I'm going to wade in here uninvited and try to share what I've learned about how to talk to other humans. A lot of the above is vague. I so, so get it. Discomfort, "having a bad time," socializing as a concept, small talk, hurdles, uncertainty, isolation, unwant, connection. These are sweeping concepts to address and summarize how you are feeling about your social standing, your worth, all those big things.
Big things are only the result of a summary of a bunch of small things. If you don't have actual moments of being in a space with other people and even trying to talk to them, you cannot summarize what you are like with other people in that space. You can't do math on zero. You shouldn't do math on a low sample size either. (Yes, I know you CAN. But this is about trying to figure out how to do better, I think?)
So I'm going to try to say things that are SPECIFIC. "Fake it til you make it," is FINE, but WHAT are we faking?
I was going to order this in steps but that felt silly. I have no idea how I acquired these behaviors or in what order. Also Tumblr is actively removing my ability to move text around. So!
Let go of "good time" vs. "bad time." It's just time.
Don't duck and cower. If you are in a public space and want to, project a mild interest in folks by not mimicking an armadillo.
Remember that interest doesn't mean you have to say yes to anything, ever. But say yes when you are invited and your only hesitation is, "wait, me?"
If you're not going where people can be in proximity to you and speak to you, you aren't doing anything in this direction. You can have so many reasons for why this is hard. But. Talking to strangers requires strangers. I'll be your stranger if you want me to (I'm AWFUL at internet connection and great at everything else, maybe you will all put me through the ringer).
Let go of specific, "I want to make a friend who is this type of person who blah blah." If you go out once, and you don't, you won't. If you go out twenty times, you maybe will, and if you don't, you'll have twenty times you've bolstered your people observation skills and met other people.
Ok, the specifics. Get close enough to someone that they know where you are and wait for them to orient toward you. Say a little hi. When they know you're there, ask an open ended questions. "What brings you here?"
If someone set up space for you, it's for you. Imagine someone saying "sorry" and "is this ok?" one zillion times in the space you set up for them vs. "oh thank you so how does this work I like what you did with X" who do you like more?
Crush the shame until it can't crush back.
Fuck, just put the fun back in. My friends and I in high school talked about "good people watching" and sought out situations for that. You're not a little lamb, you're a big primate watching other primates. Be open to the weirdness.
"Go out" is an inclusive act that means chatting to anyone. I learned a lot from chatting up nurses and facilities guys at my college.
Pick ephemeral situations as testing grounds. Standing in line for coffee, groceries, whatever. Waiting for a bus. Sitting down or slipping out of class.
For longer attempts, pick open social situations like clubs, sit down coffee shops, the cafe, libraries, bars. Subjective which is why:
Figure out: What the heck is happening in this space? Are people in little groups? How are they greeting each other? How is a new person welcomed? To be clear, break from standard if needed. If everyone is sitting and reading, and you want a coffee, go get a coffee. Don't assume your tiny snapshot is enough to understand everything.
If someone is being social in way you like, watch and learn and do.
My dad used to wait humbly as other folks would move through a (museum, restaurant, historic area) before he'd greet them. Then he'd ask questions: "how did you get into this? do you have a favorite thing? I liked to see this, what are your thoughts on it?" Be kind to folks.
Be curious about people. Let your interest in the other person, their tapping fingers or slow conversation or good outfit shine through. Loving others lets you love yourself