They broke up, is he ready for me now?

I am a senior in high school. I am afraid to show people i like them so then they lose interest because they don't know I like them. When I was in middle school I began liking a boy, I never told anyone really. Also for me all the times I have liked someone, I really like them, I like them for as long as I am around them and usually even longer until all hope of getting together with them fades. Well freshman year we took a school trip together and I think he started to like me. Lots of girls have liked him and I noticed how everyone who asked him how always got rejected so I decided to play mysterious and I think he fell for me. Sophomore year we started talking to each other and I knew he liked me but I didn't know how to approach him and tell him that I liked him as well, i didn't know how to start something with him I was too scared. Then this girl asked him out to homecoming, I heard him talking with his friend homecoming week about how he had a plan to get out of something then before the pep rally he walked with me and started talking with me, then one of his friends and my acquaintances who also liked him began to walk with us. Neither of us knew what to say and I got scared and ran away. When I looked around he was chasing me but he ran into the girl he was going to the homecoming dance with and she stopped him, i didn't find out that he was going with her until a week later. After that we made eye contact alot in class but I stopped after learning he was going out with someone. They have been going out for two years now and just recently broke up. Junior year and this year I joined a group with him and we have seen each other after school, I have become more comfortable around him but he has become dedicated to this girlfriend over these years. Now that he has broken up with her I don't know what to do. I am now better friends with him but i still feel scared around him. I think he is sad from breaking up and I don't know why they broke up either. I don't know what to do, i love being around him and I would like to be with him more but i don't know what he is ready for and the acquaintance from before, she is now my friend and i don't know if I should let her go for him or if i should. or even if he is ready. i feel like i really love him but i don't need to be in a relationship with him. I just want to be around him alot. What do i do? Also what do I do about college next year?