@dounuts7975,
Make friends. Not just with him.
I know - socially awkward - I get that.
But here's the dirty little secret, okay?
No one is born knowing how to talk to anyone. We all learn through trial and error. There are no books and there are no manuals (yes, there are both, and they are essentially useless in the field - don't waste your $$).
The trick is - tada! - talk to people. Male people. Female people. Young people. Old people. People you want to date. People you would never want to date.
It. Does. Not. Matter.
This is a thing you need to practice, to talk to people. And that includes him. But once the practice is in full swing, you will find it easier to have conversations with people like him precisely because you have gotten some experience under your belt and you won't be going in blind.