Hi Dan! I don't really have advice to offer but I have more or less been in your position so feel compelled to reply. I will try to keep this as brief as I can. Also, I'm not trying to be braggy...I just want you to know if there was hope for me, there's hope for anyone.
I've always been the shy, introverted type. My self-esteem isn't the greatest and I have body image issues. My teen years were shaped by family tragedies so dating just didn't happen - I was struggling just to hold it together. During that time I found I was more comfortable with online friendships/relationships than the real thing. After high school, I went on to earn two degrees and was pretty busy/focused on academics.
When I was in school, I took for granted how easy it was to make connections. I didn't socialize nearly enough because I assumed those opportunities would always be there. Then when I got out into the workforce I realized how hard it can be to meet people. That was especially true because I was working in a small town with no co-workers my own age and noplace to really meet anyone like-minded.
Over the years I did try online dating a couple times - at ages 25 and 27, I think. Nothing ever went anywhere and I took each rejection very personally. It wasn't a good experience considering I already had pretty fragile self esteem. Eventually I decided I couldn't handle it and gave up. I kept hoping the "love comes along when you stop looking" thing was true...but in my case, it wasn't.
At age 29 I was a virgin who had never even been kissed or had a real boyfriend. I felt like a freak. I thought there was something wrong with me and no one would ever want me.
By 29, I had made some pretty significant changes in my life. I'd quit my stressful job, found a new career path and taken steps to regain my (emotional and physical) health. But I still had no idea how to meet people my age who were at the same stage in life as me. I decided a small town just wasn't the right fit for me.
I decided to take a vacation to the city I thought I'd like to move to. I found a vacation rental and joined OKCupid a couple months before I was due to arrive. I "screened" a ton of guys and went from feeling very hopeful to very depressed. I'm sure the female OKCupid experience is different from a male's, but I ran into a lot of creeps, liars, fakes and guys who just weren't the right fit.
I briefly contemplated whether I needed to broaden my search parameters. There were very specific things I knew I wanted in a partner, and I really wasn't interested in dating for the sake of dating...I wanted something with longterm potential and didn't want to waste my time on incompatible guys.
I began my vacation with no dates lined up and felt completely disillusioned about the whole thing.
After contemplating deleting my account all together, a bottle of wine and I went on a "liking" spree. Before I had been extremely selective. This time I clicked the "like" button much more liberally - they were still guys I thought may be promising, but I wasn't sure.
The next day I logged on to a nice, thoughtful message from a guy who had seen I'd "liked" his profile. His profile, by the way, was unremarkable in every way which was why he'd never really stood out to me. His photos also weren't the most flattering.
We sent a couple messages and then he suggested meeting up. I figured what the hell, so agreed. We meet up the next night. I went into it with low expectations but he turned out to be better looking than his pictures had led me to believe and, even more importantly, he was incredibly sweet. Our coffee date lasted over five hours and turned into a dinner date.
We've been in a relationship for a while now. We're long distance for the time being but I'm going to be moving soon. I've gotten all those "firsts" out of the way and you know what? I was placing WAY too much importance on the things I'd never done - especially losing my virginity. I built it up to be this big monumental thing and felt a lot of anxiety about it. In retrospect I think that was silly of me.
As an aside, it turned out my boyfriend was a late bloomer too. He's a sweet, shy, nerdy guy in his 30s and I was his first kiss and everything. I can honestly say I wasn't the least bit bothered by it...actually I liked that we got to experience things for the first time (and be awkward) together.
Dating aside, friendships have come easier to me lately. My boyfriend isn't quite as introverted as me, so my social circle has expanded through him. I've also reconnected with a couple old school friends in that city as I think it's important to have my own life independent of my boyfriend. (I reconnected by simply being more active on Facebook, initiating conversations and then inviting them to hang out and catch up.) I expect I'll eventually befriend some of the people they introduce me to. For an introvert like me that's more than enough.
I feel for you Dan, because I've been there. I've felt really lonely and like no one would ever want me. I've struggled with depression and physical health issues that left me drained. I've wondered why everyone but me seemed to be able to find a partner and if something was horribly wrong with me. The longer I was alone the more broken and undesirable I felt.
I realize now that for many years, I wasn't putting myself out there because I was scared of getting hurt. I didn't know how to flirt or pick up on signals or meet new people. And even after I tried to make more of an effort, my attempts fell flat for a while. Sometimes I think it just comes down to timing...but being open to somebody coming along and keeping an eye out for them is essential, I'd say. And if dating doesn't go as you'd like it to, think of it as practice.
Lastly, I just want to commend you for all the work you've done. People gave you advice and you've taken it to heart. I'm sorry your efforts haven't been more fruitful but don't give up! It just takes meeting one person. Once you're feeling up to it, change your approach slightly (different Meetup group, completely new OKCupid profile, new hobby, new local hangouts) and try again. Does your city have a subreddit you could be active on?
I guarantee you there are people out there looking for friends. There are people who would love to join you at the events you mentioned going to alone - it's just a matter of finding them. Same goes for dating. If you'd ever like me to look at your OKCupid profile for you, I'd be more than happy to offer any advice I can. I know the people in that subreddit can be harsh sometimes, but I promise to be honest in as nice a way as possible.
Good luck!