Search Results: conversation ideas, what to talk about

I kind of have a crush on my old high school teacher, he was only my teacher for a year and now that I'm over 18. I want to reach out, even if it's to talk in a platonic way. There were only 5 students total in the class that he taught me and honestly, he wasn't a very good teacher to me. We had lots of off topic conversations, sometimes for a very long time because other students would always be late. When we'd bump into each other outside of school hours, he'd always come to sit with me and talk and we've had many long conversations together. I think that he's someone that I'd like to be friends with even if nothing else develops. He's in his 30s and was single last I spoke to him but it's been more than a few months now.

Should I reach out at all or would this be a terrible idea. I know this sounds like a terrible idea but I'm wondering what other people think. Thank you for the opinions in advance!

So I have liked this guy for 2 years and during the first year, I told him and he told me that he did not like me but he could see us together. Which I was confused about but I didn't question him anymore about it. But we would talk all the time back then. But He is always busy now and isn't a very good texter. Everytime I see him, he is either busy or I just get really nervous around him and I don't know what to say to him that could lead to more to talk about lol. When we do talk, it seems like he doesn't give me direct eye contact at all. Almost like I'm not there but I do this sometimes too when I am nervous but I have no idea what he means by it. But he is so nice and respectful towards me. Of course that doesn't mean he likes me back. I'm not really afraid of him saying he doesn't like me back. I guess I'm more afraid of the awkwardness that could possibly occur during the conversation.
I guess my question is, should I bring this up to him again considering that I already did 2 years ago? Or should I not bother him about it anymore?