Sam is delusional, but Dean has gotten used to Ruby and Sam. He has walked in on them one too many times and now (most of the time( he calls out or knocks before he walks in any room.

Dean had thought he might settle down once with Lisa and Ben, but he'd only put them both in more danger. He'd given up on the idea of settling down after that. It's only recently that he's started thinking about it again and only because Jo is a very competent hunter in her own right. Dean has always been the one that wanted a picket fence life, though he'd framed it as wanting it for Sam because he didn't think he could ever have that. Now, he thinks he'd like something more in the middle. Dean saves people and he's good at it. He doesn't think he could live any other way now.

Dean scrubs a hand across his face. Sam's disbelief and his own doubt working against him. "Nah. I mean...you're right. I should probably just stick with the bar bunnies. One-night stands don't usually get anyone killed."