Dean had it drilled into his head at a young age that there was no time for him to be emotional. If he was upset, if he was having a hard time, if he had too much on his plate— oh well, because he has responisbilities. He has a little brother to look after, and monsters to fight off, and a motel room to keep up, and everything in between.
And that became him shell. If his worries and troubles were rain, he was plastic. He just let them slide right off him, because he doesn’t have time to sulk, he doesn’t have time to cry, he doesn’t have time to feel sorry. He always feels like as long as he pretends he’s okay, then everything else will fall into place. For this brother’s sake, for this father’s sake, for the sake of avoiding becoming in-touch with his emotions. He’s learned to want no part of it.
But at the root of it all is his family. He’d do anything, kill anything, say anything to ensure that they feel better. Forget what he’s feeling, he needs to keep his family together. Especially with Sam and John always butting heads; he put it upon himself to step in the middle and literally be the glue to their family.
He has deep-rooted abandonment issues. He thinks everyone’s going to leave him— he’s literally terrified of being alone. It’s his biggest fear. I’m sure he’s been saying it in his head for years: everyone’s going to leave you, you’re going to be alone, you’ll have no one, they don’t need you like you need them.
And that really has him torn. Torn between doing all he can, and not doing anything at all — because he does think that he’s not good enough. He never thinks he’s done enough. He never feels like enough.
And that’s a horrible way to be, because he doesn’t see just how amazing he is. He doesn’t realize that he’s stronger than pretty much anyone. He’s done things that are almost impossible. Not everyone can deal with all the things he’s dealt with; that one everyone can handle suddenly being the guardian of someone, especially at a age where he’s not even old enough to legally be a guardian.
Under the womanizing, and the sarcasm, and the hardened shell— Dean Winchester is a boy, inside the body of a man, who’s looking for answers; looking for love; looking for acceptance; and hoping that he doesn’t blink too soon— because one day all that he loves and lives for could be gone.