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Notes -
How did you meet? How have your expectations for a partner changed over the years and across relationships? Do you have any regrets that you learned from or might be generalizable?
She started a Meetup.com group dedicated to following the local baseball team. I went to the first meeting, and she and I got along right away. We started talking outside the Meetups, and after a few weeks I asked her if she wanted to go to the baseball team's Hall of Fame with me. From there we just kept doing stuff together; when I "asked her out" it wasn't really a big transition in our lifestyle by that point.
Let me share something which is kind of embarrassing now, but to which I bet many men can relate. When I was in my teens and early 20s, I actually described my dating behavior to my male friends as a "quest to gain XP." That is to say: the only criteria I set in those days was 1.) looks okay 2.) is willing to date me. This is a daft way of living your life, to be honest. I certainly did date many kinds of women: a schoolteacher, a college professor, a pediatrician, a hairdresser, etc., etc.
In hindsight, I know that I was just doing this for validation. I was a very ugly, awkward kid until I finished puberty, and it took me an extremely long time to develop inner confidence. As a result, I was dating without actually assessing my partners for any kind of suitability for long-term relationships. I just wanted physical affection, and to be continually told I great I was. I did get those things, and unsurprisingly, it did not make my life any better, and left me wondering what the point of it all was. Meanwhile, I created all kinds of false expectations in my girlfriends, which would inevitably be disappointed after I had wasted much of their time.
It was in 2020 that I had this realization fully, and at that time I stopped dating entirely; I realized that I needed to make a decision about what I was trying to accomplish, and to stop causing unnecessary pain to other people. So I concluded that I did want to get married, I did want to start a family, and that I needed to focus on cultivating the characteristics in myself that would lead to success in these endeavors, and to find a partner who had them as well: emotional stability, the capacity to love strongly, honesty, high time preference, and so on.
I repent greatly of the way I handled dating in the past. It simply added to the amount of misery in the world. I wish I had known better.
“Strategy without tactics is the slowest route to victory. Tactics without strategy is the noise before defeat.” - Sun Tzu In the past I learned tactics about dating - about how to be charming, about how to make people like you, etc. I had no strategy: I had no goal, and so there was no way the relationships could go anywhere. It feels like a big waste of time, and while one might say, "You learned something and so it wasn't time wasted," I am cognizant of the fact that by being married at 35 instead of 25, it's 10 less years I can enjoy married life.
If I had had a plan to begin with - I did date some excellent women with whom I might have built excellent lives. Those opportunities are now gone. I love my fiancée, but people should be aware of the "secretary problem." https://en.wikipedia.org/wiki/Secretary_problem
It's fine to date for fun. I don't have an issue with doing that. I would recommend anyone who is young, though, to start thinking about the big picture of their life as soon as they can conceive of it. I do, honestly, wish I had done that.
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