What do you think...does he?(Girls & Guys answer)?

Okay, there is this boy and well, he works at my moms work. He is 16 and I am too. Everytime I go out to the retunda(middle of a courthouse) he stares at me and smiles. Yesterday I was talking to the security guard and Jared(the boy) was on the 3rd floor and he yelled down to Joe(security guard) and when he thought that I wasnt looking, he winked and said yeah I do. and then he came down on the elevator and it stopped on the first floor so that this woman could get on and I just happened to look over there and he smiled at me. The thing is, we are totally opposite of eachother, I am shy and quiet and he is just outgoing. And he goes to our rival school. Do you think that he likes me or what? Any help would be great because if majority thinks he does, I will go talk to him (: Thanks in advance!