I'm mostly not very good at this sort of thing. I think it's because outings and coordinating with other people to do things together make me tired, so I set my threshold for trying to make plans with someone pretty high. This is probably a bad thing. Potential solutions would be figuring out how to meet more people who I like enough to want to make the extra effort to spend time with them, or doing things with people even when it doesn't feel worth it to account for social benefits that I tend to forget about.

In what contexts do you (directed at everyone, not just OP) usually meet people? The last time I was in a new city without being in school, I attended the LW meetup group and met some friends of one of my friends through his board game club, and that was about it. I couldn't think of any others that seemed worth it. (I was both living and working an hour from the city center, which probably didn't help with people-discovery.)