Very fair, and worth addressing. May I ask- what are the main barriers preventing you from socializing? Could intentionally designed apps or social structures reduce those barriers? What do you think would be most helpful?

1. I would go out alone to some events, but most of the time I would end up not speaking to anyone because people were not approachable. Everyone else is typically in groups and closed off to outside interactions. There were some exceptions but that was the norm.

2. I'd search for some hobby/interest groups that would fit my interests, but nothing really fits. Either there are no meetups for such interests or there are meetups but the demographic at those meetup is not the demographic that I am interested in meeting.

3. Out of desperation I tried to be open minded and joined some hobby groups and did some sports that were really out of character for me. Here I did meet some interesting people, but I did not make a good impression because I was so obviously out of place.

4. Eventually my Friday nights consisted of going for a swim at 21:00-22:00 or going to the library of the nearest university so that I could feel some kind of social warmth sitting in a hall with all the other people.

1. I think you would be surprised how much people are friendly in a socializing event if you just showed up and said hey I'm new, can I join in this conversation. Then just listen 80% of the time and maybe ask a question or two. Then do it again with a follow up of what you listened to. Just keep at it.

2. What are your interests, precisely? And what do you mean the demographic you are interested in meeting-- what is that demographic, precisely?

I feel like these things really compound on top of each other. It’s so much easier to go to these kinds of things and meet people when you have a group of likeminded friends to go with.

>2. I'd search for some hobby/interest groups that would fit my interests, but nothing really fits.

You can just start your own group in this case. That's what I did with Lisp Ireland.

That is not "just" for people who do not have social skills, do not know how to fit in etc. Starting something is a thing people with good social skills and confidence do. If you already feel rejected and do not know how to make interactions work, trying to start something will make you feel even more rejected and lonely.

I believe you’re overestimating my social skills and confidence. I created an event on a meetup site and people showed up.

I can relate with point number 2 about demographics. I've been involved in organizing and playing at local raves and parties since forever but this year I stopped completely because as I age I don't share that much with the people there. Being in my late 40s while everyone has 20 (or even less !) sucks. Some people will give me the look that I'm out of place and others will just share concerns of their age that are too far from mine. This and the booze/drug thing that is frankly not compatible with an aging body and a dad's responsibilities. So that's it, no more friday nights for me, I'm better off at home. I'm not sad though, change is good and I started shooting a few years ago and the range is now my new meet up. Kids are welcome, so I can both socialize and spend time with them and have fun, it's great.

I'm sure there are other hobbies that would suit you.

Age is a big one. But also for me it was a realization that I have different needs and the people I'd meet through my interest in some nerdy hobby were not going to fulfill all of my social needs.

Where do you live? I'd love to go grab a beer with you.

Thanks for the offer, currently I'm road tripping around southern Europe, partly as a way to escape from all that.

"people were not approachable"

frankly this is just a bad mindset and not a true description of reality.

For many people, it's probably no deeper than the question, "where would I go?".

Depression, avoidance, not finding yourself fitting in etc, old friends all live somewhere far away