Seems they both have the same idea about spending the night together. He hadn't any plan for how to deal with Nurse Penny if she peered into his room other than to have Ruby hide or pretend to leave just then. He'll thank Ruby for that should he find out that she paid the night nurse off.

He can't take his eyes off her when she comes back in. Not to spoil the mood but, "You changed." He also notices right away that her lipstick is the same shade as her dress and he takes it all in with a crooked grin. "I like what you did with... Everything. Hey!" That's been their hello since their Wessen and Deville days. Spoilers: he likes just about everything about her, except has at one time or another admitted she shouldn't ever do pigtails.

"Penny, who?" Part of that is him being facetious, but he can't and won't think of other women now either. Rather than focus too much on his hospital clothes by comparison, he brings her attention to the set up he made. "This is for you... Us, rather. I thought we could have a little date while... while, well, something can be done." Yes, he has faith Dean could find something to help him. Meanwhile they deserved some time together while he was lucid today. "Sit, sit please." Anywhere on the bed would be a good start. He sits next to her.