Time frame: Set sometime later in season 4, but before 4.21 WTLB. Spoilers up until 4.21 possible.
Why does he keep going back to her?
Dean stared at the empty bed across the motel room.
At first, it had made sense. Sam really believed Ruby could save Dean's life. She was even helpful, most of the time. She did get the Colt back in working order. But she couldn't stop it. Dean still went to Hell.
She was a dirty liar. Demons lie.
Dean never liked her though. There was always something he couldn't put his finger on, even before she admitted to being a liar.
How come Sam never saw it? Was he really that blinded by her?
He stared at the empty bed. Feelings of guilt crept up out of the silence.
It was my fault. I left him. I started it all by giving her an opening, letting her in. She used me to get to him.
He stared at the empty bed. He bit his lip and felt the anger boil up inside him
I'll kill her. That's what I'll do. If I see her again, I'll fucking tear her lungs out.
Dean stood up, fists clenched. He started pacing. Imagining the ways he would cause her pain.
Then he stopped.
I can't kill her. What will Sam say? What will Sam do? He would blame me.
Dean knew that every time he lost it, fought with her, threatened her, Sam pulled away from him and back to her. It didn't make any sense to him, but he couldn't lose Sammy over it. Where would he be? Where would Sam be?
Dean sat back down.
He stared at the empty bed.
But look what she's done to my Sammy.
Dean pressed his lips together tightly, thinking about how much Sam had changed.
My Sammy would never listen to a demon. My Sammy would not be exorcising demons with his mind. My Sammy is smarter than that, he knows better. My Sammy doesn't need these powers, he's a good hunter. We fought ghosts, and vampires, and werewolves, and demons, all by ourselves. None of this psychic power crap needed.
He stared at the empty bed.
My Sammy wouldn't be fucking hooking up with a fucking demon.
He grabbed a pillow from next to him and squished it in front of him. He had to hurt something. It was either that or he would lose it, and Dean doesn't do that. No tears. Not over that bitch.
What happened to my Sammy?
Dean couldn't even stand thinking about it.
Fuck you Ruby, how are you doing it? What fucking spell did you do to get this tight a hold on my brother?
Dean threw the pillow at the empty bed across from him.
Are you really that stupid, Sammy?
He stared at the empty bed.
It was probably better that Sam was off with her right now. Dean wasn't sure he could look at his brother. Sam was Dean's constant reminder of her. Sam looked different. When she wasn't around, he seemed almost strung out, always nervous about his next move, looking for opportunities to use his power, prove that she was right. Sam had spent so much of his time around Dean trying to justify his relationship with Ruby that they were rarely just brothers anymore.
Well, he tried to justify it for a while.
Now it was mostly just silence. Dean didn't ask. Sam didn't tell. A mutual silence to maintain what civility remained between them.
Things were okay when they were hunting, it was just the rest of the time. Those were the times that were killing him.
When he comes back this time, I'll talk to him. We'll discuss it. He'll listen to me this time.
Dean knew that he was kidding himself. Talking always turned into shouting. Shouting usually ended with Sam leaving again, going back to her. No. Talking wasn't going to work. The best thing he could do was keep Sam with him whenever he could. She stayed away from Dean. Probably the smartest thing she did.
He stared at the empty bed. This time the tears welled up in his eyes, but he willed them to stay put.
I know he doesn't like it. I see the pain in his eyes. He knows it's wrong. How can he not know it's wrong?
Dean realized that he could do nothing. He couldn't stop Sam's pain, either by force or by persuasion, without causing more pain.
I let him go with her, I lose him. I try to split them up, I lose him.
Fuck.
He stared at the empty bed.
A/N: I wrote this while thinking about my best friend's abusive relationship, which I was reminded of by the Rhianna segment on 20/20. That was about the worst year of my life. It seemed to me that Dean went through about the same thing as I did, and that's how this story came about.