We've been friends since middle school, and there were many years when we weren't in touch. (We're in our early 40s now.) Yet he never totally went away, and has always managed to track me down. Not in a creepy way, but in a "I want to keep in touch" kind of way.
So there are two weird things going on. 1) I can never be myself around him, because the more "me" I am, the more uncomfortable he gets. Like, he visibly withdraws. And there's only been one occasion that I felt like we actually had a real, true conversation that went beyond the surface. That's one conversation in 30 years. He's one of the most surface people I know, but nonetheless, he is a connection to my childhood and I've generally been happy to see him occasionally. As long as I stick to the surface, he's fun.
2) He only ever wants to see me in group situations. Friday night, he invited me to join him for the Bears game tonight. I said "Great! I'd love to. Send me the deets and if I'm not working, I'll come." I heard nothing from him. So I texted him to if plans were still on for the game tonight, and this is what I got.
I had to pull the details out of him, text by text. It was really strange, considering his enthusiastic invitation 3 days ago. I suspect that the dude who was organizing it gave him an earful because we don't get along. Which, you know, fine. I was disappointed, because I was looking forward to a fun night, but if I had known it this guy's gathering, (and a hometown gathering to boot) I never would have said "yes." So I decided I was "working" and stayed home. (Which was the right choice. Great workout and excellent dinner. But I digress.)
Anyways, this is the kind of weird, passive-aggressive bullshit he's always pulled. I've never cared about being part of any group associated with people from my hometown, because a lot of them are jerks, and most of the others I don't relate to, because of totally different life-paths. (I like a few—I'm not a misanthrope.) These events are usually awkward, (and have been since we were 19) but for some reason he wants to include me, and won’t get in touch socially in any other way. He either doesn't really like me, but holds on because he's a guy who values long-term connections (which I know is true,) and uses these events to satisfy his need to stay in touch, or he's never gotten over his high school crush and it's too weird to hang out one-on-one (unlikely, but possible, I suppose?) Either way, I think it's very likely I'm never going to see him again, and I'm super ok with that. I don't have time for people who can't be real.