Sam would agree that it does make it tricky to offer any useful advice. It goes without saying that his relationship with Ruby isn't exactly the kind that took its time developing. But obviously it's good that it isn't stopping Dean from talking about it. Though, his advice can't be that bad either. Slow and steady can't hurt anything. Sam's reaction to Dean's eyes is to pull his head back and lift his brows. What was so bad about talking? "Yeah, sort of a cross between a date and discussing things. The case is just an excuse. ... Be yourself. Don't try to sleep with her right away."

Ruby and Sam try to make time for each other every week for exactly the reason Dean thinks. Their relationship is better for it. "Well, you probably should take her out to a movie. It's possible she's not going to think anything of it if you ask her to join you for one here. You never know who's going to be around." Or is Sam just making excuses so Ruby and himself have higher chances of having the bunker to themselves.