I asked my 15 year old son about this so I could give you expert advice!  He is a very smart kid-honor roll-football- as well as trak.  The guys like him that are smart-funny- and average looking-cute but not super HOT always seem to have a crush on that POPULAR skank that all the other girls HATE with a passion!  He says its a guy thing.  He says you should find activites that he likes- ask his friends-or yours- and find ways to be at the same activities he is at.  If he skates- show up at the skating rink- if he likes video games-learn his favorite game and ask his advice on it.  Make his likes YOUR likes.  Dont jump him and scream I LOVE YOU!  My son says he will run like crazy!  lol  Let a friendship with him start and then he may begin to look at you in a different light!  Good Luck!