First: a warm welcome to everyone who has joined the community. I'm looking forward to some great discussions. If you have any old posts of interest to the community, please feel free to post links here.
To kick things off, here are my thoughts about the Sam/Ruby relationship so far in season four: specifically, whether their relationship is sexual and what that implies.
The scene in Sam's hotel room is certainly ambiguous. I wasn't certain even after a second viewing that Kristy was the same actress as played Ruby at the end of the episode. I had to check the cast, and she is. But that still leaves questions:
Was Sam sleeping with Kristy? It's the obvious conclusion considering she answered the door in her underwear, and Sam's conversation with Dean appeared to confirm it. But if Sam was lying, that wouldn't be the only lie he told Dean. It would make sense for him to lie, give Dean a story he would accept, rather than reveal that he and Ruby have become whatever they are. It's worth noting that Sam wasn't undressed...then again, maybe before he came into view he was hastily getting some clothes on. We can't know for sure.
While there's a case for interpreting the scene as non-sexual, I think the alternative has a stronger case. If it looks like a duck and quacks like a duck, chances are it's a duck. If Kristy were the human girl she appeared to be, there'd be no question, because what the hell else would she have been doing in Sam's room, half-dressed and waiting for pizza. In a symbolic sense, the pizza is code for "they've just had sex" - in the same way lighting a cigarette was used to create a post-coital mood in movies before smoking became unfashionable. Taken at face value, this was a very casual one night stand: I guess given the shock of seeing Dean Sam can be forgiven for forgetting her name, but that's a telling moment. She's not someone he cares about at all, just someone he's had sex with.
Was Kristy possessed by Ruby in that scene? On the one hand, you'd think Ruby would show more of a reaction to seeing Dean back from the dead. This seems to be the strongest piece of evidence in the case for Ruby not being in her body in the motel. That said, we still don't really know what Sam and Ruby were doing in town and I suspect it's at least possible that Ruby already knew Dean was back. The other demons appeared to know. If so, she hadn't told Sam...but it wouldn't be the first time she's kept something important from him.
If it was her, Ruby's a pretty good actress and Sam's damn good at improv - but then, we know that's true of both of them. A demon must be good at acting, just to impersonate humanity most of the time, and Sam's job as a hunter calls for the ability to improvise a convincing story, fast.
The next time we see her is in the diner, and there she is immediately recognised by Sam as Ruby. He shows no reaction to Ruby's choice of body; and if this was a girl he'd slept with (even if he felt nothing for her) I would expect to see some reaction. So I'm pretty confident that Ruby was in that body when we first saw her and that Sam knew it.
Which brings me right back to the original question: was Sam sleeping with her? There's a lie in the motel scene whichever way we slice it. If I assume Ruby being in Sam's motel room wasn't sexual (they're just sharing a room, much as Sam and Dean always did), then presenting it as a casual sexual encounter might well have been the lesser evil from Sam's point of view. Better for Dean to assume Sam's sleeping around - hardly a lifestyle Dean's in a position to criticise - than for him to know how close (emotionally) Sam has become to a demon.
Personally, I suspect the scene was exactly what it looked like, and they were having sex not long before Dean knocked on Sam's door, though I do think there's enough ambiguity in the situation to make either interpretation valid.
And here's where I get to the real point: what does this say about Sam?
It's not about his choice of sex partners. Whatever he's doing with Ruby is likely consensual.
But what about the girl whose body Ruby has hijacked? It's rape. There is no other word for it*. Sam, who has experienced possession himself, knows it. While he was possessed he was forced to do some terrible things, including the implied rape of Jo. Does he not care any more?
More to the point, is the viewer not supposed to care?
The motel scene serves several narrative purposes: primarily to reunite Sam and Dean with a cute little shout-out to the Wincest fans (very nice). But another important purpose of the scene is to provide a snapshot of how much Sam has changed while Dean's been away. The casual sexual encounter, even before we know the girl is Ruby, does that very neatly, because casual sex is so out of character for Sam. We are supposed to see him as a changed man, maybe even as a broken man.
But the episode makes no attempt to judge Sam for rape. He is implicitly judged for his other actions: for working with Ruby, for lying to his brother, perhaps even for his super-psychic-exorcism. The way these things are presented onscreen makes it clear we're supposed to think of Sam as in the wrong: he's flirting with the dark side, doing the demon's bidding.
His implied rape of the girl Ruby is possessing is damn near played for laughs. The sole comment on it is Sam's line when he says she's not a prostitute, or words to that effect:
DEAN: So tell me, what'd it cost?
SAM: The girl? I don't pay, Dean.
The whole issue is simply dismissed. Neither of the brothers see anything problematic in it. The girl is barely even a person until she's revealed as Ruby; she's a device, an object to get a quick laugh out of the audience. IMO, that's the one thing it's never acceptable for a TV show/movie/novel to do: rape is not, under any circumstance, funny.
Honestly, it spoiled what could/should have been an outstanding episode for me. Great start to the season, Kripke.
* Note: Doesn't that make Ruby a rapist, too? Well, yes, but she's a demon. She's meant to be evil and what she does to the bodies she inhabits serves to illustrate that. Sam's supposed to be a hero.