The whiskey was... orange. Ish. It smelt sharp, clinical, not unpleasant. Perhaps when he had seen more of the world he would be able to draw comparisons to peat, or woodsmoke. It was not a 'new' discovery, finding that humans could take enjoyment in observing when they ordinarily seemed so dead set on charging into things, but it continued to surprise him.
“Of course he is.” Was that a sly smirk around the glass? Maybe the shadow of one, because Castiel did not smirk. “And is fully aware of that fact. It is very generous of him.”
It was a mark of... well, something, no doubt (whether you termed that something 'progress', 'falling' or simply becoming as jaded as the rest of Team Not-Lucifer dependent entirely on perspective) that Castiel could listen to Ruby talk about her track record in possession and rebellion without recoiling in disgust, where once merely being in the same room as something of her ilk would have him in the smiting mood. Having the glass cupped in his hands helped, the weight of it surprisingly grounding (maybe, given time, he'd come to appreciate why humans drank after all).
“It is my first time.” Cas admitted with a small shrug, taking a smaller mouthful of the whiskey than he had last time; obedience was easy, and Ruby's instructions gave him something to follow. “I do not think this place was settled the last time I walked. That was in the Days of Jared, when we smote Semyaza's children at Hermon. There was... little time for tourism.” Another not-smirk, and another mouthful.
… oh. Was that the burn she had meant? Interesting.
It did not seem strange, talking about his past. They might as well have been two grizzled veterans exchanging war stories. The only complication, really, was that they'd served on opposing sides.