It was later in the evening when Castiel stood over the sleeping Jack as the Nephilim lay huddled in bed fast asleep. He must have fallen asleep attempting to wait up for him and Caroline. Castiel couldn't help but smile; he was well aware that the evening had been orchestrated by Jack. He took the blankets and draped them over the sleeping Nephilim, tucking him in and brushing a strand of sandy blonde hair out of his eyes.

After a while, Castiel turned around to find Caroline sitting at the edge of the other bed already changed into a long nightgown; her hair brushed out over her shoulders. She smiled as Castiel crept away from Jack, taking care not to wake him. "You're very good with him," she complimented as Castiel settled down into a chair and faced her. Castiel smiled at the compliment.

"Have you and Joe had any children?" he wanted to know. He frowned when she quickly lowered her gaze to look at her hands, her demeanor turning serious. She shook her head.

"It's not something I really wanted," she said softly as he watched her fiddle nervously with her hands in her lap. "But Joe did so we tried. In fact, right before Hannah… but I guess it wasn't meant to be."

Castiel cocked his head, not quite understanding her meaning. His pause caused her to glance up at him, her cerulean eyes meeting his. "I had a miscarriage," she explained. "I don't know whether he resented me or not but… sometimes I wonder. Maybe that's what caused the rift between us… maybe that's why it was so easy to say yes to Hannah."

Castiel sighed. It had never occurred to him to think that this woman's life may not have been ideal before she had encountered Hannah. He had learned about her passion this evening, her love of the past, they'd laughed and shared his memories, but what else was there to know? What else was hidden in the depth?

He got up and relocated to the edge of the bed, sitting down beside her and looking down into her eyes. Studying those deep cerulean orbs, for a moment, he felt almost captivated by them. He cleared his throat. "Why did you say yes?" he wanted to know. "I mean in hindsight, looking back on it, would you still do it?"

Caroline sighed and didn't respond for a long time. She glanced down at her hands again, lips thinning as she searched for the proper response. "Saying yes is easier than saying no," she admitted, not looking up at all. "I guess my life has been one giant yes. Yes to the man my parents wanted me to marry, yes to the career they wanted me to have. You don't draw attention to yourself by saying yes. It's safer. I guess I said one yes too many."

"What about your parents?" Castiel wondered, thinking that it was strange that if Caroline's parents were still alive, why had she been homeless all these years? "They didn't help you out?"
"I'm an embarrassment to them," Caroline explained, turning to look at him now. "I grew up in a small town. Everyone knows everyone, that sort of thing. Reputation is everything to my parents, and I ruined theirs so… I haven't heard from them since I got out of the mental institution."

"Caroline…" Castiel frowned, feeling regret and sympathy. Ironically enough, he knew the feeling well. After all, he'd burned bridges with angels many times, and few thought very highly of him. But they were still his family.

Caroline just shook her head. "It's funny; I dated someone who was more like you in high school. He was independent, free-thinking, lived by his own rules. Everyone in town thought he was a troublemaker. They were convinced he did drugs and if I weren't careful he'd drag me into his life of crime and deviance. So when we got out of high school, and both got accepted to the same out of state university, I had an amazing opportunity. I could study archaeology in Boston while living with the love of my life. But my parents disapproved. They didn't want me leaving Montana, and they threatened to disown me if I went so… I stayed."

"You chose the path of least resistance," Castiel gathered. "And that path was Joe?"

Caroline nodded, shrugging. "It's not that I didn't love him. I did. At least I learned to in time. But he was a safe, secure man. His parents and my parents grew up together. They practically picked him out for me. He's a good man. Or at least he was."

"He seemed to be when I met him," Castiel agreed, remembering how Joe had tracked them down. Caroline only gave him a sad smile and a shrug.

"I can't really blame him for what happened," she said. "After all, who would believe my angel story? And he had to live with the constant judgments from everyone in our little town. I caused the biggest scandal anyone had ever seen. Running off with a man, leaving Joe behind to endure the rumors and the gossip. And when I returned? He was never the same. He was paranoid, distant. He never trusted me again. Until one day, I walked in on him with a woman in our bed. And the rest is history."

"I'm sorry, but that seems cruel of him," Castiel said. That all left an awful taste in his mouth. That Joe would replace her so quickly. It made Castiel glad for what he had. For Sam and Dean. The three of them had literally put one another through hell and had stuck through the worst each of them had to offer.

"As I said, I can't really blame him," she said with another shrug, shoulders slumping in resolution. "It's strange. Having learned a little about angels, their sense of order and hierarchy, I realized I have lived my life like an angel. Always following orders, doing what other people wanted, never what I wanted. I think maybe Hannah chose me for that. She and I had that in common."

"Hannah was a soldier, she knew how to take orders," Castiel agreed. "But she also knew how to give them. And, during her time with me, she also learned when to have the courage to say no, to stand your ground and make your choice whatever the consequences. I had to learn that lesson too not long ago. It wasn't easy, but it's what I learned about being here on Earth. The value of free will. You could have that too, Caroline."

Caroline turned away and quickly shook her head. "No I can't," she said. "I wouldn't know how to begin."

