Search Results: tell a girl you barely know that she is pretty

Our relationship is far beyond friends with benefits. We have developed a close emotional connection. He is very emotionally attached to me. He says sex is not the most important part of what we have. We do stuff outside bedroom, we talk on social network or in person every day about everything.
Here is the confusing part. He said we doesn't want relationship 3 times before, but behaves like he is my boyfriend. Recently he wanted me to answer what I think about his personality, what is the value of him to me. He wants to do more for me emotionally, as he thinks he is of barely no use to me. He said I complete the gaps in his life and am very close person to him.
He got mad when I said I went on a date with someone else (I did). Like "If you want to build up a relationship, then you should first stop being with me". Later in the conversation he changed his position and said I can go on dates, but must tell him about it. He will leave if I sleep with someone else. He said he won't search for relationship and won't sleep with anyone else either.
He is overweight and doesn't look that good to other people. I'm quite pretty skinny girl. He knows I get lots of attention from other guys (I mostly ignore it). He sometimes says I'm better than him. He thinks of himself as an "old piece of shit" (exactly what he said), so has low self- esteem. He said he doesn't want relationship because he doesn't think he has enough resources for it, since when he is in one he does everything to that person. But he wants to make me feel the same good as I make him. He hasn't been in relationship for over 2 years, doesn't emotionally open to any people (except m somehow).
I don't care what other people think of him. For me he's amazing. If he has no feelings for me, I'm probably just gonna leave things as they are, as it's better than nothing. I'm scared to confess, as he said he doesn't want relationship. I never told him I really want one.

There's this guy; whose family is pretty close with mine. He has changed a lot since the last school year. Great quarterback and carries himself differently than most HS boys; dresses sophisticated, never says vulgar things. He's never had anything to do with girls, since his dad is so strict on him and football; also he's a little shy, barely has anything to say most of the time. A guy friend of mine told me that in the locker room after we won the game that he was pumped and said do you know what I wanna do? And they all said what and he said get laid. Lol then they all screamed hell yea. It was a surprise to most of them, because he never says things like this. Well anyway, I've never really had a bf so I was considering trying to talk to him. I feel like an advantage would be our families, but I'm not sure about that. Maybe his mom could talk to him about it? What do you think I should do?