He's not really tried to date though.

He's on dating apps, which are for hook ups, not people looking for a meaningful relationship. He goes to bars and stares at the counter. He goes on walks in parks and stands around looking surly.

That's not trying.

That's going to the barber shop when you need to get your tires rotated. Do you get what I'm saying? My grandma used to say, "don't look for deer at the bottom of a lake; you won't find anything but catfish". You have to appreciate the irony there as she was saying that well before "catfishing" was a thing on the internet and in the dating world; also well before dating apps came along and made emotional romantic manipulation so much easier to pull off.

But he won't disengage from those damned dating apps even while acknowledging that they're messing with his head. He won't do anything out in the real world or build real social skills. He's built a reclusive life and is now sad that it was so successfully built and now he's lonely.

But you're right. He's a decent enough looking guy. He's articulate. He has interests. Even if he is painfully shy or what have you, it's not like there's not plenty of women attracted to those types. Can't promise the relationship would last, but there would be one if he wanted it.

But you have to cross paths with them and you won't do that hiding out.

Then there's the fact that he's not finding any of the women acceptable. He plays it off as this, that, or the other....but in all his articles and commentary on Medium, he's not extending invitations and then blaming women for not being interested or that he's confused what women want because if he approaches them he'll be labeled as creepy, or whatever.