Dysfunctional Shipping Awareness can get way the fuck out of hand.
I get these horrible delusions of coherence about Sam Winchester, so. Bear with me. Or don't, in which case, later. Spoilers through S4 in the post, but anything's fair game in comments. Warning for disturbing content and rampant favoritism. I do as I please.
Sam/Ruby is creepy as hell - and narratively gorgeous - because Ruby knows exactly how to use Sam's whole life against him. Even, especially, the parts of it that we've up until this point been invited to excuse or even idealize. Which means that to scratch the surface of Sam/Ruby, we have to go all the way back to the YED.
I wouldn't classify this relationship as creepy solely because of the apocalypse thing (do you even go here?). What makes this a dark and terrifying relationship is the gaslighting, a particular type psychological manipulation at which the demons excel. The narrower definition of gaslighting is when an abuser attempts to get the victim to doubt his or her perception of reality - things like hiding their keys and convincing the victim they're lost, or denying that a fight ever happened. There's a broader, possibly more colloquial, use of the term "gaslighting" which is more about getting someone to doubt their ability to accurately interpret their own reality - convincing someone that they're objecting to the way they're being treated not because the treatment is objectionable, but because they're dumb, or crazy, or impossible to please. The Winchester saga, I argue, relies on both types of gaslighting.
The paranormal worldbuilding means that the reality-manipulation can go a step past what can happen in real life. The demons could not only make the Winchesters mistrust their ability to comprehend reality, but could materially alter their reality to an extent that's impossible to process. This phenomenon is highlighted whenever we meet a character who can give us a "before and after" on John Winchester, where they describe him as someone who, well, went nuts after Mary kicked it. All this reality-alteration happened before Sam started forming memories - he really does have no idea what normal is.
So the YED messes with reality (ie physical gaslighting) enough to ensure that the humans would do his job for him in terms of the subtler type of gaslighting. Sam spent his formative years in a game of "me or your lyin' eyes" with his father, who kept up as many of the lies as possible until his very dying breath. Sam's discontent with their messed-up lives somehow becomes about how he's just so damn difficult; his aversion to all that danger and violence is about how he's a pussy. I couldn't admire him more for being enough of a stubborn, idealistic bastard to fight back against that at every turn - but that doesn't change how this is the shadowboxing match with self-doubt that he's had indoctrinated into his thought processes.
Enter into this fucked-up perception of a fucked-up world Good Cop Ruby. When she tells Sam about Azazel's violent eradication of everyone who'd ever known Mary Winchester, in that first conversation, she's illustrating and taking her place in the gaslighting campaign. She's telling Sam (and us) about the extent of Azazel's manipulation of his reality. She's showing Sam how much John misrepresented the Winchester family history to Sam, even after Sam's repeated petitioning for the truth, and how (knowingly or not) complicit Dean was in this decades-long deception. And she's - and this is horrifying and brilliant in its truth - setting herself up as the most reliable source of information that Sam is going to get.
This exchange at the end of Sin City exemplifies their dynamic perfectly:
SAM: Maybe I'll just use it [the Colt] on you.
RUBY: Go ahead, if that makes you happy. It's not gonna do much for Dean, though. So, what's it gonna be? (SAM lowers the Colt). That's my boy. This won't be easy, Sam. You're gonna have to do things that go against that gentle nature of yours. There'll be collateral damage...but, it has to be done.
SAM: Well, I don't have to like it.
RUBY: No. You wouldn't be Sam if you did. On the bright side, I'll be there with you. That little fallen angel on your shoulder. (Transcript adapted from SuperWiki)
Particularly, that reference to Sam's "gentle nature" is an amazing move in this whole mind game. It's flat-out untrue: Sam is heavily inclined toward compassion and an aspirational preference for nonviolence, but gentle in practice? Hardly. Ruby, who Sam's only met a couple of times when he is really not at his best, throws it down as a way to establish that she is the one who knows best about Sam's psychological makeup. It accepts the framing that he's been given his whole life - that he doesn't do the things he "should" because there's something innately different about (wrong with) him, and therefore implicitly challenges him to prove that he's not, OR ELSE DEAN WILL DIE BECAUSE YOU FAILED AGAIN, SAM. But she throws him the tiniest bone, in choosing "gentle," with its positive connotations (rather than "weak" as he's been so harshly conditioned to think), and of course he laps it right up, the poor widdle motherless smackhead antichrist giant.
