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The way he asked Naomi "why am I telling you this?" made it sound like he had no free will (sensing a theme?) while in the principal's office, Naruto Shippuden Episode 291 and the fact that he's being forced to spy on the Winchesters without having any memory of it worrying indeed.
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Just as the angels sent an army into Hell to raise Dean from perdition in Season 4, 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. Naruto Shippuden Episode 291 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). 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. 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 (and 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. Naruto Shippuden Episode 291 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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