Am I over thinking this entire situation?

[king]

I think you should make it more obvious to him, some guys might not get they flirt or even see if their feelings are mutual. You know, guys that maybe don't have as much experience dating. So maybe just drop a couple hints that you're interested too. If there is a dance or anything coming up ask him about who he was planning on taking and mention you haven't been asked yet. If you and you're friends are hanging out, invite him along, spend extra time with him. See what comes of it. We live in the 21st century and nothing says a girl can't ask out a guy. You never know.