I don't own Supernatural or any references to anything else you may recognize.

"You look like you could use a friend," she said kindly, her warm brown eyes crinkling at the corners when she smiled again. "I'm Jillian, but you can call me Jill."

The Apocalypse was over.

Sam Winchester's crazy plan had worked, and now he and his half-brother, Adam, were in the Cage with Lucifer and Michael. Obeying his brother's wish, Dean had gone to live with Lisa Braeden and her son, Ben.

With Michael gone, Heaven was in a state of chaos and anarchy. The archangel Raphael was collecting followers to help him restart the Apocalypse, and no one could or would stand against him.

Except for Castiel.

He had tried to fight against his older brother, but he had been defeated easily, and Raphael hadn't even broken a sweat. Castiel kept up his defiance, and the Civil War in Heaven began, Castiel's few friends and followers against Raphael's infinite numbers. To have even the slightest chance of winning, Castiel would need to gain an unimaginable amount of power. The question was how.

Castiel watched, invisible, as Dean raked up leaves in Lisa Braeden's backyard and put them in a garbage bag. He had been standing there for a very long time, debating whether or not to reveal himself. He needed help, and Dean was the only one he knew to turn to. But Castiel couldn't do it. Dean had sacrificed so much, and Castiel couldn't bear to ask him for more.

"Ah, Castiel. Angel of Thursday. Just not your day, is it?" Castiel turned to stare at the demon Crowley, who had somehow snuck up on him while he was watching Dean.

"What are you doing here?" the angel asked, somewhat accusatorily.

"I want to help you help me help ourselves."

"Speak plain."

"I want to discuss a simple business transaction. That's all." The demon smirked at the disbelief on Castiel's face.

"You want to make a deal?" Castiel said incredulously. "With me? I'm an angel, you ass. I don't have a soul to sell." What was Crowley getting at?

"But that's it, isn't it?" Crowley's smirk continued to grow. "It's all of it. It's the souls. It all comes down to the souls in the end, doesn't it?"

Castiel's patience was growing thin. "What the hell are you talking about?"

"I'm talking about Raphael's head on a pike. I'm talking about happy endings for all of us, with all possible entendres intended. Come on, just a chat."

"I have no interest in talking with you."

"Why not? I'm very interesting. Come on. Hear me out. Five minutes. No obligations. I promise—I'll make it worth your while."

After a moment's hesitation, the angel spared one last glance at Dean and followed the demon.

Castiel was back on the park bench in Chicago, and for what reason, he didn't know. It had been around six months since he met Jillian the prostitute. For all he knew, she could be gone. He hoped desperately that she wasn't.

He just needed someone to talk to. After hearing the terms of Crowley's deal, he had told the demon he would need time to consider. What Crowley was suggesting… it was insane. An angel and a demon, working together? Castiel may not have been very good at understanding humor and sarcasm, but he knew for a fact that, no matter how bizarre the deal was, Crowley had not been joking.

The offer was tempting, to be honest. And it did seem like the only way. But it couldn't be, could it? Hadn't he learned that trusting demons was never a smart thing to do? And shouldn't that mean that an angel would have to be twice as stupid to trust one? If he agreed to Crowley's deal, he would be in league with the King of the Crossroads—no, now that Lucifer was gone, Crowley was the King of Hell, which was infinitely worse.

Castiel folded his hands in his lap and leaned slightly forward, staring out at the small playground across the road from the park bench. It was crawling with small children, all wearing identical purple shirts. He supposed it was for some kind of school outing. He watched the children for a minute, thinking of Jillian's job at the orphanage and wondering if she had earned enough money to quit her other job. He remembered how much she had wanted children.

Why did he care so much? She was just a woman he had met once and never seen again.

No, that was a lie. She had changed his life. Just by saying a few words, she had restored his faith in his father.

