I may be an old man but things haven't changed.

First you have to decide if he is worth it. If he is offended and you lose him as a friend, was it worth it?

Consider the consequences. If it goes down wrong. Will the knowledge of this totally ruin your year? Are you willing to suffer any negative consequences that might happen?

If you really want him, sooner or later you have to "hit' on him. Do it in such a way that you can say you were joking if he is offended. Make a small hit, not a grand slam. You know what the signals for a "hit" are in your town for guys your age. We don't.

Only you know the answers to these questions.

Good luck. If you go for it, I hope you are happy with the results.