Sam and Ruby

Sam and Ruby's relationship was one of the most complex relationships in the series. They were initially allies againist Lilith, although Sam never fully trusted her at first.

Sam began to trust Ruby midway into Season Three. Following Dean's going to hell, their relationship took a big leap foward as they "fell in love." Ruby was also Sam's drug dealer as well, since she was entirely responsible for his demon blood addiction. She was ultimately killed at the hands of both brothers.

Background
Ruby did know about Sam before they met. She knew he was the last surviving special child that Azazel had plans for. Before they meet face to face, Ruby watched Sam from afar. Sam did notice Ruby following him though. But when he turned around she would vanish. They finally do meet when Sam is overwhelmed by three demons at once, and she steps in.

Season 3
"Who the hell are you?" "I'm the girl that just saved your ass"

- Sam and Ruby

Sam and Ruby meet when Sam is about to be killed by a demon. She comes up and kills them all using her special knife. Sam had recognized her as the girl following him eariler, and wondered who the hell she was.

After that, she pops in on Sam in a dinner and starts eating some of his french fries. Sam asks about her knife, but Ruby doesn't tell him much other than it comes in handy when tracking down demons. Sam follows up by asking why she is following him. She remarks she likes a tall man and that shes interested in him. The sole survivor of Yellow Eye's special children. She continues on by telling Sam there still is plans out there for Sam, especially after what the yellow-eyed demon did to Mary and her friends. Sam looks confused, so Ruby grabs his hand and tells Sam that he has some work to do and call her when he is done.

Sam calls Ruby later and tells her his discoveries. Ruby tells Sam that Yellow Eyes was covering his tracks. Sam demands her to tell him who she really and Ruby reveals shes a demon. She also tells Sam she can help with getting Dean out of his deal. In Sin City, Sam threatens Ruby with the colt (which she fixed) when Ruby threatens to take it away. Ruby tells Sam if he kills her, she can't help Dean. She tells Sam to think of her as the little fallen angel on Sam's shoulder when she tells Sam hes going to have to do things that go againist his nature. Before that she and Sam got into an argument about killing two demons (Sam argues it was also two humans as well).

We begin to see later that Sam begins to start trusting Ruby. She and Sam are even talking about things without Dean knowing. We see this in Jus In Bello when she offered a plan that would kill all demons in a 30 miles radius. All they had to do was kill a virgin, which Dean instantly no. Ruby asks Sam, and he hesistants to answer. Sam also knows about Lilith thanks to Ruby's intel, but he didn't tell Dean. When her plan is deined, she leaves saying she doesn't want to watch them lose.

As Dean's time is almost up and they figure out Lilith has Dean's contract, Sam wants to call Ruby for help. Which he does despite Dean's wishes. Sam asks Ruby if she knew Lilith had Dean's contract, and she answers yes. Sam asks why she disn't tell him, and she reponds that Sam wasn't ready. Ruby continues on by saying, "If I told you, you too yahoos would’ve just charged after her half-cocked. And Lillith would’ve peeled the meat from your pretty pretty faces." Sam resorts that their ready now. Ruby tells Sam she knows how to save Dean, but its not her, but Sam. Sam is confused, Ruby tells Sam its the powers Azazel gave him and Sam can use them to wipe Lilith off the map. Sam doesn't believe her.

Ruby talks about how Sam doesn't like the idea of being different. She tells Sam to suck it up and learn. Ruby finishes by saying that Sam can save his brother and she can show him. Then Dean comes and traps her in a devil's trap (and grabs her knife). In the end Sam chooses Dean over Ruby. But he does show concern for Ruby as they're gettting ready. Ruby does manage to escape and attacks Dean, but Sam stops her by putting the knife to her neck. When it hits midnight, Sam despertly asks Ruby to teach how to save Dean. But its too late.

Season 4
"You didn't need the feather to fly. You had it in you the whole time, Dumbo!"

- Ruby to Sam

Ruby saves Sam's life when Sam no longer has the will to live. When Sam questions where Ruby grabbed the body, and then tells her to get out, he has no use for her. So Ruby goes and grabs a brain dead patient (there isn't a soul in the body) as her new body for Sam. When she brings up the pyshic stuff again, Sam agrees. Thus, Ruby begins to teach Sam how to use his powers, but Sam couldn't get it right and Ruby kills the demon for taunting Sam.

After burying the body, Ruby confronts Sam and kisses him. Sam draws back quickly and asks Ruby what shes doing. Sam is resisting the tempation because he doesn't want to sink so low as to sleep with a demon. Ruby assures Sam its just her in the body and seduces him. Sam succumbed, and they made love.