True, his father was gone. But He wasn't dead, and He did still care. He brought Castiel back to life when Lucifer had killed him. He had restored Castiel's angelic powers. He had given Castiel a chance to change the hierarchal order of Heaven, to take the power from the archangels and reform the system for the better. No more killing, no more attempts at starting the Apocalypse, just peace—the way it should be.

Castiel sighed. She wasn't there, and she wasn't going to be there. It had been a fleeting hope, and a terribly stupid idea. He scoffed at himself, at how pathetic he was. With a last glance at the playground, he stood up, deciding it was pointless to stay any longer.

Wait. Castiel did a double-take. It couldn't be… Was that really—?

Jillian the prostitute was currently helping a small girl up the ladder to the plastic yellow slide. She looked different somehow, and it wasn't because of the fact that her hair had grown to her elbows and she was wearing more conservative clothes (including one of those purple t-shirts). No, this was something else. She looked happy. When he had met her the first time, she was full of pride and dignity and acceptance of her less than fortunate life, but she hadn't looked truly happy.

That had completely changed. As he watched, she threw her head back and laughed as the little girl slid down the slide and tumbled onto the ground. Even though he was too far away to hear it, he could imagine her loud, boisterous, occasionally snorting laughter, and he felt a small smile spread over his face.

Suddenly, she looked right at him, her smile faltering the slightest bit as she tried to work out who was staring at her; then she grinned widely as she was hit by the realization. She bent down to say something to the little girl, who ran to another woman sitting on a swing and whispered in her ear. The woman nodded at Jillian, and Jillian grinned again, then walked to the curb, waiting on a car to pass. Once the road was clear, Jillian jogged across and came toward Castiel.

He couldn't stop smiling, and he didn't know why. Who was this woman to make him feel so much? He was a full angel now; his human emotions and cravings shouldn't be this strong. But they were.

Jillian didn't stop in front of him; instead, she lunged at him and wrapped him in a tight hug that cut off his flow of oxygen—not that he really needed it. "Cas!" she exclaimed. "What the hell are you doin' here?" Castiel coughed a little, and she released him, stepping back and blushing furiously. "Sorry 'bout that. I just never thought I'd see you again!"

"Hello, Jillian," he said awkwardly, shifting from foot to foot uncomfortably.

"What'd I tell you last time, Cas?" she said, shaking her head. "Call me Jill!"

"Jill." Castiel said her name reverently, liking the way his mouth formed around the word.

"So why're you here, sweetie?" Jill asked.

Castiel hesitated, unsure of what to say. It's not like he could tell her about the deal. It wasn't as simple as talking about his father—all he had to do then was refer to him as "Father," instead of "God," which is what he usually did anyway. But on the other hand, she had somehow figured out that he was an angel, and she didn't question that whatsoever. Maybe he could tell her. He could certainly use her caring advice.

"C'mon, sweetie," she coaxed, reaching for his hand. He stared down at their entwined fingers in bewilderment, and she squeezed his hand. He had forgotten how her touch felt, how right it seemed. "You can tell me."

"How did you know?" he said, finally having made up his mind.

"Know what?"

"That I'm an angel."

"Oh!" Jill looked up at the sky thoughtfully for a minute. "I dunno. I just kinda… knew. I mean, the way you talked about your dad—it sounded like my whole 'faithless' situation. And how you didn't really get the way I was talking, like that you thought I was sayin' your skin was blue and I was gonna give you money for talking to me. And your name, too. You looked all uncomfortable when I asked if you were named after the Angel of Thursday. The pieces just kinda fit, and I just had this feelin'. Guess I was right!"

"Oh." Her confession worried him. If she had pieced it together, what if other humans he had interacted with had, too? Maybe he wasn't as good at blending in as he thought…

"Cas, you're stalling," Jill said, raising an eyebrow expectantly.

"I am?"

"Yeah, and you know it, too. Tell me what's wrong. I know you weren't just passin' through the Windy City. I mean, you're an angel. You gotta have a reason, right?"

