Ok, now my calousness kicks in (wow, you esablished something rare!)
#1. He's a guy. C'mon, its not rocket science here. Just say "Hey, you got a girlfriend, cause I like you a lot, and was thinking of being the next one in line" or something like that.
#2. If you use subtle hints, you'll only confuse the poor fella. Have you seen that new book lately about how much men know about women. Lemme tell ya, all the pages are blank.
#3. Speaking from a guy's point of view. Work that ass. It stimulates the mind.
FINALLY. I hope it all works out, good luck to you.
It is impossible to love and be wise
-Francis Bacon