Most Helpful Guy
I say let him take the step. He is the man! So I would not stress about it, just let things flow naturally. He has to WAKE UP and realize that if he likes you and wants something more he is going to have to flirt with you and escalate.
You are doing great though, you are trying to flirt with him now and then and that is great - you are doing YOUR job on the courting process imho. He is the one that now needs to step up.
Continue doing your thing and wait to see what happens - remember, be cool and have him chase you after