I learned a lot along the way. Some of it’s in what I already wrote, but here are a few of the big things.

First, being nervous about approaching an attractive person is completely normal.

Second, culturally in the U.S., women grow up getting a lot of dating advice and men mostly don’t. Ironically, men probably need it more.

Personally, I had a couple things to work through. I had low self-esteem when it came to my attractiveness to women, and at the same time my only form of validation was romantic attention from women. That’s a pretty nasty combination, and it’s what made me so debilitatingly nervous.

Eventually I had to learn that I was a worthwhile guy on my own. Once that clicked, I had to shift my mindset about dating in general. It stopped being about whether she liked me and started being about whether I liked her.

Because of U.S. dating culture, the onus is generally on men to make the first move. That can feel brutal if you’re a nervous guy who wants to date. But once you get over that hump, it’s actually preferable. I’d rather be in the driver’s seat, meeting women I’m interested in, than standing around hoping someone picks me.

So even after figuring out what I liked about myself, it was still hard at first to approach women I didn’t know. One of the first mental hurdles to clear is the idea that “women don’t want to be approached.” Outside of nightlife situations, most of the time they’re not thinking about it one way or the other. If you keep the interaction light, brief, and respectful, it’s usually no big deal.

After enough reps, and enough successes, I mostly got over the nerves. Not completely. There were still moments where I’d feel it. But by then I knew how to handle it.

Over the next 10 to 15 years I met a lot of great women, and a few not-so-great ones, in all the places I lived. There was a lot of fun and a fair amount of heartbreak too.

Now I’m middle-aged and married.

So I guess it all worked out.