So when Dean does die, Ruby's already set herself up as a familiar, comforting presence. She's everything he knows not only because everyone else is gone, but because she's taken care to become the "everyone else" Sam already had. Ruby functions as a mirror for Dean and a counterpart for Sam in much the same way as Cas comes to function as a mirror for Sam and a counterpart for Dean. Sam's insistence that Ruby's words of wisdom at the beginning of the previous summer are "what Dean would have said" is supposed to make our skin crawl along with Dean's because of Sam's glassy-eyed claim of faith in such an untrustworthy creature. But the real punch to the gut is that it is what Dean would have said - it's practically what Dean did say when trying to talk Sam off the Azazel ledge at the end of S1. Sam's relationship with Ruby functions - or more accurately, doesn't - basically the same way as the whole family dynamic Dean has been so invested in up until now. She keeps him as much in the dark as possible, he fusses about it as much as he can bring himself to while still sticking around because he has no one else to go to, and when she does tip her hand a little he doesn't have the perspective to re-evaluate everything that's come before. And Sam would rather be complicit than have been wrong, he follows her into the dark, even though he knows it means shedding parts of his own humanity.
Ruby, along with the angels and Dean, destabilizes him with yet another impossible dilemma of personal flaws. Instead of being too stubborn/too weak to be a good Winchester, he's now constantly receiving the message that he's too weak/too corrupted by power to fight evil. (Nobody, least of all Sam himself, thinks about his well-being in this whole thing. WHAT IF COMA-GIRL HAD HEPATITIS? SAMMY, I WORRY.) He tips toward Ruby's plan of action for a lot of reasons, but among them is almost certainly the way she offers him at least the illusion of a solution to the perpetual trap of personal failings.
I'm really trying not to set Sam up as some poor victimized woobie without any responsibility or agency in the shit he pulled in the seasons while Ruby's around, because I don't think that at all, not least because I wouldn't be half so sweet on him if he wasn't eminently capable of being a total fuck-up on his own steam. But his emotional entanglement with Ruby is pretty much Sam losing at mind games and getting screwed over. It's creepy as hell. I love it.
Of course, none of this would be half so compelling to me if the dysfunction was entirely one-sided. Ruby is a fascinating character in her own right. For good or bad, her emotional reaction to the whole thing is a bit muddled. I have mixed feelings about the execution of this: she had to remain an ambiguous character in order for the twist at the end to work, and even if she didn't she'd have had to be a convincing double agent anyway, which requires a good deal of mystery. However, I'm very unhappy about the twist, and the deprioritization of Ruby's motives falls into a very disturbing pattern in SPN as a whole to subsume female experiences into male POVs on that experience.
This leaves us a wide range of possible interpretations of Ruby and of Ruby/Sam. This is my favorite interpretation of the relationship: I think Ruby believes, in that twisted demon way, that every word she tells him is true, or at least, as true as she can afford to make it. I think she honest to you-know-who believes she's pushing Sam in the right direction. I think she's sure that he'll be okay with it, when she finally makes him understand. I think she was sure it was all for the best. I think she loved him, as very best as she was able.
Just like John. Just like Dean. Just like Lucifer.
[whole meme below]
Day 1: The ship you don't want to be endgame.
Day 2: The ship you love because it really never will happen.
Day 3: "They are the worst possible thing to happen to each other" ship.
Day 4: The ship that would ruin/assassinate the characters if it happened.
Day 5: The ship where your favourite scene is the most dysfunctional one.
Day 6: The ship where the rest of its fandom is DOING IT WRONG.Day 7: The ship where the writers are DOING IT WRONG.
Day 8: The ship you want to break up so you can stan the hell out of them.
Day 9: The ship you want to see being a trainwreck tragedy because they're too alike.
Day 10: The ship you want to see being a trainwreck tragedy because they're too different.
Day 11: The ship you love for its creepiness.
Day 12: The ship you love for the power difference.
Day 13: The ship you love for the way they hurt each other.
Day 14: The ship you love for the angst, banishing all joy and sunlight.
Day 15: The couple that are at their moral worst when around each other.
Day 16: Most creatively homicidal ship.
Day 17: The ship that looked like a fairytale but isn't or never was.
Day 18: The ship with the most transference issues.
Day 19: The starcrossed ship where the obvious reason they're starcrossed is the least interesting aspect to you.
Day 20: The couple you only ship in an "in another lifetime" sort of way.
Day 21: A couple you ship for the wrong reasons that fits none of these criteria.
Day 22: A couple you ship for the wrong reasons that fits too many of these criteria.
Day 23: A ship you wanted to include but couldn't find the space for.
Day 24: Anything you want.
Day 25: Fanfic and meta that say what you want, but so much more eloquently.
Day 26: Fanvids and fanmixes that say what you want, but so much more eloquently.
