It's a delicate situation so I would want to handle it real classy.
I'd ask him to go out for dinner. Somewhere nice. Maybe Applebees.
I'd order for him. Show him who is in charge. I would go all out though, splurge a bit. I'd do the 2 for $22. Order up some chimichangas, maybe get an app - onion rings, extra sauce.
Then, after we got a little bit of a buzz, finished our food, we'd retire to comfier confines - Paradise Found. We could have some cocktails, enjoy some dancing - and then, I'd let him walk.
He'd have the best night of his life, and he leaves on a high note. Everyone wins.