He is interested! Look in your newspaper for the Parade or whatever it is in your town that tells about what's going on around town. Find something that you are interested in, and the next time you see him, ask him to attend it with you. If he says no, say something simple like, "Perhaps another time, then?" and leave it at that. This way, he knows you are interested, and there is no "let's go as friends" or "let's go as a date." Be PREPARED to pay, just in case, but hope he pays for it.
Ask him, just draw in a big deep breath, and ASK! Find out one way or the other so you can move on, either with the ability to let go of wondering, or as his new girlfriend-to-be! Be brave, don't push, just ask, politely and in one sentence.
Would you like to go to the Dinner theatre with me Saturday evening at 8pm for the showing of "La Belle Du Monne"?
"No, I'm sorry, I have to work, but I am free on Sunday."
"Excellent, perhaps lunch on Sunday, then?"
CONGRATULATIONS, you have a date.