Day 27: Picspams, GIFS, and other fandom things that say what you want, so eloquently you feel redundant.
Day 28: The "exception that proves the rule of the rest of the meme" ship.
Sam/Ruby is creepy as hell - and narratively gorgeous - because Ruby knows exactly how to use Sam's whole life against him. Even, especially, the parts of it that we've up until this point been invited to excuse or even idealize. Which means that to scratch the surface of Sam/Ruby, we have to go all the way back to the YED.
I wouldn't classify this relationship as creepy solely because of the apocalypse thing (do you even go here?). What makes this a dark and terrifying relationship is the gaslighting, a particular type psychological manipulation at which the demons excel. The narrower definition of gaslighting is when an abuser attempts to get the victim to doubt his or her perception of reality - things like hiding their keys and convincing the victim they're lost, or denying that a fight ever happened. There's a broader, possibly more colloquial, use of the term "gaslighting" which is more about getting someone to doubt their ability to accurately interpret their own reality - convincing someone that they're objecting to the way they're being treated not because the treatment is objectionable, but because they're dumb, or crazy, or impossible to please. The Winchester saga, I argue, relies on both types of gaslighting.
The paranormal worldbuilding means that the reality-manipulation can go a step past what can happen in real life. The demons could not only make the Winchesters mistrust their ability to comprehend reality, but could materially alter their reality to an extent that's impossible to process. This phenomenon is highlighted whenever we meet a character who can give us a "before and after" on John Winchester, where they describe him as someone who, well, went nuts after Mary kicked it. All this reality-alteration happened before Sam started forming memories - he really does have no idea what normal is.
So the YED messes with reality (ie physical gaslighting) enough to ensure that the humans would do his job for him in terms of the subtler type of gaslighting. Sam spent his formative years in a game of "me or your lyin' eyes" with his father, who kept up as many of the lies as possible until his very dying breath. Sam's discontent with their messed-up lives somehow becomes about how he's just so damn difficult; his aversion to all that danger and violence is about how he's a pussy. I couldn't admire him more for being enough of a stubborn, idealistic bastard to fight back against that at every turn - but that doesn't change how this is the shadowboxing match with self-doubt that he's had indoctrinated into his thought processes.
Enter into this fucked-up perception of a fucked-up world Good Cop Ruby. When she tells Sam about Azazel's violent eradication of everyone who'd ever known Mary Winchester, in that first conversation, she's illustrating and taking her place in the gaslighting campaign. She's telling Sam (and us) about the extent of Azazel's manipulation of his reality. She's showing Sam how much John misrepresented the Winchester family history to Sam, even after Sam's repeated petitioning for the truth, and how (knowingly or not) complicit Dean was in this decades-long deception. And she's - and this is horrifying and brilliant in its truth - setting herself up as the most reliable source of information that Sam is going to get.
This exchange at the end of Sin City exemplifies their dynamic perfectly:
SAM: Maybe I'll just use it [the Colt] on you.
RUBY: Go ahead, if that makes you happy. It's not gonna do much for Dean, though. So, what's it gonna be? (SAM lowers the Colt). That's my boy. This won't be easy, Sam. You're gonna have to do things that go against that gentle nature of yours. There'll be collateral damage...but, it has to be done.
SAM: Well, I don't have to like it.
RUBY: No. You wouldn't be Sam if you did. On the bright side, I'll be there with you. That little fallen angel on your shoulder. (Transcript adapted from SuperWiki)
Particularly, that reference to Sam's "gentle nature" is an amazing move in this whole mind game. It's flat-out untrue: Sam is heavily inclined toward compassion and an aspirational preference for nonviolence, but gentle in practice? Hardly. Ruby, who Sam's only met a couple of times when he is really not at his best, throws it down as a way to establish that she is the one who knows best about Sam's psychological makeup. It accepts the framing that he's been given his whole life - that he doesn't do the things he "should" because there's something innately different about (wrong with) him, and therefore implicitly challenges him to prove that he's not, OR ELSE DEAN WILL DIE BECAUSE YOU FAILED AGAIN, SAM. But she throws him the tiniest bone, in choosing "gentle," with its positive connotations (rather than "weak" as he's been so harshly conditioned to think), and of course he laps it right up, the poor widdle motherless smackhead antichrist giant.
