Okay, here’s what I wish had happened with Dean and Ruby:
remember way back in Malleus Maleficarum, when she saves his life and tells him to stop calling her a bitch? Well, he does. He’s still snide and obnoxious and suspicious, he still swears at her, he still doesn’t trust her much - but he leaves that particular term out of his vocabulary.
Until late s4 - after Heaven and Hell - they’re in a diner, talking a case over during dinner; Sam vanishes outside to call Bobby from the land of cell reception, and inside, Dean snags a few of Ruby’s French fries, because he ordered something that comes with chips, and he wanted some fries, dammit. Ruby, of course, swats at him and snaps “Asshole;” Dean leans back, licks his fingers, and retorts “Bitch” - exactly the way he does with Sam. (Matter of fact, I’d say that happened earlier in the episode, just so it’s fresh in everyone’s minds.)
It’s fresh in Ruby’s mind too, of course, and she’s surprised, spends so long eying him warily that he blinks at her and says “Jesus Christ, fine, have some of my chips, then,” and hands her a fistful. That’s, obviously, not what startled her, but she smiles at him and wolfs the chips anyway.
(This is about the point where Sam returns with news from Bobby.)
There are about a thousand and five other things I want to happen with them, really, because I am a little more invested in this friendship than I can entirely justify - Heaven and Hell is really good to me, in terms of little tentatively friendly moments, but what I would not give for a season full of that - but the other big one, really, well. When the season finale comes around? Dean is still furious, yes, and still furious with her, yes but it’s not because she’s Oh So Evil and Led Sam Wrong. It’s this painful cocktail of hurt and personal betrayal, because he liked her, he’d come to trust her, and seeing her on the other side feels like a direct slap in the face, near as bad as Sammy lying to him.
(Then, in my ideal world, she wouldn’t die, and a slow painful reconciliation arc with a good payoff at the end would start next season. But, if they absolutely freaking had to kill her off - it’s not even deliberate, definitely not Sam holding her down while Dean runs her through. It’s a fight, tangled and desperate and nobody actually wanting to win with a kill, and Sam or Dean stabs her before they can even realize what it is they’re doing, and both of them are more than anything shocked and regretful.)
(But, really, she should’ve lived. She should’ve lived, she should’ve seen what Lucifer really was [see also: this photoset], she should’ve turned on him and then had to face the question: if Lucifer won’t save her people, if the Devil doesn’t want Hell’s children either, whose side is she on? Where’s she stand? She and Dean should have talked down Anna after Michael’s Heaven had her - because oh, how fucking inconsistent can you get? Dean Winchester agreeing to take out Anna after she snaps under torture, when he did the same, when she knew he did the same before anyone but Alastair and still kissed him and told him it wasn’t his fault, when all you have to do is look at him and know that was the world shifting for the better underneath his feet, that moment? Dean Winchester blaming Anna of all people for what she does under the influence of torture? Really?
But that’s a different tangent, and I was saying - Ruby gets to see the fight she’s fighting, Ruby gets to realize that there’s nobody on her side, and she gets to look at Sam and Dean and Anna and say: okay, none of us survive this story that people are telling. There’s no place in this fight for us to win, nobody working for what we want. It looks like we’re on the same side after all, so - let’s try to dodge the whole damn thing together? And Sam and Dean, maybe Dean first, they say yes. Because, well, for all her lies, that crisis of faith they saw at Carthage makes too much sense for them to turn her away.)
