Look, you obviously want to go for it and have some kind of situation under the radar. Frankly that sounds like motel hookups out of town. Do you really want that? Wouldn’t you rather just meet available men online?
But if you do, yeah, you’re going to need to be that direct. Asking about insurance or posting topics online is going to be completely ineffective. Touch his hand, give him a look, laugh at his jokes, then ask him if he’s seeing anyone.