I have similar issues with maintaining friendships. I used to go out of my way to make/keep friends, but unfortunately that always leads to them responding the same way the ppl are with you. I've heard that it's a system of "social value" that is off kilter. That mixed with the failing of the family unit has left most ppl with really sorry social skills. In my country, our basic social structure is based on competition and hierarchies that trains most ppl to either be submissive or dominant with no real in between. Thats great if you're trying to climb a treacherous corporate ladder, but leaves a lot to be desired where friendship is concerned.
Getting older definitely does not open a door for keeping friends or making new ones. Ppl get married, have kids, focus on careers. You will find ppl you can talk to at work. I totally don't suggest the military unless your hearts in it. Once you're in, if you don't like the view...too bad you're stuck there. They say the friends you make in college are the friends you have for life. That's bullshit too. I joined a social fraternity in college. Met a bunch of ppl, drank a SHITLOAD OF BEER, got in a little trouble and had some fun. Nothing I wanted to maintain once I was out of school though.
You sound like a smart guy. The fact that you're questioning the value of your relationships shows it. Focusing on yourself will build your confidence and help you be at peace with yourself, that can really attract ppl. If you're happy with yourself, ppl can tell and they want to be around that. I can't tell you how to do that though. I'm thinking about joining the Freemasons personally. I'm hoping to find some honest ppl so at least I know who I'm dealing with, and at the end of the day I can feel good about myself for helping children.
Not having a steady income can hamper meeting new ppl too. I can't think of a single thing to do in my town without money, besides going to the park. That's probably not an accident, but I'm not going to get conspiracy theory about that shit. You might try learning a musical instrument. There is a lot of satisfaction in it, the world needs more musicians, and it's a good way to meet good ppl who might not judge you based on what you look like or get "nerdier than thou".
I'm dragging the Bombcast lake for interesting episodes, and I'm curious if you all have some suggestions or stories about good shows to revisit. I'm a fan of the GB origin story, a la Arrow Pointing Down, and can def suggest that for neophytes. If you like that, you might also check out the "How To Build A Bomb" series on the YouTube channel.
Also, I sometimes play dubstep in the background of the podcast.