Also, reading over both your posts again, I am definitely seeing a lot of sociopathic and pseudopsychopathic characteristics!
The only thing about a sociopath that he does not display is anger. He doesn't get angry easily, he gets more frustrated/sad, which is what leads me further to believe that he really is kind-hearted on the inside (or at least used to be).
As for pseudopsychopathic, he is often noting how he is "a guy" when referring to things such as "keeping feelings inside". He is into art as well, and gets emotional during sad movies, but rarely explores the subjects. (Note that he is also hugely into sports which I just pass off as just a regular characteristic of his.)
The thing that makes him different than other guys (in my opinion) is that he is readily aware of all these things. He knows that he keeps feelings inside (he didn't used to, but made a conscious choice to after "learning that it didn't work out well"). I think he's just afraid (or has been afraid for all his life) to be himself. To know when it's okay to show feelings and when it's better not to.
Lastly, I have a related but separate question:
I understand that most people act differently around different groups of friends. That's why people say "different friends for different things". But at what point does it become sociopathic behaviour?
Thank you all so much for the help. You are really making a difference

-Venn