WHAT IS GOING ON????

I need some explanation because this boy has me so so so fucked up. Me and this boy talked for a a few months and dated a few years ago. This was my freshman year and we only officially dated for about 2 weeks.  But after we " talked" for a few months. He and I then had the discussion where he was afraid that he would break my heart. And that we both needed to move on.  He then got a girlfriend for two years. He and this girl did not have a health relationship and they needed to break up. He would always talk to me about it. Around this time I had just gotten my heart stopmed on by another boy.  He countined to tell me that if any boy where to ever pick any girl over me they were out of their minds. I was going to make someone so happy someday and he would always be jealous of who it was. He said how I can't be so chill with who's my guy because every guy is going to take advantage of me. And that if I put my all into a relationship that I was going to be so happy.  He told me not to b afraid to put myself out there.  Over the most recent summer him and his girlfriend  broke up   We started talking more and more.  He always jokes about us ending up together.  When ever he sees another guys name on my phone he tells me to not talk to them because they a shitty person or something.   Or not good enough.  The other day I wore leggings to school and he told me to cover my ass because all the boys didn't need to be looking at me and that I'm different from the other girls that dress that way. He also asked me who my dream guy was. When ever somebody brings up his new girlfriend around me he will not awnser and told me before they dated they were only friends and always asked why I cared now ? My friends have asked why we just don't get to get her and he alsways says he knows but he has a girlfriend right now. That's most of the story.  I just need some help to know how he feels. Should I tell him how I feel or am I in the friends zone.  How do you think he feels about me ?