Me: 37M, athletic (6'4'' 192lbs), zero experience with women (multiple reasons), introverted, somewhat socially awkward with a bit of social anxiety sprinkled on.
Registered on a local (I live in Europe) "serious" OLD site, got "selected" by a 35F. I'm a tech person, have a good career in an IT field, well established, but my life is otherwise pretty uneventful and basic (but I like that, very peaceful). She has WAY MORE life experience - well travelled, studied in multiple universities, has a phd in humanities, does research work, produced/directed 3 local documentaries, very knowledgeable about arts and culture, much larger social circle, had previous relationships, etc. On paper, a polar opposite of me in terms of interests. We both agreed we have these differences but still decided to meet for a walk. Quite a handful for a first date ever, huh?
However, it wasn't that bad and was even enjoyable, we spent 3h talking (she was talking most of the time). Nothing exploded, no injuries, just a couple of awkward moments. She's quite nerdy too, but a very good communicator and interesting person. I liked her brain a lot, but I wasn't sure if I wanted her sexually. She said she was sitting on the fence also. Since nothing bad happened, we agreed to another date to see if things would start rolling.
We went to a concert after a few days, had a good time. Had 2h+ of conversation afterwards which was nice once again. She had a scheduled meeting very early next morning but for some reason she stayed to talk with me instead of going back home shortly after the concert (she must have sleept like 5h max that night). We walked back to her house (quite a distance) talking about stuff and she was walking her city bike all the way (she didn't allow me to do it) even though she could have simply ridden the bike home by herself. Because of that, I assumed at least some interest here, but at the end of the date she said nothing really changed since the first one. My sexual attraction towards her hasn't inreased either. She said she wouldn't mind a third date, however I'm starting to have my doubts about this especially since it could only happen after at least a couple of weeks.
I feel disappointed about my attraction towards her. I really like her personality (she's introverted too), very self-sufficient, well educated on many topics, no pushover, overall seems like a very decent person. We also agreed on the things we would find important in a relationship. I don't find her face particularly appealing unfortunately (her body is fine), but I'm no Brad Pitt myself either, so that's that. If she jumped me, I wouldn't mind, but I somehow don't have the urge to jump her myself.
There was no sexual escalation during the two dates (no touching except handshakes, very little flirting). She did not send me any signals (or I missed them), so I did not move forward. If I knew she liked me, I probably would have.
I'm also confused about her communication - if she feels no attraction towards me, why stay late and agree to further dates (I did not pay anything for her, so that motive is out of the question)?
Should I go on the third date with her, or should I end it now? Two dates and it doesn't seem like a great start on both sides, so maybe that's a sign we should stop? If I go on the third date, should I try to escalate anyway (even though I don't see signs of her wanting that) or should I wait more? Can I even expect further dates to help build attraction if it hasn't happened yet (it could very well be that feelings take longer to start up when you're older, I'm not sure)? Am I missing something here?
If I end it, I'm pretty sure I won't meet a woman of similar intelectual capacity as her any time soon though which is a shame.
Any advice?
