OMG. I need so much more of Stanford!Dean. I would have said it was the only thing Dean couldn't do: give up hunting. But I'm sold that giving up Sam was an equally impossible choice.
We never get to see them at the time so it's hard to judge their state of mind and relationship but isn't Sam the first person Dean is entrusted to save? And the one he saves again and again, even if they weren't soulmates, even if they were just close siblings... Dean is a pseudo-parent. And Sam is just 18, for Dean he's probably still a kid. Having teenager sisters of my own I'd imagine that the constant rejection (and Stanford is a huge kick) is what wore Dean down and disuaded him from his instinctive need to protect Sammy above all else and the implication of Sam choosing normal is that he is not choosing Dean, as part of the SPN world. If Sam asked that would surely tip the scale, I would have a hard time imagining what would compel Sam to ask, personally (but maybe the idea of Sam as super proud it's from Dean's POV, and in reality he simply fought with John and went do what he wanted, and it was quite a mature decision to stop being unhappy). Maybe if he thought it was the only way to save Dean from The Life he would feel it
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