John really needs this drink.
It isn't as if he isn't wise to who Eve is, to what she is; or even ignorant to the fact she once impersonated his wife in order to hammer a message home to his sons. He's incredibly aware of it, in fact, and if this drink is all pleasure and no business he'd be very surprised. He's interested in what brings the mother-of-all to flirt with the grizzled father of what he suspects are some of her least favourite humans, because he's under no illusions that she doesn't know who he is, too.
But she is charming, too. Beautiful, witty, enough to actually have his interest - and he really does need this drink, needs the company. The mess with Dean... John shakes his head and puts it out of his mind as he waits outside an arranged restaurant, a quiet little place with a good bar. He's early like a gentleman should be, even dressed in the cleanest button up and jacket he owns (you know, the ones with the least blood stains) he owns, but his beard remains untamed, scruffy and thick with grey, and he knows that there's nothing in the world that can take away how tired his eyes are. He's still not sleeping properly, Hell still there in every breath.
He leans against the outside wall, a comfortable distance from the door, his hands shoved into his jeans pockets, one booted foot tucked over the other as he waits on Eve's arrival.