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"This episode is one of the saddest ones in the series, I think. Dean is just so dead inside, so remote. Contrasting that with who he is in season one? It's kind of terrifying. And he should have won an Emmy for that performance." 4x16 On the Head of a Pin
[SET OF GIFS] 4x16 Whether or not u ship them romantically, there has been a bond between them different then any other relationship that Dean has had with anyone else. Right from the beginning Dean leaves his inner self-loathing and insecurities right on the surface for Cas to see, even talks about them. Dean hasn't shared that much of himself to anyone on the show except maybe Sam. But still he never shows Sam this side of himself because he's always posturing as the strong older brother.
"Oh, just not the man your daddy wanted you to be, huh Dean?" ||| Supernatural 4x16 "On the Head of a Pin"