Most Helpful Guy
Grab those maraschino cherries you got behind the bar, find one with a long stem, tie it in a knot in your mouth. It doesn't take too long to figure out if you've never done it. Or ask him if he can tie one himself and hand him a cherry. I don't know maybe that's weird? But I could see that being an innocent opener headed in the right direction.
Or when he's does tying it, snatch it from him and pop it In your mouth quick and swallow it, maintain eye contact throughout. Leave a moment of silence and then with a wide eyed gaze say "now you're a part of me forever 🤫" make sure to include the 🤫 at the end. Should spark a connection and get him feeling comfortable, relaxed and open to conversation.