I'm likely to befriend him only and ignore the rest of what he wants, as it's his turf. I wanna *know* him. I have this anyways with the partners I select, but with him, I'd wanna know it all. And, I am normally not known for my patience, but in this case, I have oceans of time. If he's interesting enough, I'm in no hurry. I'd wanna know it all. Quid pro quo games, playful banter on a platonic level, and *any* time he goes back to playing his game, and go sexual, innuendo or whatever, I'd ignore it, be utterly oblivous to it and not let it affect me. I know..this, coming from me is ironic, but yeah. Coz it's the only way to show him there's more to life than powerplay. It's fun, for sure, but it's not what a relationship is built on.
The goal is to let him know that I like him for who he is, not what he can do to me. Not the cheap thrills (while mightily fun) that he provides. He's more than that. And, my main prize? It would be his trust. That's what I'd set out to get. I'd not be interested in him sexually till I get it..and till he's proven to have earned mine. As I said..quid pro quo.
Ultimately, I'd listen, without being judgemental and I'd wait. If he runs, then I wasn't the right person to do this for him, and we might not have been a good couple anyways. If he sticks around and puts in the time, you as well as he might just find what you're looking for
Btw. You'd better know what the f** you're doing, if you're going to go down this road, or be ready to have your heart torn out. Those are the stakes, my dear.