Scenario: intelligent woman with undergrad degree for a prestigious university, witty and a bit quirky with a very dry almost English/European sense of humor.

I have thought about the different angles thing. Had forgotten that I live in an area where men outnumber women by a lot, and they really tend to be interested in getting in people’s pants.

The problem is, I don’t think of “dating” as seeing how fast one can hookup. While I am not quite 40, I grew up in a very conservative area, and was mostly raised by my grandparents who were of a very conservative era. Went to undergrad/grad school at a very conservative (for a university) institution in the South. My idea of “dating” involves more courtship than what seems to be today.

However, I avoided dating simply because I had observed dynamics in the family that I didn’t want to repeat. Decades of that mindset let me to shun social events, etc. I put work first, and while I have become far more financially successful than anyone in my immediate family, I became socially inept.

Plus, I tend to be a blunt instrument. Finesse tends to not be a strongpoint. The old line when all you have is a hammer, everything looks like a nail kind of applies. If I like something, I say so and if I don’t, I say so. Perhaps I was a bit hasty in expressing that I liked her, which she probably interpreted as me just being after sex. The ironic thing is, I am blunt enough that if I were truly after sex, I would ask. Heck, I have been celibate for almost 40 years, a period of courtship is nothing.

I also thought too that there could be an issues with whether or not she could date me due to the intersections with our careers. Though it would have been nice to know if that was he concern.

I know that she had a recent ex. They had been in a live-in relationship. He and I have some similar interests, and I am wondering if that triggered bad memories. I don’t know what happened, but guessing it was ugly.

After me asking her to date, she has really withdrawn from her co-workers and myself in general. I have seen her cross the street to avoid contact with people, and she seems to rush right back home to the tiny place she is trying to refurbish. It is tiny home from the 1950’s and I had warned her about putting more into it than she would ever get out. Now thinking that may have been a land mine.

Earlier this week, she approached me about some gardening stuff and wanted to meet later and Thursday she decided to come to my office with a non-urgent question and talk. Then, when I emailed her about how her house project was going I got no replies. When I was talking with a group of her coworkers after hours, she went to the other side of the street. I don’t get that at all.

Assuming that any ethical issues could be resolved, thoughts on whether this will ever develop into anything? I deeply regret not starting with lesser “interests” first to work on social skills instead of going for the gold with “tin” skills. Where I live, finding a combination of education, intelligence, etc. among single women is rare. Feels like I squandered a great opportunity. There is the somewhat cynical school of thought on people changing beliefs only when the pain of not changing exceeds the pain of changing. I had gotten used to the low-level pain of being perpetually single due to beliefs I had about relationships. Work could cover it up, and I put in nasty hours.

I developed a reputation for being a tough, hard-nosed prosecutor who specialized in non-victim crimes (except homicides). I made it plain that I was not particularly empathetic, etc. While it was nice to go into court and get an oh expletive reaction from defendants and their sob-stories, I did not realize just how scary the absence of empathy can be to people. Eventually, I failed to heed the warning about fighting monsters, and got to the point where I had convinced myself that I really did lack empathy. My reputation I am sure spread. I had never thought about any negative consequences of such a reputation.

However, this situation was a pain I had never felt before, I couldn’t cover it with work like I did with the death of my father. It was a combination of grief and a realization that as I was nearing mid-life, I couldn’t even keep a relationship going past two lunch dates. Even now about one month out I still sometimes cry thinking about it.

So, I started looking into such things as emotional intelligence. I learned that the perception of a lack of empathy is a big red flag in relationships. I took a look, and thought about my reactions to certain things and realized that maybe I do have empathy at some level. Sadly, a bit late.

At one point, there was something between us; I now recognize some of the cues that I had missed and we used to talk about things.

Can’t go back have a do-over, but is this salvagable or is it well and truly dead?