Why are boys so confusing?

Ok, so I've gone through a lot of history with this guy. I've given him three chances because and he was always uncertain if he wanted to be with me. Yet, I've never lost interest for him for some reason because I knew he was a good guy.We ended not talking for five months after the last time. He eventually asked me to junior prom. I said yes. He promised my friend and his best friend that he has changed and will not break my heart again. We went out for almost two months and broke up a week ago. Days before our break up, he wanted to talk to me about something that was bothering me. He said that "when he looks at me, there is nothing that stands out to him." He wanted me to open up to him more and let out my true self. I'm a pretty shy girl, so I understood what he meant. Yet, even after we talked I still felt like something was wrong. I talked to him two days after that to ask him about that line he said to me. I also thought he was being a little bit of a hypocrite because he never opens up to me or even tried to get me to open up. I asked him what he liked about me. There was a 30 second silence and he said I don't know. What is his deal?