Re: later on;
Ruby had been on her way over to check on Sam when she had heard her own voice. It was inside her head, bringing up the memories of that first night with Sam. Memories that she hadn't wanted flashed all around the people in the warehouse with her. Least of all John. The things it was saying about Dean had mostly washed over her, she figured thats what he'd been doing in hell. She wondered how long he'd lasted, she knew more about Johns time in the pit but Dean had come out of it suprisingly stable, she figured that meant he'd caved. Started making people suffer in place of his own suffering, everyone caved. Dean didn't show it though, that sort of almost impressed her.
And John was hurting, bleeding. But he'd known the risks. Ruby had explained them, so she didn't feel bad about that.
"Might want to stay out of my head in future, or at least focus on the good stuff, like the fact you know exactly whats gonna happen to you. Because I know what Sam's capable of. You can see that too can't you"
By now she had reached Sam, ignoring the others, even Heather, even Dean and knelt down at his side.
"You're doing well, very well for not having done this before, You just gotta break through, get it once and you have it, get it once then its only about focus. I've seen you do it. Don't listen to it, just focus on pulling it out of John, he'll be fine. You gotta trust me"
She looked around momentarily
"Might have a better chance without...distractions" she suggested calmly