what dean winchester truly wanted - a thread.
dean winchester never "wanted" this ending. go back as early as 2x20 where he says: "why is it my job to save these people [and] be some kind of hero? why do we have to sacrifice everything?" does that sound like someone who WANTS to live this life? no, it does not.
when dean says he knows his ending to be "at the edge of a blade or the barrel of a gun" (10x07) he doesn't WANT that to happen. he thinks it might happen due to the hunter's life and he SETTLES for that end. he doesn't WANT it. his fate in 15x20 is not something he ever WANTED.
10x16: a first glimpse about what dean winchester ACTUALLY wants:
dean: "what if i said i didn't want to die... that i wasn't ready."

father delaney: "are you expecting to?"

dean: "the life i live, the work i do i pretty much just figured that's all there was to me, you know?"+
father delaney: "and now?"

dean: "there's things, there's people, feelings that i want to experience differently than i did before, or maybe even the first time [...] i'm just starting to think there's more to it than i thought."
11x04:
sam: "you don't ever want something more?"

dean: "i'm sorry, have you met us? we're batting a whopping zero in domestic life, man."

even after 10x16, he still thinks he can't have anything else than the hunter's life even though he WANTS that "something more"
11x04:
sam: "you don't ever think about something? not marriage. but... something? with a hunter? somebody who understands the life?"

dean deflects the questions and changes the topic. we know he thought about it (10x16) but because of the hunter life he thinks he can't have it.
13x23:
dean: "on a beach somewhere. you, me, cas. toes in the sand, couple of them little umbrella drinks. matching hawaiian shirts."

sam: "you talking about retiring?"

dean: "if i knew the world was safe? hell yeah."

dean thought about getting out. about living a normal life.
in 15x20, dean has a dog and there is a job application on his desk. dean WANTED to get out. he knew the world was safe (refer back to 13x23 where he says if he knew that the world were safe he would retire) and he was planning on living a normal life.
in 15x20 when he claims that this was always going to be his ending it is NOT something he WANTED. he EXPECTED it but he didnt WANT it. dean SETTLED for that ending. he was not at peace when it happened. he was reluctant because "i did not think this would be the day."
in conclusion: no. dean winchester did not want that ending. he never did. he expected it because of the hunter's life. he settled for it because he thought that it was always bound to happen to him eventually. he NEVER ACTUALLY TRULY WANTED that fate.
end of thread.
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