I'm so confused, what should I do?

So, about a month ago, this guy started talking to me on FB. We went through the whole "what's up" "nothing much" thing, then he asks me oh-so-subtly how me and my bf are doing. Well, I've never had a bf, even though I'm probably pretty enough to get one, but I'm so shy and no guy ever seemed willing to break through the shell. Then he said "as cute as you are, I thought youd be asked ot everyday :)" and it was impossible to not be flattered by that, y'know? Okay, so I met the guy when school started back, and I had a mini-heart attack because he is this ridiculously cute football playing sopre, and I'm just an uninteresting freshman. He walked me to all my cles for a couple days, and I thought he was amazing and sweet. But then he insulted my best friend And I got more upset than I should have, mostly because my life was being crap, I was confused, lost, and felt utterly hopeless, and I'd been picked at plenty in elementary. Then I did something stupid--I avoided him. It's been a while, but I really think I've got my life back on track. I was an unconfident, quiet, nervous girl before, but I really think I've grown up some, and am not as shy and reclusive as before. So, do you think I should talk to him? I really want to, since there will Be that irritating "What if" there if I don't, but I'm not sure if he'll want to listen and consider starting over like I want to.