spn20rewatch, 1.11: "Hell, I wish I..."
Well, after a nadir, the only way to go is up.
The long-form conversation of s1 continues here, as the Winchesters keep revolving around: who's in charge? What's the right play? What roles do we want to have, and do they have to be set in stone? Sam's frustration with John's distant orders reaches a boiling point when they're sent to yet another town and it's clearer and clearer that John has no interest in their assistance with The Big Plot, and he's even more frustrated that Dean (as always, from his younger-sibling point of view) is taking John's side. It isn't enough to do these small wheel-spinning hunts, even if they are saving people -- Sam's demanding action, here, on the big revenge plot, but he's also saying: god damn it, am I an equal partner here or not? Are we adults? What's the point, if we're not?
Dean's equally frustrated, because they've been through this before. How many times does the slogan have to be repeated? If they can't help with the major plot, then they can at least do something to make the world a little better. It's Dean retreating back to the safest place he knows: doing what Dad says, because Dad knows best and it's worked out so far, and he's the good son, remember? He knows what his place is.
Sam going through with leaving cracks something, though, and that something's never fully put back together after this. Dean's off-kilter while trying to hunt by himself, and we know that he managed hunting alone just fine before Sam came back into his life. (If nothing else, he lived through enough hunts to make it to the pilot.) Sam's doing okay in his runaway guise, and he's done that before and should be fine, except that he's fine with checking in on Dean, and his thoughts are back in Burkitsville, and even when Meg keeps drawing him toward what his role is meant to be -- independent rebel son -- Sam's tangled back up with Dean, and he isn't willing to throw everything away again to get what he wants.
SAM: You know, if you’re hinting you need my help, just ask.
DEAN: I’m not hinting anything. Actually, uh—I want you to know….I mean, don’t think….
SAM: Yeah. I’m sorry, too.
DEAN: Sam. You were right. You gotta do your own thing. You gotta live your own life.
SAM: Are you serious?
Sam turns back, not long after this. He deflects Meg's encouragement to get further from his 'controlling' family, not long after this. He's softly pleased that Dean still wants to talk to him, and he's shocked by Dean's pride in his independence. The impression we're left with is that Sam just needed to hear it -- that he's not wrong to want to be his own man, to do what he wants instead of following his father's orders. And admitting it does something for Dean, too, that we'll see grow over the next handful of episodes. He envies Sam's independence, even if he struggles to embody it himself. There are things he wishes he'd done or said, or been, that he can't ever be. With a few more truths out in the open, the Winchester brothers grow even closer, and it's that interlocked trust that will lead inexorably to some choices they make in the finale.