Then Sam hears Lilith is in town and goes after her. Ruby tries to stop Sam, but Sam pulls the knife on her and leaves. When Sam gets overwhelmed, Ruby comes and saves Sam. Sam returns the favour and is able to excercise his first demon with his mind. It is believed around this time Sam started to drink demon blood.

When Dean shows up at Sam's door, Ruby pretends not to know Dean. Sam plays along, and pretends not to know Ruby. Like a random hook up. When Sam goes to investigate the diner, Ruby meets up with him, commenting on his progress. Sam asks Ruby what the hell is going on, and Ruby answers she doesn't know. Sam tells Ruby they think a high level demon pulled Dean out, but Ruby shoots this theory down. Ruby asks Sam if hes gonna tell Dean about what they're doing and if they don't tell Dean, hes gonna be pissed. Sam responds that Dean didn't like this psyhic stuff and would try and stop him. Ruby tells Sam that she is not on Dean's good side, and is not going to come between them. Sam says that he doesn't even know what hes doing is right or if he trusts Ruby or not. But he wants to continue.

Later on Ruby approaches Sam about Dean being rescued by angels. When Sam confirms it, she attempts to leave. Sam asks whats wrong and Ruby replies that angels wouldn't care that shes helping, they would still kill her. She continues by saying that the angels scare her and tells Sam to be careful. Sam responds by saying he is not scared of angels. Then Dean finds out what Sam's doing (Metamorphosis) and Sam stops Dean from attacking Ruby.

In I Know What You Did Last Summer, Sam drops everything when he sees Ruby. She gives Sam a tip about a girl the demons what. When they locate the girl, Ruby comes in telling them demons followed them, and then the demons attack. Ruby takes Anna for her own safetly. Sam tells Dean why he trusts Ruby (story is above) and then Ruby comes in to tell Sem where she is. In Heaven and Hell, Ruby helps Sam in his plan to bring the angels and demons together.

In Criss Angel Is A Douchebag, Ruby comes to Sam's room, not too happy. She accuses Sam of wasting time because now, thirty-four of the seals have been broken. Sam counters that he doesn't know what the seals are or how many are there. Ruby suggests that Sam go after the source of all their problems: Lilith. Sam mentions to Ruby that its not the psyhic thing he has a problem. Ruby responds she knows what he has a problem with, but tough. She continues on by saying that Sam should just admit he likes it. Sam plays dumb and Ruby get angry and leaves. Though Sam calls Ruby and starts up again.

It is revealed in On The Head Of A Pin what Sam didn't like to do, but did it anyways. After locating his brother, Sam tells Ruby he needs more, and she tells Sam he can have it. Demon Blood is the reason why Sam's abilities were growing. Ruby is slowly making Sam a demon blood addict, Sam just doesn't know yet.

Then Sam gets locked in the panic room by Dean, but eventually escapes. When he sees Ruby again, he yells at her for not answers his calls. Ruby responds by saying that she can't answer when she on the hunt for Lilith. Then Ruby lets Sam feed while she silently smiles (that should have given Sam a clue). Ruby tells Sam his appetie has gotten bigger and she can't supply him another. She follows up by saying she has a lead on demon whose close to Lilith. Then Dean shows up and tries to kill Ruby, but Sam stops him. In this moment, Sam chooses Ruby over Dean.

So in Lucifer Rising, they kidnap and torture the demon for information on Lilith's location. Then Ruby tells Sam, that they are going to need to bleed the demon dry so Sam can have enough power. Sam is not so sure about it and is even more sure when the demon lets the human out. Ruby isn't too happy the demon did this (she knows Sam is still soft hearted and dislikes hurting innocent people). After a fake message from Dean, Sam agrees to do it Ruby's way. Then she and Sam head into the chuch where Lilith is. Once Sam kills Lilith, Ruby reveals that she was working for Lilith all along and tricked Sam into breaking the final seal.

Now knowing her betrayal, Sam attempts to use his power on her, but is drained. When Dean arrives on the scene, Sam helps him kill Ruby.

Alternative Reality
When Sam and Dean are thrown into the lives of Jared and Jensen. Sam discovers hes married to Ruby. Well, Genevieve Cortese, the actress who plays Ruby. After she returns from a charity event, Sam asks her about any supernatural events that has happened. She answers, Ya, on your tv show. Geneviene comes to the conclusion that Jared (Sam) has been "Sam" for too long. She grabs his hand and takes him upstairs.

Trivia

 * Jared Padalecki said in a convention that Sam believes himself in love with Ruby.
 * Genevieve Cortese, who played Ruby in Season 4, is married to Jared Padalecki (Sam) in real life. She later appears in The French Mistake as herself.