Boy I like

Can someone give me some advice? I've liked this boy for a while now and would really love to be closer to him and get to know him and stuff. The thing is I'm so shy. And he's part of the 'cool popular group' and i'm more like an underdog (well, the cool underdogs who hang out and have fun together). We shared a week together while doing some community service/volunteering and I notice that he's the sweetest guy on earth (let alone the Colgate smile)...I know I should talk to him and try to be friendly but the last time I did that the other dude basically stabbed a knife though my heart when I told him how I felt...sorry to bore you with my teenager sh*t but I could really use some help!