Over the course of season 4, we've learned a little bit about what happened while he was there.
First, we heard screams and saw images of blood and flame, but Dean denied remembering what he'd been through.
Then we learned that four months in hell is more like 40 years. That hurt, because we can't imagine enduring something for that long (and, of course, it hurts because we love him!). Many fans have wondered why he's not so much more screwed up than he already is, and we wondered that even without knowing what he did for all that time away.
At the end of “Heaven and Hell” (4.10) Dean told Sam that for 30 years, Dean resisted Alistair's pitch for him to step off the torture rack and take over the whip. For 30 years, he was flayed alive, torn to shreds, probably by some of the demons who'd previously taunted him about doing just that. But finally, eventually, he couldn't take it anymore and he stepped down. And he started delivering the torture himself.
Honestly, I could relate. When I was in labor with Number One, I was so freakin' determined not to take ANY drugs. The nurse kept offering them, cajoling me, telling me it was okay to take something, it didn't mean I was weak, etc., etc. Finally, just to shut her up, I agreed. They checked me and I was 8 cm dilated, but before I could say "Wait! I can handle the rest!" they'd injected me with the evil Stadol.
Okay, not exactly the same thing, but still. I can understand how difficult it is to resist someone who won't leave you alone, especially when what they're offering will give you relief from unending pain.
Dean told Sam that he had a giant hole in him, that how he felt was unbearable. Then in “Family Remains” (4.11), he admitted that it wasn't just that he'd tortured souls, or that he'd traded them for himself. It was that he'd liked it. Giving pain eased his, and he reveled in the pleasure of it. I think we pretty much agree that he’s not just referring to the physical pain of being flayed to the bone, but the emotional pain he’s harbored all his life, especially the last few years.
On the surface, his revelation is disturbing. We all want Dean to be heroic and stronger than typical people. We want him to do no wrong, to be able to endure and rise above. Most of all, we want him to not suffer, especially at his own hand.
Since his return, there have been references to Dean being a “dick.” Of course, the fandom was in an uproar over that, but he really is. *ducks rotten tomatoes* Let's look at episode 1.1, "Pilot." Dean breaks into his brother's house, fights him instead of just saying "Hey, it's me," and ogles his girlfriend. He sleeps with truck stop waitresses with questionable rashes, yells at fat kids (and pounds them with dodge balls), steals, cheats, hustles...and, while justified, he spent a lot of time whining about how much he's given up for this family! *foot stomp* He's very much a dick.
Obviously, that's not all Dean is. Those things are all pretty inconsequential in the face of how many lives he's saved and the sacrifices he's made for his brother. It's very easy to overlook them, especially when you love someone like we love him.
Those things don’t make Dean “belong” in hell. But because of them, I don't think his response to hell is out of character.
Have you ever been really, really mad about something, and slammed a door or whipped a hairbrush against the wall? Do you remember how good it felt to lash out, to release the frustration and pain? If the hairbrush broke, or it hit someone walking by the door you just flung the brush through, you probably felt immediately remorseful, maybe even disgusted with yourself.
Dean has had a lifetime of that kind of emotion. He never got over his mother's death, never got what he needed from his dad, never found a home, a place to belong, meaning to his life beyond protecting Sam. Add to that 30 years of being flayed alive, probably mentally and emotionally as well as physically, and yes, it makes absolutely perfect sense that he'd enjoy dishing it out for once. Not to mention that once he stopped at the end of each day, the pain probably returned, ensuring he’d continue his job the next day.
Others, including my brilliant Sisters here, have pointed out that Dean doesn't realize that he wasn't unique. What he was going through was how humans become demons. Hell (in this world) takes the worst of humanity and compresses it, twists it, hardens it until, for the most part, all the good is wrung out. (Ruby and Casey seem to be either exceptions or evidence that the good can still exist, even when overly influenced by the bad--but that's another topic.)
Now Dean's home. He can look at what he did with a "normal" perspective, not from within the rage and pain. He hates it, and has probably latched on to it as yet another reason he's not worthy, to take some responsibility off his shoulders (because it's hard to overcome that self-hate and "become" worthy). He said he didn't care who was in front of him, but now, at least, he has to. He can’t assume they deserved it. He knows better than anyone that some souls don't. Some did deals, some even for noble reasons, and wound up down there anyway.
But whether the people deserved it isn't relevant. The real issue is how much more it punished Dean to deliver torture than to take it. Remember John? Who was in hell for 100 years? I bet Dean has thought about that a lot since he got back, and what his father endured, and maybe at whose hand.
Dean went to hell because he thought his brother was more important than he was. That self-loathing would have festered and been fed while in hell, which is as much, if not more, about internal pain as external. Shredding a person's psyche is essential to turning them into a demon, a creature of evil. Physical pain can be mentally escaped, but not mental pain. So Dean can't look outward and say, "Okay, I was being used, and those people probably deserved it, mostly." He can only look inward and see the horror. That's part of his torture, and I'm sure Alistair takes great pride in the fact that Dean brought it out with him. Part of the insidiousness of hell is that if you escape physically, whether as human or as demon, you house it inside you, perhaps forever.
So what does that mean for Dean? He's afraid his death will send him back to hell. He might even think that being in hell made him deserve to be there, kind of like how people who go to jail often become worse criminals. He's tried to fill the hole in him created by the torture he induced, but after saving the family in “Family Remains” (and failing to save the uncle), decided he never can. He's resigned to being damaged and wounded forever.
A lot of people have said they can't believe Dean can heal from this. That it's too much. And certainly, we know that in real life, there are people who've succumbed to the horrors of war or truly horrendous circumstances, abuse and torture and pain and disgusting things, and turned into horrible things themselves.
But we've also all read about, or maybe even know, people who've gone through hell on earth and not only survived, but gone on to thrive. People who've found meaning and happiness, self-forgiveness and love. I believe it's possible.
On the other hand, people who thrive are removed from whatever they endured. They've found a peaceful place, in some way. In the context of the show, Dean can't ever escape what he knows. Even if he created a cocoon, found a place the evil could never penetrate, he would still know it was out there, would still know there was one less person fighting it. So that peace may not ever be something he can attain without divine intervention.
Who knows which way the writers intend to take it? Even if I weren’t so totally possessed by this show, I’d be in it to the end, just to find out.
I know there are many brilliant points I failed to make here, so please jump into the comments with your own thoughts, disagreements, etc.!