Could do coffee or lunch, assuming that I run into her again. In any event, she seemed more interested in a law student who was interning than me, so, eh… Don’t fully understand, but he is obviously younger than I am.

Have also discovered that I really have a happiness problem. Found a book called learned optimism. Will have to read it.

I hear you about changing living situation.

I don’t like to discuss finances when contemplating a relationship. However, my salary is at least public record, so not like I can keep that secret. I know how some folks advertise their status, but that’s just not me. Heck, I still drive the 2009 Camry I bought back when I started this position.

Feels a bit strange to even contemplate such an age difference. Was refreshing to see somebody who seemed to have a sense of direction.

She worked in a city about 40 miles from where I grew up. Would see her mostly on weekends. Would travel sometimes, mostly to IL and MN area. She tends to think that men are inherently unreliable, etc.

She and my father divorced way, way back when. Did not know much about him, other than some periodic contacts. Usually I didn’t go to the right college, right law school, take the right job, etc.. He had come into money shortly before he died, and based on stuff I found after he died, was working on more-or-less disinheriting me, but like many people in the family, never got around to things. He did not approve of my job, and so was going to put a will together leaving his estate to other family members. His family didn’t appreciate the result.

I guess one of the issues I feel is that I don’t exactly know the best course of action. I want to distance myself from the current situation. Just not sure whether I should just seek out a new place for myself or get her to move.

Still trying to make myself believe that there is someone out there for me. Also making myself meet people and go to social events. Struck up a conversation with a smart and educated woman this week, to me, she was drop-dead attractive. Bad thing is, she is about 13 years younger than I am. At least I am meeting people I guess.

Maybe. It is a combination of intense depression, loneliness, and anxiety. Just feel so stupid for my approach to things at times. A lot of anxiety about the future: will changes actually mean anything; does believing in a potentially better future make it more likely; etc.

Put time in on introspection, etc., over the weekend and wondering if the pain, tears, and anxiety were really worth it, especially when looking at all of the other obligations piling up at work.

Find myself asking, even professionally, will changes make a difference?

Display such an image of crassness and hostility at times that I don’t think people can see anything but that. I get lied to so often in work, etc., that I wind up being cynical to just about everybody. Also tend to be aggressive in handling things. Lots of opportunities lost with that combination.

Struggling with visualizing a better outcome so to speak. Can’t seem to get to the point of even hinting at a soft-side in a relationship. Maybe I just don’t know how at this point. Though industriousness, loyalty, and fidelity don’t seem to be that saleable.

Working on the “waking up” thing. The challenge is that my contacts collection is rather limited. Kind of like realizing that your entire outlook on things may be wrong, and you are living on a figurative island.

Kind of amazing and yet depressing to look back at things. Terrible sense of mourning. Not so much missed fiscal opportunities, but personal ones.

For about 2 decades, I have wasted lots of things with a crabby attitude, irritability, hostility, etc. Still trying to figure out why I apply the porcupine approach to just about everybody, even people I would love to have a relationship with.

I also don’t understand what triggered this what the heck is wrong with my life question, and why did it take so log to get here. Maybe stress from work, maybe it was losing somebody I truly cared for, maybe it was everything together. Would have been great if I had gotten to this point before about half my life was gone.

Gah, don’t know why as a nearly 40 year old person, have been getting hit with anxiety attacks and crushing depression between this and other things. It’s as if everything is imploding and collapsing. Embarrassing to feel like crying while at the same time feeling constantly on edge.

To Anita, we don’t really have psychotherapists out in my neck of the woods. I know, one of my jobs as a prosecutor is to do mental health paperwork, and there is basically within an appx. 120 mile radius. We are kind of primitive out here.

You are probably right. I tend to avoid situations because I don’t really trust myself to do better than how my family worked. I had moved about 2,600 miles away from home, then helped my mother out with a supposedly temporary place to live. Now, I am wondering if I should just move to a new house.

This town is pretty small. Not sure how well it would go even if I was successful in opening up. reputations tend to stick in smaller towns.

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?