Ruby kept being pleasently suprised by the angels willingness to try new things. Even decidedly confusing things like whiskey. Because it was confusing. He'd just need a lot more of it. One of Sam's credit cards would cover a few bottles of the stuff and maybe that would actually have some effect. Or she could throw some of her fun-herbs into the mix. Though she did want to get back to Lawrence in one piece and entirely unsmote. So perhaps getting the angel high would have to wait for another day. Though it was on her to do list for definite. He looked confused by the whiskey, though he had downed the glass like he'd been instructed and wow he really did to what he was told didn't he. Ruby didn't understand beings like Castiel, she supposed she never would. But he seemed to enjoy the thought of trying the occasional sin. Sin was more fun if you had someone experianced to try it with and he most definitely had.
"Its interesting isn't it, next one, I want you to appreciate it, smell it first, sip it, see what you make of it. And then we'll move to bottles of it. Sam's covering the tab." In theory. "Humans do this for many reasons, fun being one of them, there's a phrase, drowning your sorrows, thats another. Heartache, celebration, love, hate. Every emotion is cause for a drink to some" She explained as best she could smirking a little when he tried small talk.
"1798, I spent a few years in an Irish Girl during a fun little rebellion they had. Azazel had me out and about in the world searching for..." Well, she didn't need to say, why else would he have had her scout nunnery after nunnery, war after war. "Anyway. Less said about the things I did the better in present company, but to answer your question. yes, I've been here before. And evil as I was or otherwise. I liked the people"