So when Dean does die, Ruby's already set herself up as a familiar, comforting presence. She's everything he knows not only because everyone else is gone, but because she's taken care to become the "everyone else" Sam already had. Ruby functions as a mirror for Dean and a counterpart for Sam in much the same way as Cas comes to function as a mirror for Sam and a counterpart for Dean. Sam's insistence that Ruby's words of wisdom at the beginning of the previous summer are "what Dean would have said" is supposed to make our skin crawl along with Dean's because of Sam's glassy-eyed claim of faith in such an untrustworthy creature. But the real punch to the gut is that it is what Dean would have said - it's practically what Dean did say when trying to talk Sam off the Azazel ledge at the end of S1. Sam's relationship with Ruby functions - or more accurately, doesn't - basically the same way as the whole family dynamic Dean has been so invested in up until now. She keeps him as much in the dark as possible, he fusses about it as much as he can bring himself to while still sticking around because he has no one else to go to, and when she does tip her hand a little he doesn't have the perspective to re-evaluate everything that's come before. And Sam would rather be complicit than have been wrong, he follows her into the dark, even though he knows it means shedding parts of his own humanity.
Ruby, along with the angels and Dean, destabilizes him with yet another impossible dilemma of personal flaws. Instead of being too stubborn/too weak to be a good Winchester, he's now constantly receiving the message that he's too weak/too corrupted by power to fight evil. (Nobody, least of all Sam himself, thinks about his well-being in this whole thing. WHAT IF COMA-GIRL HAD HEPATITIS? SAMMY, I WORRY.) He tips toward Ruby's plan of action for a lot of reasons, but among them is almost certainly the way she offers him at least the illusion of a solution to the perpetual trap of personal failings.
I'm really trying not to set Sam up as some poor victimized woobie without any responsibility or agency in the shit he pulled in the seasons while Ruby's around, because I don't think that at all, not least because I wouldn't be half so sweet on him if he wasn't eminently capable of being a total fuck-up on his own steam. But his emotional entanglement with Ruby is pretty much Sam losing at mind games and getting screwed over. It's creepy as hell. I love it.
Of course, none of this would be half so compelling to me if the dysfunction was entirely one-sided. Ruby is a fascinating character in her own right. For good or bad, her emotional reaction to the whole thing is a bit muddled. I have mixed feelings about the execution of this: she had to remain an ambiguous character in order for the twist at the end to work, and even if she didn't she'd have had to be a convincing double agent anyway, which requires a good deal of mystery. However, I'm very unhappy about the twist, and the deprioritization of Ruby's motives falls into a very disturbing pattern in SPN as a whole to subsume female experiences into male POVs on that experience.
This leaves us a wide range of possible interpretations of Ruby and of Ruby/Sam. This is my favorite interpretation of the relationship: I think Ruby believes, in that twisted demon way, that every word she tells him is true, or at least, as true as she can afford to make it. I think she honest to you-know-who believes she's pushing Sam in the right direction. I think she's sure that he'll be okay with it, when she finally makes him understand. I think she was sure it was all for the best. I think she loved him, as very best as she was able.
Just like John. Just like Dean. Just like Lucifer.
[whole meme below]
Day 1: The ship you don't want to be endgame.
Day 2: The ship you love because it really never will happen.
Day 3: "They are the worst possible thing to happen to each other" ship.
Day 4: The ship that would ruin/assassinate the characters if it happened.
Day 5: The ship where your favourite scene is the most dysfunctional one.
Day 6: The ship where the rest of its fandom is DOING IT WRONG.Day 7: The ship where the writers are DOING IT WRONG.
Day 8: The ship you want to break up so you can stan the hell out of them.
Day 9: The ship you want to see being a trainwreck tragedy because they're too alike.
Day 10: The ship you want to see being a trainwreck tragedy because they're too different.
Day 11: The ship you love for its creepiness.
Day 12: The ship you love for the power difference.
Day 13: The ship you love for the way they hurt each other.
Day 14: The ship you love for the angst, banishing all joy and sunlight.
Day 15: The couple that are at their moral worst when around each other.
Day 16: Most creatively homicidal ship.
Day 17: The ship that looked like a fairytale but isn't or never was.
Day 18: The ship with the most transference issues.
Day 19: The starcrossed ship where the obvious reason they're starcrossed is the least interesting aspect to you.
Day 20: The couple you only ship in an "in another lifetime" sort of way.
Day 21: A couple you ship for the wrong reasons that fits none of these criteria.
Day 22: A couple you ship for the wrong reasons that fits too many of these criteria.
Day 23: A ship you wanted to include but couldn't find the space for.
Day 24: Anything you want.
Day 25: Fanfic and meta that say what you want, but so much more eloquently.
Day 26: Fanvids and fanmixes that say what you want, but so much more eloquently.
Day 27: Picspams, GIFS, and other fandom things that say what you want, so eloquently you feel redundant.
Day 28: The "exception that proves the rule of the rest of the meme" ship.