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Now arguably Benny over the years, the kids have to be free to make their own mistakes and learn from them, because boys will be boys. If you love something, let it go, Dean! It will come back to you -- possibly with a dog and a girlfriend or a beard and dirty trenchcoat, but back nonetheless.
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Not that I think Dean should stop attempting to save everyone, of course -- his martyr complex is what makes him a Big Damn Hero, in all his reluctant, Han Solo-esque glory.
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But I do wish that he wouldn't be quite so hard on himself when things are so clearly out of his control, because as much as he's been a surrogate father figure to both Sam and Castiel
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So Dean has issues, as we've established, but Castiel may have bigger issues, since he's currently playing brainwashed sleeper agent for an ominous boss angel called Naomi Amanda Tapping.
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they gave Cas the same treatment in Purgatory, which -- if the angels' original plans for Dean were any indication -- means Castiel is in deep doodoo. The way he asked Naomi "why am I telling you this?"
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But why do the angels want to spy on Sam and Dean, and why does it require Castiel to embed himself with them when angels can lurk out of sight and eavesdrop anyway?
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I suspect it has something to do with closing the gates of Hell, and the possibility that the angels are as opposed to the idea as Crowley is.At some point, it obviously means that Castiel is going to have to do more than just listen and report back.
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Which is particularly heartbreaking, considering the little guy clearly just wants to hang out with his buddies and fight crime/monsters without any more Purgatory drama. These dudes just can't catch a break.

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