awkward stories. At one point I tried switching to "smooth stories" but this didn't work out. There was some mildly entertaining banter. She had said her drink was girly and asked me if my drink was manly enough. I said that it was, it was Chai, but it tasted just like black tea with milk. She said milk is not very manly. I said that it was dragon milk.

I tried a few things, including the "awkward silence" thing in the Craig Ferguson clips that intjpua linked a while ago. The first time I did it, I didn't warn her, and just looked at her smiling mysteriously. She broke it, so I was happy about that. I should have steered the conversation in a more sexual or risque direction, but there were some old ladies sitting next to us, and the place was so quiet they would certainly have heard anything I said (this definitely didn't help me).

Unfortunately, the "awkward" theme sort of took over. I had meant to take it as a joke, but it increasingly became clear that to her, it wasn't. She said at one point that all of her OkCupid dates had defining characteristics, but awkwardness was the defining characteristic of this one. That hit a bit too close to home. Also too close to home was when I said that I don't have relationships and she asked if it was because I'm too awkward. Also she gave me an opportunity to escalate by saying that "I have to do something even more awkward now" but I didn't.

Once we finished our drinks, I suggested we leave. She said she was going to stay because she was meeting someone else close by in half an hour. This was a bad sign, but I said that in that case I would stay a bit longer since I had meant for us to walk together. So we continued. The subject of interacting with cats came up and I said that it would be difficult to walk my cat because he would probably just lie down and be impossible to move. She said that perhaps I could with leather gloves. I said that it would just be rude to the cat, and if someone wants to do something, I prefer not to stand in their way. She said, "What if that conflicts with your personal interests?" I said, "Then . . . oh, well." She said, "That's very . . . kind of you." I thought that might have been a positive moment despite its inherent beta-tude, but I believe the whole interaction was completely sunk by then. Another positive moment was when she said she doesn't go on too many OkCupid dates because most people are not interesting. So again that shows that I did the online part pretty well.

I finally got up and said that it was time for me to go, and she started to put on her jacket as well. I thought that she would walk out with me, but she remained sitting and said "It was nice to meet you." Perhaps she was worried I would try to hug or kiss her, in which case it was quite insulting. So then I just walked out. As I walked home, I felt fairly terrible about the whole thing because in the end it seemed clear that she was just dissing me the whole time. I probably should have just walked out a lot sooner.