I guess that I can derail my own thread. This got long! TL;DR – Just keep trying.
I had to give this some real thought. Talking to anyone is something that I get from my mom. If you aren’t born with the gift of gab, I get that it’ll take more effort. I tried to think of something specific and actionable. Here are some things that I came up with …
A lot of us volunteer, but I think it helps to be in a team-building role if you want your volunteerism to lead to relationships. Example: I volunteered for a politics-based organization. One of the initiatives was to write postcards. Now, obviously you could be a postcard writer, toiling alone in your home, but you likely will meet one person – the person who gives you the postcards. Try a role that puts you in contact with more people. I was the coordinator who gave out postcards to the writers and collected them. On any given day, I had contact with a dozen people. I hosted postcard parties at the office, giving people a place to congregate so they could get to know each other. I had first-time volunteers who grew their roles and are now precinct chairs! That is a huge step up in commitment, but it all started with someone making them feel included. YOU can be that person. And it helps to volunteer with an organization with a mission that motivates people and makes them feel better about themselves for doing something meaningful, which increases the chances that they will enjoy the work and keep coming and become potential friends. Another example: A friend is an editor. She volunteered to edit the newsletter for an organization. Again, worthwhile but a lonely job. She transitioned to take a board role with the organization so she sees others while still doing good for this group.
I like that @greenbutton said that this feels like dating, because it is similar. If you love running, then run with a group not just solo. And take out the damn earbuds, which says, “I don’t want to talk to you.” Many years ago I was training with a local running group for a marathon. When I traveled for work, I looked up that city’s franchise of the same running group and ran with those people. So much fun. They said no one had ever done that before and gave me one of their fancy Dri-Fit shirts and everything. A lot of running groups go out for breakfast or beers afterward. Lots of opportunities to meet people and maybe find a running buddy for a midweek jog. If you and your spouse play pickleball, great! But if you are only playing against each other then you aren’t giving yourself the opportunity to make friends.
Another idea if you are retired – Maybe when you were working it wasn’t appropriate to have office friends, but now that you aren’t working now could be the time to look up that person you always admired. I see a former boss occasionally and like her so much better now that we are both retired and she’s no longer my boss!
I keep in contact with friends I haven’t seen for years. Some of them, yes, I met through my kids’ schools and we no longer have kids in school together, but we still have kids! Ds2 especially keeps in contact with a wide range of people (hmmm, wonder where he gets it?), and I stay in contact with their moms. I wrote one recently saying how exciting it is that her ds bought a house. She was thrilled to talk about it. Isn’t that why we are here in the cafe? To still talk about our kids? lol Most of these moms have moved and don’t fulfill that everyday kind of friendship, but they are all still important to me and sometimes out of the blue I’ll hear from one and it makes me smile.
I’ve never done it, but, again, like a dating app, a lot of places have meet-up groups. I have a Zoom workout friend in Southern California, and, man, her meet-up group is ACTIVE. If you don’t like the first group, keep going until you find a group that fits.
Like dating, you have to kiss a few frogs. Keep trying and making the first move. All they can say is no, but you see how many people on this thread are in the same boat. Someone might be DYING to meet for coffee or go hear that lecture or whatever. And if they don’t, ask someone else. There are plenty of friend fish in the sea.
Story from yesterday: One of my dearest friends took me out for my birthday lunch. There was a woman sitting with a friend in the next booth who had the most gorgeous silver hair. She was kind of staring at me, too. Kinda weird. Now, I could have just admired her from afar, but when I got up to go to the bathroom as I passed I stopped and said, “I have to tell you that I love your hair. Gorgeous color and cut.” And she said, “I have to tell you I love your hat!” It was a UT volleyball cap, and we started talking about the big playoff game tomorrow night, and she said that she and her friend were going. I told her that I went to the playoffs last year but wasn’t going this year. Blah blah blah Now, if I hadn’t already had a lunch date, I probably would’ve sat down with them, that’s how well we were vibing! But it all started because I was brave enough to pay this woman a sincere compliment. And get this? Turns out a friend is giving us her tix to the game tomorrow night so I might see the awesome woman with the great hair. I’m going to make it a point to look for her. This might be my new bff. lol
All of this starts with extending yourself. Again and again. And to bring it back to the getting older theme, one of the reason why a CCRC is so attractive to me is because dh doesn’t have a lot of friends. I know that he would be so lonely in this house after I am gone so I want to set him up in an environment where he won’t just waste away alone. 
Like so many men, he relies on his spouse for socialization. So, yes, men find some friends of your own!
Our friends have died, they’ve moved to be nearer to kids, they are working and I am not, etc. etc. Throw in the whole “can’t drive in the dark” thing and I feel discouraged. Anybody else?