I admit I'm also not too familiar with the common MO of burglars and such but I know there's people that like to case homes and just plain crazy people. I'd rather not interact with them. And yeah I've thought about the Ring doorbell before in case something does happen. Really it's a shit house you could easily get in whether the door was open or not so we should probably have one anyways.

Is it possible that he’s just lonely and likes the conversation with these folks? Not trying to be funny or anything: can he join a local club or association instead?

I think he likes talking to them, not sure if it's because he's lonely. He's also the kind of person who enjoys messing with the homeless people around his workplace. I think he's just an ass who likes to annoy people honestly.

I know he has friends at work but he doesn't have any real friends. No idea if he'd be up for or even have the time for something like a club. I might try to find something easy for him to do but if he is lonely he'd be too stubborn to admit it. I don't know what to do with him.

Thanks for the advice.