Castiel reached over and took her hand in both of his. Her hand was warm and soft, and Castiel clasped it tightly, waiting for her to turn to look at him. "You can start by telling me what you want," he said. "What do you want right now? Don't think about it, just tell me. Could be anything."

"Well… seeing as how it's past two in the morning, I think I'd like to get some sleep," she said, prompting him to glance over at the digital clock on the nightstand. Her eyes had a slight jovial expression, and he wondered if she was just trying to put a quick end to this conversation. The idea of choosing something for herself seemed to make her very uncomfortable.

"Alright," Castiel acquiesced, giving her an encouraging smile. "But you aren't off the hook so easily. Tomorrow, you are going to make some more choices. And you are going to learn how to say no."

Caroline frowned, looking uncomfortable and nervous. Castiel didn't want to push her into this, but he couldn't bear to see her in this situation. It really broke his heart to hear that this woman once had dreams of her own, perhaps still did, and other people had slowly stripped them all away, and she had let them. And she had gone along with what everyone else wanted, and in the end, it still ruined her life. He had once tried to teach Hannah about choice, about love and 'human things' as she had called them. Now, it felt right to try and teach Caroline the same thing. It was ironic to Castiel that he, the rebel angel, had to teach a human about something he himself had to learn about as an angel.

"It'll be okay, Caroline," Castiel assured her. "We'll start easy. You'll get used to it."

Caroline nodded, and Castiel got up from the bed, moving back to the table to let her get to sleep. He stayed there the rest of the night, watching over both her and Jack, pondering and thinking.

SSSSSSSSSSSSSSSSS

Nick slipped out of the restaurant before Castiel and Caroline's date ended (but not before Jack made some poor excuse to leave them alone). He didn't think he could stand to see more without doing something suicidally stupid. Besides, he had preparations to make. Nick knew he had time. If Castiel had indulged in this little date, he was letting his arrogance and self-assurance get the better of him. They weren't leaving anytime soon. If Nick had been in the seraph's place, he would have snatched Caroline up, willing or no, and hauled ass back to the Bunker, where the Winchesters would be waiting with a library of magical lore and spells and a dozen plus other hunters as backup. Even with the bodies that Nick was leaving behind, Castiel continued to underestimate him. It was infuriating. But so many things about Castiel were.

Before he went back to the warehouse, Nick had to stop for supplies. He usually didn't make the people he kidnapped very comfortable, but Caroline was different. She was special. He wasn't sure what food she liked, so he got a little of everything, provided it would keep. Which meant hundreds of dollars in junk food - chips, cookies, pretzels, soda, peanut butter. Nick even congratulated himself for throwing in granola bars and remembering women's vitamins, since it wasn't likely that Caroline had had good nutrition while she was homeless.

He got good plush, warm blankets, and soft pillows, some crossword books and pencils so she wouldn't get bored if he had to leave her alone. He hadn't been planning on it, but when he saw an early Valentine's Day display, he impulsively bought several heart-shaped boxes of expensive chocolates and two dozen long-stemmed red roses. The gas station attendant had commented that he "must really have the love bug bad."

Nick should have been angry at his familiarity, but instead, he just grinned and said that maybe he did. There was the familiar nervous, restless energy that he always had as he prepared to snatch a victim, but there was something else, too. His palms were sweaty, knees knocking together slightly in his haste. Nick's stomach was awash in a mad fluttering of butterflies. Alright, so maybe the overly-rich food at the restaurant could have something to do with that, but Nick doubted it. He hadn't felt this way in years …. Well, since his first few dates with Sarah. Nick's heart picked up speed a little at the implication.

Nick actually hummed on the drive along the lonely dirt road back to the abandoned warehouse he had commandeered, tapping his fingers on the steering wheel. Nick hummed as he stapled up heavy-duty plastic to cover the drafts of the ancient building. Couldn't have her catching a cold. Nick hummed as he packed up his scalpels, knives, thumbscrews and more exotic implements, and of course, his hammer. It was by far his crudest tool, but effective. It had the weight of history behind it. When his family had been murdered, it had been with this same tool. Nick didn't know why he kept it, except that it was all he had left of his wife and child now. He didn't even have pictures of them, just the object that a demon had used to bash in their skulls and spread their brain matter all over the floor of his home, and how fucked up was that?

But no, now wasn't the time to dwell on past horrors. Nick's plans had changed; he didn't want to torture Caroline anymore. It wouldn't do for her to see his tools as soon as she woke up. That would just scare her, and she wouldn't have the chance to get to know the real him. He'd still have to keep her tied up, of course, to keep her from running back to that lying angel.

It wasn't her fault, not really. Angels were very seductive; Nick knew this intimately. Caroline just needed someone to show her the truth, to help her understand. Once she saw the angel's lies for what they were, Nick was sure that Caroline would understand. She had to. And then she could bring him Jack, and together they could make the Nephilim see that he belonged with Nick, too.

Nick could keep them both safe. Nick could have a family again.

And then he would deal with Castiel.

Nick smiled, a savage, feral grin hungry for blood and darkness, as he absentmindedly stroked his secret weapon, which he had stolen from the Winchester's Bunker when he left: the Book of the Damned.