Does waiting ever work out?

I'm honestly lost about what to do at all about this. Me and this guy have been friends for over two years now. He used to tell my friend that he liked me whenever she asked and he can picture himself with me or something like that. That was right before summer 2010. Usually over the summer his mom (she's over protective) keeps him from doing a lot with anyone except his one guy best friend. So I didn't see him at all that summer. Then school started again and even though we didn't have any classes together but we basically spent every break with each other between classes. At the end of the year this year I ended up having a lunch with him, but him and his friends were the only ones in my lunch. He told me he wanted me to sit with them and he didn't want me sitting alone, so I wasn't exactly sure whether he really did want me there or he just didn't want me sitting alone or whatever. Eventually I stopped sitting with his friends and he basically chose me over his friends and sat with me over them and I kept asking why he was sitting with me when he wanted to be with them. And he said he didn't and he liked it better over here with me. Whenever he's around his friends he gets really talkative but when he's around me he gets really quiet and he says it's cause he can't think of anything to say. Then, he invited me and my friend over his house cause he lives on a lake and has a boat and a jetski. So we went over and his parents automatically knew who I was but they never explained why and that was the first time I've met them. And they favored talking to me more over my friend. And he said at the beginning of summer we should hang out again but we haven't texted or talked at all yet and it's been a few weeks. He's told my friends again that he supposedly does like me and his friends told me he talks about me a lot and they make fun of him whenever I'm around. But he says he's not ready for a relationship or something and he has to be sure he's ready. But he never tells me any of this. It's always my friends. And I'm really confused about all of this. Can anyone give advice with this?