" think that it became very uncomfortable to acknowledge that Dean did have a measure of happiness and that the status quo is not something that Dean is currently that happy with
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Well, definetely, to an extend Dean adheres to the idea that he and Sam (and Bobby, and Rufus, and even Ellen back in the day) are birds of a feather - damaged and tainted by the life of hunt. Which is not untrue, given the professional deformation is indeed there. To deny it and to deny *any* affiliation to the hunt (like Sam did at Stanford) would be self-deluding
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Oh, I wish dearly Dean's symmetrical experience not just of Hell, but of post-Hell was brought forth more front and center some time soon. There are scattered implicit mentions hither and thither, but I'd much prefer it came up in the open: it *is* possible to deal with the nastiest aftermath of Hell without any Walls in one's mind. Dean did it and retained his sanity, eventually, though he didn't come out unscathed. I think, this realization would be crucial to move Dean proper on from worrying his wits out over the Wall possibly going down in Sam's mind. Dean's own reference framework of experience may help him let go of the self-appointed 24/7 Wall-duty
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