OP here,
Thanks for all of your advice. I really appreciate it.
After taking your suggestions into consideration, I was seriously considering asking him out, despite my reservations. However, he's been acting really weird recently - mean, even. I know he (and some of his friends) have started taking shots at me to my face/behind my back. I'm kind of a shy, introverted person to begin with and I don't think I can summon the courage to do it now, even if I thought I could before. :( This kind of sucks. Thanks anyway, 4-ch.