I'm not sure if I'm alone here but I just lack social skills. It's like everyone but me has this secret book of how to interact with people. I'm not autistic or anything but I had little social life when growing up. I was actually rather popular at the Internet but that didn't translate well to real life. I'm now trying to catch up in my early twenties. I meet interesting people every day but connecting with them non-superficially is the hardest part. I am too shy to talk about anything and I have low self-esteem. I literally start to mumble when telling a story if I don't know the person well. So far rationalizing about it hasn't helped.
This is something I see pretty often. I'm a business co-founder, so this stuff is pretty much my bread and butter.
An idea I've been kicking around is some kind of "Social Skills Primer" type product, probably done by video for ease of explanation and to capture/explain nuance.
I haven't fully decided on doing this yet, but would that be interesting to you, do you think?
As a side note, I would highly recommend reading How to Win Friends and Influence People.
If somebody said to me what you just posted, I would want to talk to them. I feel the same way. It's often jokingly pointed out that two introverts will never engage each other. I think that in addition to being funny, it's also true.
It's a wonder I managed to get a few friends.