okay so I saw this post yesterday and the thoughts would not leave my head so here we are.
The damn lines "Daddy's little girl, he broke" and "just not the man your daddy wanted to be" are sooo tasty to explore.
Like. Obviously we have what we can imagine canon dean is thinking, about how he wasn't strong enough, that he's just so weak and all the guilt of torturing the other people in hell.
but- just consider TRANS dean hearing that line.
Imagine: ftm dean, who has been trying his best his whole life to prove that he is a man.
But-He WAS daddy's little girl. He was, when he was younger, before he realized he was HE. But he doesn't WANT to be anymore. And of course he would feel that him breaking was proof of his inherent un-manliness.
He wasn't strong enough. Truly wasn't the man his dad wanted him to be. John hadn't wanted a daughter (not when a son is so much better on a hunt), but he wanted Dean the way he was (daughter-turned-son) even less. He tried to prove he was a man, to the whole world and especially to John. But when it mattered most, he failed (broke).
and yeah, that's great angst but ALSO consider: mtf dean. And OOOH boy its just as good.
She really is just a little girl inside (deep, deep down), but she's never let anyone know. But Alastair. Of course Alastair knows, and used it against her the whole time in hell, and continues to do so now.
She tried and tried her best to be the manly hunter John raised her to be, but she TRULY couldn't do it (she was just posturing the whole time, it always felt fake). Dean equates her trans-ness as an extension of her own weakness. Thinks her breaking is just another example of how she fails to do what's expected of her, how she is constantly letting people down. Of how she's unworthy. Oof.
thinking again about how one of the fundamentals of dean is how he always feels like he has been living on borrowed time.
Since "In my time of dying", and actually even "Faith", Dean knows that his continued life is directly due to the sacrifice of others. And he hates it.
He was ready to die in 2x01, and as much as he couldn't remember his time as a spirit once he woke up, he felt it. The wrongness of living on.
Sure, Dean doesn't want to die because of it (not yet), but he doesn't feel like he deserves to live. Not with this twice-over extension.
Add his terminally low self-worth from a childhood of "Your Job Is To Protect Sammy" and you get someone who is more than willing to put himself on the line to save just about anyone else.
I get irrationally annoyed when people describe Dean's eyes as emerald. That's not the color-- the closest gemstone color is probably peridot or something.