South Bend, Indiana, January 2008


She watched him from the shadows, standing in the parking lot. Saw him draw in a deep breath, and let it out, and knew what he was thinking. Fresh air. Free air. You can't breathe in enough to last you for eternity, she thought.

The lights flickered and went out, flickered again and came back on, he turned toward her and she knew he'd seen her, standing there. He walked toward her slowly, a little wary, a little puzzled, a lot confused.

"So the devil may care after all, is that what I'm supposed to believe?" He stopped on the concrete walkway, looking at her.

Dean Winchester.

She'd been watching them both for a while now. Dean was the key to Sam. And Sam was the key to Dean. And Dean would be a tough nut to crack. Unlike his younger brother, Dean had a wide streak of suspicion, running right through him. Trust had to be earned with him, it was never just given.

"I don't believe in the devil," Ruby said lightly.

"Wacky night." He walked down the steps toward her, and she could feel his paranoia, rising off him like fog off a river. "So let me get this straight, you were human once, you died, you went to Hell, you became a ..."

"Yeah."

She turned away and started walking, listening for him behind her.

"How long ago?"

She took another step and stopped, knowing that he was at least half-way hooked now. The thing with Dean was that under the growling, scowling exterior, there was another man. A man of unimaginable depths, who had no idea as to who he really was. He'd spent too many years trying to become someone else to know. He felt everything, and he felt it deeply. He saw things, connected things, sensed things but had no framework to set those insights to work. And he was afraid of what he could feel, when it didn't relate to getting the job done.

"Back when the plague was big."

Dean walked slowly toward her. She could hear the scrape of the asphalt under his boots, the rustle of his clothing, getting closer.

"So all of 'em, every damn demon, they were all human once?" he said it as if he were just checking the facts, but she knew he was stalling, for time, time to think about it, time to relate to it.

Ruby turned, softening her voice. "Every one I've ever met."

"Well, they sure don't act like it."

He didn't like talking to her, she knew. He didn't like demons, period. And he couldn't understand what had motivated her to save his life, not just this time either, but all the other times as well. And he really didn't like that, not knowing why she did what she did for them. The obvious explanation just wasn't flying to this man. It wasn't rational and it wasn't logical, and he wasn't either. She needed to meet him on an emotional level.

She looked up at him, knowing that this time, this moment, was the critical one. If she could get him to believe her, get him to – well, not trust her, because that was an impossibility for him – understand that she had goals that aligned with theirs, he would be her most important ally with Sam. "Most of them have forgotten what it means, or even that they were. That's what happens when you go to Hell, Dean. That's what Hell is. Forgetting what you were."

He looked away, and she could see that at least half of him believed, despite the rolled eyes, the derisive expression. For the first time, perhaps, he was letting himself think about it.

"Philosophy lesson from the demon, I'll pass, thanks." He retreated back into that smart-ass mode that had protected him to this point from the thoughts of things he didn't like.

"It's not philosophy. It's not a metaphor." She stared into his eyes, watching the words sink into him, watching him take it in. "There's a real fire in the pit, agonies you can't even imagine."

He was listening, when she was talking. The cocky attitude was still there. "No, I saw Hellraiser, I get the gist."

She turned away again, walking a few more steps. "Actually they got that pretty close, except for all the custom leather."

Behind her, he stood still and she walked a little further, then stopped, turning back to him. His face was no longer shuttered, everything hidden. She saw fear and as if he felt that, he looked up at her, the wariness immediately returning.

"The answer is yes by the way."

"I'm sorry?"

"Yes, the same thing will happen to you." She watched that cocky expression vanish, his eyes narrow. "It might take centuries, but sooner or later Hell will burn away your humanity. Every hellbound soul, every one, turns into something else." He was listening now, and thinking. "Turns you into us, so yeah – yeah, you can count on it."

Dean looked away, his mouth lifting at one corner, as he finally asked the question that he needed the answer to, and already knew. "There's no way of saving me from the pit, is there?"

Ruby looked at him. He still had hope, she saw. Not much hope but there was still a flicker left in him. He appreciated honesty, and he already feared the worst. It was a risk but a calculated one.

"No."

He nodded, and she watched the tiny hope disappear from him, his eyes cutting away as he walked toward her again. "Then why'd you tell Sam you could?"

"So he would talk to me. You Winchesters can be pretty bigoted. I needed something to help him get past the –"

"The demon thing?" His brows drew together, pushing the disappointment down, pushing it aside. She watched him do it. "It's pretty hard to get past."

She smiled, at the change in his voice, in his expression, the suspicion back. "Look at you." Big brother, she thought, protective, tough, trying to get intel for his brother. And underneath that, a spreading fear. "Trying to be all stoic. My god, it's heartbreaking."

Dean's gaze cut away, she could see the irritation at her words, the not-so-subtle patronisation bringing him back to the conversation, back to where she needed him to be.

"Why are you telling me all this?"

"I need your help," Ruby said quietly.

"Help with what?" he snapped at her. It was amazing, she thought, he could sense the trap, no matter how well hidden it was. The only way to blunt those instincts was to confuse them.

"With Sam."

He exhaled sharply, turning away and back to her, his expression cold and hard as his suspicions were confirmed.

She gave him a minute to think he had it all figured out, then she continued, "The way you stuck that demon tonight, it was pretty tough. Sam's almost there, but not quite, you need to help me get him ready." She paused, watching his eyes. "For life without you; to fight this war on his own."

And there it was. That realisation of what she was talking about. No big brother around to protect Sam. No one to watch his back. No one to turn to if the fight got too big for him. Alone.

Sometime, she thought, he would also think about the other side of that equation. Where he'd be. What that might be like. How it would feel. But for the moment, it was enough that he realised what life would be like for Sam. Without him.

She turned away, walking steadily away from him, leaving him to think it through.

"Ruby."

She stopped, her back to him and waited. He'd come to the right conclusion more quickly than she'd thought he would.

"Why do you want us to win?"

She turned back to him slowly. The next part was the hardest, harder than dropping the baited hook, harder than letting him play with it. He needed to have a reason to believe her. And it needed to be an emotional reason, one that he could feel, without having to think about it. He was a fascinating man, really. Contradictions piled on contradictions. He could be hard. But the man he didn't know, the one he'd repressed, was strong, rather than hard. And sensitive. And possessed of an extraordinary imagination. It would all work against him, when he went downstairs, she knew. It would tear him apart and they would drink his pain.

"Isn't it obvious?" She looked away, brows drawing together as if the realisations were new and immediate. "I'm not like them, I- I don't know why, I wish I was, but I'm not." She drew in a deep breath and looked back at him. "I remember what it's like."

"What what's like?"

"Being human."

She watched his face change, the compassion that was always there, even when he did his best to hide it, surfacing.

The difference for Dean between a monster and a human, it was a wide gap. Most monsters had started out human, but it was still a card that could work with him.

As you are now, so once was I, as I am now so shall you be. She'd been human. He would become a demon. She thought it was enough.