Something about that way she says it. Her voice is fond, but her smile is sad in a way that he's surprised rouses up something. It's not sympathy exactly, but some sort of feeling that he can't quite put his feeling on. Honestly, he's not great with feelings anyways.

He pours her another drink when she pushes the glass forward before sliding it back over to her with an awkward smile.

"So the universe dropped you off on a roof of a guy who's a version of the person you miss more then anything. Now that seems like it's playing a joke on you, no offense," he says before taking another drink of vodka. She hadn't actually said those words, but that was the vibe he'd gotten from the last comment.