In the spirit of the loneliness thread in this conversation and making new friends at an older age, it was one of my goals when I retired, and I've been successful so far. I have learned several things from doing so.

First, if we haven't done it in years, it feels really scary. I'm not sure why that is, but I'm guessing it is because other people will judge you and decide they don't like you, and if that happens, too many of us assume it's because there is something wrong with us. It takes getting into a head space where you don't want to be liked by everyone; it's fine to not click with other people and when it happens, you'll just move on; and it's a long game -- you're not going to make 5 new friends right now, you'll make 5 new friends over the next two or three years by taking advantage of opportunities. I didn't get there by being this organized, of course -- I got there by trial and error. I decided to try something, anything, to deal with my fear and intimidation and shyness, and gradually figured out how to pull it off more regularly. (Your mileage may vary, of course.)

Second, there are ways to make it less scary. In my case, as an introvert who does not enjoy group settings, I've settled on just suggesting to people who seem compatible that we get together for coffee. Sometimes they say yes, sometimes they say no, sometimes they have no idea how to respond because this isn't something that happens when you are a librarian speaking with a library user. But really, all of these consequences are entirely survivable. I recently started getting together with someone I connected to on my Buy Nothing group on Facebook. You mostly just need to put yourself into situations where you get to naturally chat with other people for a while. And realize that most of those chats will go nowhere in particular, and can still be enjoyable for a few minutes.

Third, I go into those first coffees with the expectation that I'll enjoy the one-on-one conversation, and the first one may be the last one, and that's OK. Each time, I learn something about how to do it better the next time. Also, just because the person may click with me doesn't mean that I click with them as we get to know one another, which is a judgment-free conclusion.

Fourth, if I get a rejection off the bat, or suggest a follow-up and get a sequence of "not nows", I take that as "no" and move on. Ditto if I'm ghosted. Again, it just means we didn't click, not that either of us is a bad person. It also means that most of us don't have a good way to say "it's not working for me" or "my life is too full already" or "what the heck -- who does this?", so we use awkward ways to signal that.