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.)
As in, how do you find ways to meet the right people you talk to? Presumably, they would have personality fit with you, and be high on both intelligence and openness. Furthermore, they would be in the point of their life where they are willing to spend time with you (although sometimes you can learn a lot from people simply by friending them on Facebook and just observing their feeds from time to time).
Historically, I've made myself extremely stalkable on the Internet. In retrospect, I believe that this "decision" is on the order of one of the very best decisions I've ever made in my life, and has made me better at social discovery than most people I know, despite my dual social anxiety and Asperger's. In fact, if a more extroverted non-Aspie could do the same thing, I think they could do WONDERS with developing an online profile.
I've also realized more that social discovery is often more rewarding when done with teenagers. You can do so much to impact teenagers, and they often tend to be a lot more open to your ideas/musings (just as long as you're responsible).
But I've wondered - how else have you done it? Especially in real life? What are some other questions you ask with respect to social discovery? I tend to avoid real life for social discovery simply because it's extremely hit-and-miss, but I've discovered (from Richard Florida's books) that the Internet often strengthens real-life interaction because it makes it so much easier to discover other people in real life (and then it's in real life when you can really get to know people).