"Mmm." Sam smiled faintly. He was watching her, making sure that Ruby wasn't having difficulty. The illness could easily worsen at any time and Sam wanted to be entirely aware when that moment came along. "Very observational of you. It's a habit." She was accurate with those observations too. Sam was surprised by it, but not entirely. They were getting to that point where they knew each other well enough to even call out little, tiny things like that. Sam knew she had her own quirks and habits, like that look that automatically came across her face when Dean came around and the way her mouth tilted upward just that much when she was amused. He knew it well.
"As long as you like it," Sam said, pushing his mouth to the side of her face. He kissed her cheek, then the top of her hair. His fingers replaced the spot his mouth had vacated and Sam quietly stroked the top of her head, hoping to help ease Ruby into that unconscious state of slumber that she so clearly needed.