Have something meaningful that's on your mind, and periodically share it while being polite. As long as you're polite, it's rather unlikely that any attention/interaction is unwanted- partly because so many other people are lonely and starved of meaningful interactions too.

Maybe you have a note on your phone or in your pocket of what's been on your mind. Maybe you notice something in the moment. As long as people aren't upset or in a hurry, they tend to appreciate someone talking to them and trying to find common ground. Going to events is a really good way to increase the opportunities for doing this.

Much of the time, any "awkwardness" that's there is a creation of your own mind. It takes a bit of experience to get used to convincing yourself "there is no reason for this to be awkward, I'm just being the genuine version of myself". There is no external script that you might be failing to follow. Just follow you. Not everyone will click well but some people will, and they'll make it all worth it.

At 19 I was a shut-in with no in-person friends and didn't really know how to talk to people. These days it seems like half the town (even after the location changing a few times) knows me. And I'm extremely eccentric, and somewhat introverted.

You're doing it right now player, what's up

A constant revolving door of hermitude, trying to build a social circle, then finding out that for all of their "you can be yourself, you don't need to mask around me", turns out I do have to mask around them; and then I leave again.

Find fellow neurodivergent people with similar interests to chat with. Or my favorite, get collected by an ADHD person and then meet people that way.

I go through long stretches of self isolation and have emerged back into the world successfully multiple times. I'm currently back in hermit mode and needing to get my shit together so I can get my life moving forward productively again, so I might be able to relate. But I don't want to go rambling on an unhelpful tangent.

Are you asking for direct practical advice, commiseration or just other people's experiences / strategies for socialising-while-awkward?

Mutual interests are the best way! You can skip past awkward small talk and just chat about something you’re both interested in. There are loads of social hobbies that are great ways to meet people, just pick one that you’re interested in and try to find a local group for it. I’ve met some great people from board game meetups, running groups, scuba diving, protests, you name it.

It’s also incredibly easy to make friends with other expats if you’re traveling in other countries, they’re usually also lonely and directionless so they’re much more open to hanging out with randos. Staying in a hostel is pretty much a guaranteed way to meet some cool people! Locals are also more forgiving if you’re a little “eccentric” since there isn’t the same expectation of following all the unspoken social norms that some ND people can struggle with. Obviously don’t be an obnoxious tourist with no respect for local customs but like, you have some extra wiggle room in interpersonal interactions. I know travel is a very privileged thing but I highly recommend it if you’re able to.

Last year I was incredibly depressed with literally one friend and almost never left the house. I’m now a bona fide social butterfly making new friends every time I go out, you CAN make that change. It’s a matter of getting out there and putting yourself in situations where you can meet people. It does take courage and a willingness to be open and vulnerable to others, just taking that first step can be scary. However, I’ve realized that people are way less judgmental and cliquey than I previously thought. If you approach people with genuine respect and sincerity they’re not going to give a fuck about all the silly little things you’re insecure about and will usually reciprocate that same respect.

My own advice is to join an organization, volunteer program, club or class, and to go to free events in your local area^[This footnote is a bit late but please be aware of mitigating COVID.]. At least speaking for myself, the problem with social interaction is mainly just the unpredictability, right? So the best "hook" to build social skills from is going to be the more predictable social interactions, or at least the social interactions that "feel" more predictable and less risky. This can be something like a support group for your form of neurodivergence, sure, but it can also be a wide range of other things. Lately I've liked talking to old ladies, for instance. If you're struggling even talking to cashiers, librarians, and train conductors, then you start there.

Some other things to note is:

1. There's talk sometimes of asocial people getting "adopted" by someone who's very talkative and extroverted, but the fact of the matter is that you can yourself be the adopter. You are not the most asocial person in the world, there's going to be times when you aren't even the most asocial person in the room. And in those times, you can be as weird as you want to that person, because what exactly is that person going to do?
2. You can "fake" confidence to some extent. Being an overseas American has actually been kind of helpful to this end because I can play into the rootin tootin yeehaw stereotypes/clichés, and play into the ways I already end up standing out — although that is also obviously something you have to be a bit careful with. But yeah, picture yourself in the third person as someone more confident and try to act as that person would. Fling the door open like Cosmo gotdang Kramer and say something silly. Do a silly voice. No-one's going to stop you, and eventually the "fake" confidence just becomes actual confidence.

Ganbare biimu!

For me it started to ease when I started drinking, but I can hardly recommend that

Are there any art or maker groups in your area? If you can get to one (or more) of those, there are going to be people who will fall over themselves to talk to you if you just ask them about what they've made.

People love when someone shows an interest. You don't need to know anything (or pretend to know anything) beforehand, and the same few questions/prompts can be reused: from a vague "tell me about [the thing you made], to "what was the hardest part?", "how did you do this bit?", "did you learn anything cool along the way?", "what do you think you'll make next?" So long as your interest is genuine and you actually listen to what they say, you can't really mess things up.

And if you want to make anything yourself, regardless of your current abilities, such groups tend to be quite nurturing, where someone will show an interest in you too. Art in particular is an expressive pursuit that attracts lefty weirdos. The desire to connect with people is right there for you to be a part of.

With my mouth

I can talk to people, but it often feels fake to me. I don't have a coherent sense of self, let alone the social awareness to package myself to others in a way that is both authentic and lands well, so it's hard to be real with people. And, consequently, it's hard for me to form strong, lasting ties to other people. Music is basically the only medium in which I feel like a person.

I can talk ok but I do not know how to approach someone, acknowledge them without being first acknowledged, or build relationships let alone looking most people in the eye without getting pretty anxious. Even when I’m lucky not to initiate I’ve only felt “connected” to people for very brief moments.

I was going to dump a whole bunch of superfluous information for some reason, but the useful thing I had to say was this:

You won't meet people by being alone. Go somewhere with people, preferably many, and find the most extroverted person you can. That kind of person is usually willing to do a lot of the conversational work for you if you can mention even a token topic, and furthermore extroverted people tend to have a lot of friends, so you can benefit from having a bunch of people be easier to talk to because you've got the extrovert fellow vouching for you and perhaps also participating in the conversation.

As a more literal response to your question, it can be easier to hold a conversation in a group. Yeah, for people like me and possibly you, the prospect of being in a group is kind of intimidating, but the great thing about groups is you can be silent for much longer stretches of time without it being any problem, and then re-enter active conversation at a point in it where you feel most comfortable.

Reluctantly

preferably without spreading covid or a novel bird flu mutation

the sorts of people attending group things are unlikely to be comrades, idk what all this 2019-ass advice is.