You were his obsession - but he couldn't admit it to anyone.
He wanted you. He really wanted you.
Chris was one of those popular guys at school who put up a tough persona but really had a whole personality going on inside. He didn't care for the girls who threw themselves at him. He wouldn't even date one while he had this obsession with you. He wanted you. The girl who didn't even look at him. He was obsessed with you.
He was attentive, too. He knew everything from your school schedule down to favorite color. He knew when you were dating someone - which wasn't very often, since the school you went to was filled with arrogant douche bags. He knew the facts, but he didn't truly know you. He really really wanted to, though.
Even though he was obsessed, he wouldn't admit it to anyone. You were quiet. Reserved. You only had a few really close friends. If Chris was seen with you, his rep would go down. Not that he cared. He just didn't care for his reputation getting destroyed AND ** for you to reject him.
He didn't know what to do.