Should I tell him how I feel?

There's a guy I've known for 6 months now, and I really like him. He's admitted to me that he liked me when we first met, and I feel like he still does. He's constantly saying I'm pretty, a great person, out of his league, and even said he felt like I should have been there when he and his family decorated their Christmas tree. He treats me like a princess. I've kind of told him how I feel, I've told him all about how much I like "this guy" and basically described him, just never said his name. The only problems are that he's 14 while I'm 16, and we go to different schools but live in the same area. Also, my friend has known him longer and likes him just as much. She said he liked her before, and he gave us both gold lockets. Hers has diamonds and it's smaller than mine, while mine has flowers on it. Last night, I told him I'm not sure if I should tell "the guy" how I feel and he said (I'm typing it straight from his text, but it'll be added on as extra because I'm running out words.)