Ruby actually laughed, giggling in spite of herself and in spite of all she knew about Angels, just amused that he could be so deadpan about something. He really was entertaining. But she still didn't have her answer about how any of this was possible. How she could so easily just talk to him about things Sam had issue with. She supposed it was closeness to the situation, Azazel had done more to Sam than even Sam knew yet.
"You think I'm doing okay?" she asked, sipping at the whiskey and calling for the bottle as Castiel finished his.
"I mean, in terms of the whole thing, I'm well aware I'm the first demon ever to do this. Ever to actually completely switch sides, and its sort of terrifying. I don't want to dissapoint him by messing up." She poured more to drink when the bottle arrived, more for both of them and met the unflinching gaze of the angel, having to fight to keep her eyes human. This would be a bad place for her to go all black eyed.