Your brain, like mine, might have trouble handling social interaction by default, but if you devote sufficient attention, you may well make progress, perhaps even significant progress. In my experience, many nerdy people who claim to have trouble understanding people don't direct anywhere near as much cognition towards social interaction as they do towards the things they are good at

The last part is certainly true but I'm not sure I don't enjoy socializing by default: when I was a kid I never lacked for friends and was pretty open and curious about them but growing up has changed me. By age 13 I felt I had too many friends, so I was not able to give each the attention they deserved. Not that I cared about them deeply. My family moved to a different home every ~5 years and I went to 3 different schools and I didn't stay in touch with my old friends for more than a year or two after moving. I've mostly had "situational" friendships. Now, at age 27, an hour or two of social interaction/week seems enough.

You get a certain emotion when you listen to a song (if it's a popular song, you probably don't like it, I would guess based on what you've revealed so far). Do other people like experiencing that emotion? If so, why? Or are other people getting a different message from the song? If so, what sort of mind and motivational/emotional structure might they have such that the emotional and conceptual message of the song appeals to them?

Well, I have never bough music or downloaded much of it. I listen to the radio regularly for brief intervals and I like most of what I hear, but I don't want to hear the same song again and again and again... I abhor questions like "what's you favorite X?" I like novelty, I expect black swans and change. It's is a bit beyond me how people can play solitaire or minesweeper for decades - are they just killing time (stopping though) or do they still find it interesting? I basically play games for their narrative, cheating all the way, and then don't play them again.

I realize that the process I'm describing takes work, but for me, it was about a hobbie's worth of work. Just make people your hobbie for a while. It helps if you can enjoy this hobbie as a challenge. People are actually a really fun puzzle.

I've actually read a dozen or so books "on people" - I can be damn charming (I'm also tall, fit and attractive - which really helps people trust me) - but the biggest challenge is overcoming my own annoyance and boredom and maintainng meaningful relationships. Especially since I believe I overrationalize everything and that others are guilty of the same sin. So getting close and personal with someone is more a task of editing and maintaining your illusions of each other, not so much about truth. Wasn't there a recent study that showed people will predict the behaviour/preferences of their spouses or close friends with marginally better accuracy than total strangers - ie that intimacy is the act of applying your personal self-serving biases to others?

I like to believe I have an underdeveloped herding instinct. Some animals live alone, some together. It's fine.