Yes! Magnoliy - have you read about Meyers-Briggs personality typing at all, by chance?

I relate to a lot of what you're saying. I crave deeper, more interesting conversations that go beyond people recounting the details of their lives (or their friends and families lives!)

I think that might be related to being "intuitive" (N) in Meyers-Briggs. People who are considered "intuitive" tend to focus on more abstract concepts and hypotheticals, how things will play out. Versus "sensors" (S) who are more concrete. Apparently, something like 75% of people are sensors, so they tend to be a bit more common out in the world.

I don't enjoy small talk, but have made my peace with it. For me, I've come to accept that you need it at the beginning of a relationship to start to learn about the other person, what they value and how they think. It gives you a way to start to get to know someone without accidentally hitting on volatile topics that might turn ugly quickly.

I don't know how to find more people to have interesting conversations with though. And, I'm finding that (as an introvert) I tend to suck at actually initiating these conversations... I'm trying to be better at it, but I guess when most people don't share your interests, the chances that someone is going to respond positively when you toss out a conversational hook is low.

What I've found confusing is that, even people who seem to be interested and curious about things, sometimes seem to be terrible conversational partners. I have a friend who is interested in philosophy and making an effort to read some dense philosophical books... how cool, right! So I asked him, the book that he's reading, has there been anything really surprising to him? Anything new he learned, or that he thinks about differently now? What's his biggest takeaway from the book?

Good questions, I thought. Good opportunity to talk about what you're reading.

He told me... "Well, I don't understand most of it, so I'm not sure. I just want to be able to say that I read it, because I think that's cool."

How do you respond to that? It's hard for me to imagine reading something just to impress people, how do you even work that into conversations if you can't talk about the content?!?

Sigh. So, no answers here... but I can relate!