Counting Regrets

From Zanecorpwiki

I have a particular conceit wherein I would recount to myself all my regrets in life. I'm not talking about missing questions on a test or being late for this or that. Those are little things.

Regret does not come from losing. Losing is something that can happen for all sorts of reason. We're constantly losing.^{[notes 1]} So much of an outcome is if not blind chance, then something which from our perspective looks very like it. Sometimes those odds are so against us, that losing is assured and discretion being the better part of valor, we step away without regret.

Regret occurs when we had a reasonable chance of success^{[notes 2]} but failed to try.

All this is important to understand because it's easy to think that these regrets are somehow my greatest losses. In the end, only two of my regrets really trouble me, and I consider neither of those my greatest loss.^{[notes 3]} Yet it's the regrets I focus on because regardless of the severity of the outcome, it's the regrets which really should have gone better.

They are:

Failing to ask out a certain girl in high school': I was a late bloomer and came to dating without much prep work. I had friends who dated, but did not see them in the mode enough to really absorb any of it. No older siblings, and was somewhat isolated.^{[notes 4]}

I did ask girls out, but it was hard. Not only did I have the normal problems of raging hormones and adolescent paranoia-bi-polar-crazy to deal with, but I had no practice. My technique and understanding of things was immature and naive to the point of being almost alien. I'd constructed a very literate, classically romantic view of love that included among other things fierce chastity and self sacrifice. Combine this with the adolescent mopes^{[notes 5]} and you get an surreal caricature of high medieval chivalry and angst pop.

Which is all to make the fairly obvious point that when I failed in "making a connection" I took it very hard. That in-and-of-itself is not unique, I'm just describing the character of my reaction. It became a sort of existential crisis. The rejection became a reflection on my ability to love, for love is grand and pure, and is itself not rejected. Therefore, the nature of the love I held was itself imperfect. That love, being a reflection of myself, therefore meant that myself, my soul, was flawed.

Of course, in reality, this was all nonsense. It was a bunch of awkward kids trying things out. It was important, and these things do mean a lot, but not in the way I thought at the time.^{[notes 6]}

The point being that I'd been trying to date, but it just wore me out. Then I really fell for this girl who I know--and honestly knew then--would have been receptive. At that very moment, though, I fell to the temptation of self-doubt. When she started going out with someone else and I couldn't tell myself, "I'll ask her out tomorrow."^{[notes 7]} there was a sense of regret that was very different from all my other failures.

I used to list others that I'd regretted not asking out, and there are a couple that there is some small regret over. A couple, there was just bad timing in one sense or another. One or two I probably should have gone out with, but would have broken up with after a few months and kinda felt that was the case.^{[notes 8]}

Losing some Star Trek stuff:^{[notes 9]} In late 2006, I was trying to get rid of all the Star Trek stuff I'd collected when I was younger. I'd finally realized that it was the act of collecting, and the memories of the times I spent with a very good friend of mine who would later die quite young, that I cherished. There were a few items I really did get enjoyment out of^{[notes 10]}

Anyway, I'd gathered everything I was going to give away together, taken pictures, and posted to Craigslist. I didn't have anything great, but I really wanted to find someone that could appreciate it all. Problem was when they came over to pick the stuff up, there were a few items I couldn't find. Turns out they were the items they really wanted. I lose things a lot, but I honestly don't lose things that I really, really take the time to care for. In fact, I take an almost curatorial stance towards those things I invest special meaning in.

It may sound like a silly thing, but losing those items, and disappointing the couple that had come to take stewardship of my collection (as it was) really stuck with me. I kept the email in my inbox for years afterwards and spent whole weekends rummaging the garage trying to find where'd I'd mislaid the items.

Being suckered by the duct cleaners:

Notes

1. ↑ One could consider anything but "optimum" is a minor loss, even if still "successful"
2. ↑ Reasonable being defined not by any absolute percentage, but relative to the weighted gain loss utility.
3. ↑ I would say in terms of loss, they are both in the middle of my top 10.
4. ↑ I used to consider myself introverted, but looking back I think it was more that I different. I found myself very entertaining and just had a different... way of engaging with others. My point being, I never felt antisocial and it wasn't like I didn't have friends or was not liked, but I spent a lot of time by myself and not as much time engaging in social interaction as one would expect for my age.
5. ↑ Not that I considered myself particularly mopey, but this goes back to the bi-polar thing. There's that really clear adolescent mopiness that is such a part of the experience.
6. ↑ I say this, but even now I don't think I was wrong to think the way I did. In other words, I believe even now that had I been firm in my affections--rather than by turns forceful then bashful, now sure, now confused--I would have met with a positive affection. It was primarily a question of technique rather than intent and therefore a judgment, yes, but of my experience rather than my worth.
7. ↑ I have a specific--though admittedly vague--memory of a certain stretch of time where I vowed to myself every morning, "Today will be the day I ask her out." Then I'd find some excuse, and fall asleep with the thought, "Tomorrow it must be."
8. ↑ Looking back, I think it was silly to not have had some fun dating at that stage in my life when I really had nothing else to do and dating was crizazy.
9. ↑ This is actually the reason I'm writing all this down. So I can finally let go of my regret and archive away this email I've had in my inbox for 3 and half years.
10. ↑ My collection of the early books, some utilitarian glasses, and a signed copy of a comic written by my favorite actor, George Takei.