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Why do you want to do anything at all? How about respecting his boundaries? That would be good start.
It's not a bad thing to try to bring your kid's boundaries further out. It can be socially good for them to be more open. Then they won't end up like the guy in the meme
That's just wrong. If you try to push your kids limits without teaching them respecting boundaries and talking to other people respectfully, things like the guy in this picture will happen.
It's okay to have boundaries and we have to teach kids to communicate them in a respectful, firm and friendly manner.
It is not just wrong. Being respectful of boundaries and trying to push someone's boundaries aren't mutually exclusive. Every person has their boundaries in different places, and if you're not willing to compromise on the small stuff you're going to be the 'fun brake', the guy who causes the innocent fun to slow down to talk about how much you don't want to do it.
Don't get me wrong, there are absolutely boundaries that need to be respected. But there's a difference between something you feel awkward about and something that's against your principles. Pushing your boundaries to eat a meal that you don't like but is otherwise safe isn't the same as pushing your boundaries to get drunk/high.
Another thing is that for the most part, when people try to persuade you to share something slightly personal like music, it's not because they're dicks who are trying to make fun of you. Chances are they're trying to include you in their group, trying to bring you into the collective, trying to become closer friends. They're looking for something to bond with you over. Discussing occupation, education, and personal interests are probably the most basic way to do that.
While I agree with a lot of things you said I disagree with pushing boundaries.
People that are really interested in him will find a different topic to bond, it's not like music is the only thing on earth.
Also it's okay to be the fun break, it's a chance to get feedback about that and realize you need to find a different social circle that fits better to your own life. Or figure you push your boundaries yourself if you really want to belong.
But nobody has to fit in everywhere and if his boundary is his taste in music then who are we to question that?