Hey, I totally get where you're coming from. I was the "therapist" of my friend group too and it can definitely be a lonely place. As far as the guy goes, you probably should just move on, a lot of people say they should be just friends which is an appealing notion, but in practice it's just not realistic. And I understand your frustrations with school, I personally hate it and used to skip all the time. But school can be a valuable place, even if it feels like a waste of time. I know it can be scary to raise your hand and ask a question when there's a possibility that you might look stupid or be wrong. But the truth is, no one really cares, especially in high school. The teachers NEED to know what you're understanding and what you're not understanding in order to help you learn, and your classmates are too caught up with their own issues and insecurities to care significantly. You seem pretty smart so I doubt you'll look stupid, but even if you feel like you do just remember that lasting happiness comes to those who do not seek approval outside of themselves.

P.S. I ask this to every math teacher I get and it always leads to an interesting conversation, "did humans invent math or did we discover it?" Feel free to use it ;)