By opening up to Dean, Sam has helped him accept things and chill out as well. It normalizes Sam's relationship with Ruby in Dean's eyes. Sam will learn that most everything John does has to do with Mary. It always has. Part of the reason everything is going so calmly is that John regrets so much of what he didn't do when he was alive back home. Itinere has given him a new perspective. John's brows raise at that and he chuckles. "Is it? I don't have much experience with you boys and...girlfriends." John probably looks like he's been thwacked upside the head too hard too. He is surprised this is going so well, surprised he's saying the right things.

John nods a little at Sam's suggestion. "Yeah. That's probably a good idea."