I'm awkward and can't get a date. Advice?

(It's long please bear with me) I think this one dude is cute, he's in the marching band at my school. I feel like everyone likes him. I've known him since we were sophomores and this is the beginning of my senior year. I've never been a romantic and haven't really been in a relationship since middle school, if you can even count that. I tried going on a date with one guy but he was way too into PDA for me and I get really uncomfortable in those situations. However the marching band dude (let's call him Rachel) is really easygoing and his first and last relationship was pretty relaxed, as far as I know. He seems hard to get and doesn't like to communicate that much. We're into some of the same stuff like heavy metal and band (I'm not in band though). Anyway, I want to go to prom with Rachel but don't want to ask him. We've got a long way to go until then. Any advice on how to talk to him and just be chill and not nervous? Or how I might make him like me? If he's a nine out of ten, I'm a four. Weirdos call me pretty but I have acne pretty bad.