You can overcome shyness with exposure therapy. Do the things you are afraid of, and take control to have a more rewarding life. I, too, vote number on cup. 🙂
Lemme tell you, guys don’t get enough attention /compliments from girls and it’s not too often that girls take the first move, so just by doing that will make him super happy, even if he doesn’t actually like you back (but by what you’ve said it seems like he does) he will still be super flattered.
If he does end up rejecting you, you’ll feel embarrassed for a little while but your confidence will shoot just for the simple fact that you made the first move! And you’ll boost his confidence too!
Like someone else wrote, write your number on his cup, it will save you the awkwardness of actually telling him and it’s also super cute!
Good luck girl!
I married my customer. What I did was start to make it super obvious that I was going out of my way to talk to him. If I wasn’t going to be the one taking care of him I would make an obvious switch out with my co-worker right before it was his turn. I’d use his name a lot. Lots of eye contact. I’d always say, “It was nice seeing you” as he left. I’d actually plan out things to say to gauge his interest in things I like. For instance, I’d say, “It’s going to be great hiking weather tomorrow” to see how he’d react. Then one day he used one of my conversation starters as a way to ask me on a date.