When you really think about it, the only person who really knows what Dean went through in hell is Chuck. And if you argue that chuck is God, then ouch, because that’s Dod looking at Dean like that. He looks so guilty and haunted. He made one of his own creations be tortured, and made him torture too, and all because it was written, when it didn’t have to be
You guys are picturing happy things but im sitting here imagining Dean after his mom dies. His Dad drinking more, almost always out, and him alone with Sammy. Him slowly realizing that the Easter Bunny and Santa isn't real. The tooth fairy not giving him a new quarter. So he vows to give Sammy something to believe in, and as long as possible, before the monsters and the dark catch up to him.
Journal of A Man of Letters | Sam Winchester's Journal - Entry #47 ||| "My brother has never borne the thought of loneliness. It has always terrified him more than death, more than Hell, more than anything. That’s why he showed up at Stanford when Dad vanished or why he went to Lisa after I fell down the Pit. That’s why he saved my life so many times, consequences be damned." [...] READ THIS!! IT'S BALLS-ON ACCURATE!
Journal of A Man of Letters | Sam Winchester's Journal - Entry #46 ||| "And now there’s this…thing on his arm, the Mark of Cain. I can’t believe how detached, how calm Dean was when he showed me the scar. Telling me about his cool brand new tattoo or about a pair of jeans he bought this morning would have been exactly the same. ... Now I have to try everything so that my brother can do the right things too. It is my turn to be his Jiminy Cricket." [...]