He would?. He'd see it as her doing something good that she hadn't wanted that kind of power? Yeah he was officially weird for an angel. And she liked it. They needed to make more like him. Even if he looked like some kind of accountant and din't understand about getting drunk. He could learn, Ruby and her boyfriends entirely illegally obtained credit card would see to that. Poor Sam, he'd glare. But then he was cute when he glared and couldn't stay mad at her so it all worked out.
"Hey" she said with a laugh, "I'm perfectly fine with you forgetting what I am, it'll help you resist that ingrained urge to smite and since Ruby is not for smiting, it all works out. But, yeah...I'll take the compliment, I really am trying, hard as it is". She thought she was getting to him a little, she hoped she was, as she watched him with the glass, but the whole template thing threw her a little, she didn't agree.
"I told Dean once I remembered being human. I don't. That template? I don't know it. I know I was a witch. I know I was a whore of a witch that sold my soul to a demon for power and wound up in hell. I know I broke early, I know for centuries I was a torturer, and tortured, and I know I became what I am. I'm Ruby, I'm not...whoever she was. Not anymore, and by all accounts she wasn't much of a human. She was nothing worthy of me using her as an example of humanity. I'm...kind of looking to Sam, whatever you upstairs think of him, he's good. He's so good and he tries so much to break away from what Azazel did, what I helped with. And, well, he didn't follow orders did he. Dean yes, but Sam, he wanted something different and he very nearly got it"
And had it ripped away, his life had been planned out, demons placed in his life to watch and point him in the right direction and he didn't even know it. But that wasn't a conversation now so she put it aside. "You're gonna be okay Cas" she said, shortening his name, purely cause, well if the boys could do it why not her. "Now, have you ever tried Guinness?"