I think he probably had some wishful thinking and incorrectly assumed things.

I think you are very trusting and a bit too nice. It’s ok to meet new people or reconnect with old ones but give it some time to develop into friendships or anything else. Don’t overshare right away or hang out excessively. I am in my 50s too and if I ran into college classmate I’d not be telling him about having legal fees or any other kind of personal troubles. He has zero needs to know. Why’s he privy of all this. Some jerks do prey on vulnerable women and want to be saviors. You meet him and right away he finds out you are having all kind of issues. He jumps on his white horse assuming things. Some men incorrectly assume that women share their troubles because they want men to fix it. Is it your fault he’s an idiot? No. But protect your heart and soul. Don’t jump all in into these entanglements

As about texting him. I am known to be paranoid about people not replying because I imagine horrible scenarios and sadly it’s known to happen. But that’s in case of my elderly dad. Or my husband. Or my daughter. I even get it becoming irritated with someone I am old friends with who doesn’t reply. But not some dude you went to college many years ago and nor run into in the bar. Who cares if he didn’t reply in the morning. I’d not be texting him more than once.

I’d not stop going to venues you like. Just don’t sit by him. And I don’t think it matters where you meet people. You can meet a serial killer in a church and a nice guy in a bar. There are no rules. But generally speaking bar scene might not be the best place to meet people for serious deep connection. It sounds like these are bars with live music rather than actual concert venues. Again not wrong. Just be more discerning who you meet there and who become your friends or dates.

Also substance abuse and bars go hand to hand. People you meet there might be a bit boozers and stoners so their judgement is likely off. I doubt they go there to drink tea and hot chocolate and enjoy sober company and have a conversation with substance. I might be wrong of course but I doubt it

Glad you done with the guy. Keep being careful who you associate with