Sam has had friends before. He doesn't need to know that he can make a connection outside his family the same way Dean does.

Just idly musing, but... how long has it been since Sam has actually had a "friend"? The Stanford people were years ago, and they never really truly knew him (not to mention Brady was possessed by a demon). To paraphrase what you said about Dean: "(Dean) is not his friend, no matter how well they're getting along. He's (DEAN), for one, and that's tied up in love and obligation and guilt and all kinds of repressed Winchester crap. Even Bobby's not his friend, although (Sam) loves him -- he's a father figure and a resource, and (Sam) knows it. Jo and Ellen were never friends -- they were comrades, they were coworkers." (And I might add that Ellen and Jo were presented as favoring Dean -- in their last few episodes they barely even spoke to Sam. And Bobby... Bobby, I love Bobby, but I don't think I'll ever forgive him for telling Dean that he's Bobby's favorite.)

Anyway, what this totals up to for me is that Sam is totally isolated and has been for a long time now. I am relieved that he and Dean are close again because other than that he is so completely solitary. Yeah he went to college, and apparently had friends there. Years ago. That he hasn't spoken to for years. People who didn't really know him, who know nothing about him now -- not what any of us would call friends.

So he's every bit as alone as Dean. Maybe even more, if you can actually consider Castiel a friend of Dean's. (I'm waffling a little on that one, since Castiel is kind of hard to get in touch with and doesn't always show up when they'd like him to do so. He's "friendly," but maybe not really a "friend." And maybe I'm just playing with semantics.)

I'd say Castiel is an unfriendly friend. They're antagonistic, but they're not broken up. They've got each other backs.

Sam was able to share bits of himself with Rebecca, and even with Sara, in a way we didn't really see Dean share as he went along. Cas was the first comrade in arms that he described as a friend, the first anything he described as a friend, after having mocked Sam for similar. So Sam is operating from a position of loss, and Dean is operating in a position of dysfunction.

The difference for me is that even though Sam is isolated and probably feels it a lot of the time, he has always made outside connections. Even as a child, per After School Special. He probably wants someone now, too, but it's also not the best time to be making new acquaintances on the outside, you know? But for me, he *knows* he has that capability, whereas I don't think Dean did.

And with Dean and Cas, I was mostly going off the fact that Dean actually told Zachariah that Castiel was his friend. Even if they're not poker buddies at the moment, there was a time when Dean realized that Cas meant something to him no one had before. I just find it noteworthy for him, and ridiculously touching.

Well, Dean doesn't run around having more profound bonds with everyone. He's not an emotional slut.

Oh, I loved that scene so much. Every last word.

End to end, it was a thing of beauty.

he has always made outside connections. Even as a child, per After School Special.

I thought that particular school was an aberration precisely because Sam made a friend there and because a teacher took an interest in him while he was there. It showed that it was not a usual occurrence for him.

Sam's good at talking to victims and putting on a veneer of charm and getting along with people. But other than Rebecca way back in "Skin" how sad is it that the closest thing to a friend I can remember Sam having developed over the course of the series is Ruby, who turned out to be demonic bitch that needed to be stabbed to death with the phallic knife of doom? Sarah from "Provenance" had so much potential, but they never brought her back for more than the one episode.

But that's more than they've shown Dean being able or willing to manage. He has no Rebeccas, people he lost touch with, no Ruby that stalked him for two years and lived right up there with him every day, nor a Sarah that they might swing round to--not until it was revealed he had a holy grail of a pre-packaged family. Where he made a friend. And look how that turned out. Castiel was the first shot at connection past/without sex.

Well. There was Cassie and the homicidal racist ghostly truck. (That obviously wasn't a past without sex, but then Ruby wasn't a past without sex either.)

And she dumped him twice. Double your pain, double your money.