Ruby leaned in to watch him with interest. She watched each line he drew as he spoke, and when he slid it across the table to her, she grinned at him and took it. "Wow, you're officially my new best friend. Who would have thought?"

She picked up the paper to look at it again before shifting to tuck it into her back pocket. "Angels were only just deciding to pop up right before I died, so I have to admit I'm a little clueless in that field. And as for Sam? Don't worry, where there's a will there is a way and my will is like a fucking giant. Besides, he is a walking tender spot, didn't you know that? Push him in the right spot and he'll go miles for you, all on his own."

Ruby moved to take her glass so she could take another drink, before offering that same charming smile from before.

"The only thing left for you to tell me is what kind of boundaries I need to follow? Who do I avoid? I don't know who your friends are, or aren't, after all. Aside from Castiel...?"