Oh, yes, he had a reason. She was the reason—not her kind words and her advice, just her. He had thought about her every day since they had first met, even during the final battle at Stull Cemetery. But he shouldn't say that, should he? No, that would be much too forward and much too pathetic.

Instead, he said, "You gave me good advice once, and I was hoping that you could again. I just don't know who else to turn to."

"Alright, well, I'll try," Jill said, nodding. "But you're gonna have to tell me a little bit of your problem, y'know." She led him over to the park bench and pulled him down beside her. "So… penny for your thoughts, Mr. Thursday?" She smiled brightly, her eyes crinkling at the corners like always, and a grin tugged at the corners of Castiel's mouth.

"It's… difficult to explain," he began, staring down at the ground. Maybe he shouldn't say anything. Maybe he should just leave. He was getting a human involved in the affairs of Heaven. This had to be illegal.

"Give it your best shot," Jill encouraged, squeezing his hand once reassuringly, and all of his determination to leave disappeared. To Hell with the rules. He'd broken enough of them already; one more wouldn't make a difference.

Taking a deep breath, he looked back up at her, fixing her with big, pleading, blue eyes. "There is a civil war in Heaven, between Raphael and his legions and… and me and my few followers." Jill gasped, her grip on his hand tightening slightly. "Maybe… maybe I should go back further," he said unsurely.

"Yeah, that might help," she agreed, her eyes wide with alarm.

This was going to be difficult. "First, you have to know that the Apocalypse has come and gone."

"That can't be true," Jill argued disbelievingly, releasing Castiel's hand to gesture wildly. "Where was all the death and destruction?!"

"It is true," Castiel assured her. "I, along with three hunters, stopped it."

Jill stared at him incredulously; then her eyebrows scrunched together in confusion. "Okay…" she said slowly, seeming to believe him. "Okay. And by hunters, you mean like redneck, backwoods hicks or…?"

"Sam, Dean, and Bobby hunt supernatural creatures…" Castiel informed her hesitantly, wishing he hadn't said anything. He didn't want to scare her and have her live her life knowing what was out there. On the other hand, maybe it was best that she knew. Then she could protect herself.

"Wait, what? You're joking! You gotta be joking!"

"I… I don't really joke, Jillian—uh, Jill."

"Yeah, but… Monsters are real?!"

"I'm afraid so."

Jill let out a small snort of mirthless laughter and shook her head slowly. "Vampires and werewolves and ghosts—oh, my!" she muttered, sounding awed. "So these humans—I mean, guys—hunt monsters for a living?"

"Yes, and there are others out there. They all began hunting for different reasons, most commonly because a loved one was killed by one of the creatures. It often becomes a tradition, passing down through generations. Sam and Dean, for example, were raised in the life by their father after their mother was killed. They recently discovered that she was also a hunter and was also raised in the life." He felt kind of shameful and traitorous for telling a stranger about the Winchesters' lives. Dean would not be happy with him. But Dean wasn't there anymore, and Jillian wasn't really a stranger. At least, not to him.

"Who would do that to a kid?" Jill asked, sounding slightly angry. "That's awful!"

"Is it really?" Castiel replied calmly. "If you knew what was out there, would you not do everything in your power to protect your children from harm? Even if it meant raising them like warriors?"

"Well, when you put it that way…" Jill frowned and looked down, absentmindedly grabbing his hand and flipping it over to trace the lines on his palm. He fidgeted a little at her light touch, and she stopped and looked up at him questioningly.

"D—don't," the angel stuttered nervously. "It—it's nice." And it was, as was everything else that Jill did to him. Every glance, every smile, every touch was just extremely nice.

Jill grinned at him, her brown eyes sparkling mischievously, and her finger resumed its path along his hand. "Do I make you nervous, Cas?" she teased.

"No!" he protested, just a little too quickly, and Jill laughed. He hung his head in embarrassment. "A—a little," he admitted sheepishly.

"It's okay," she assured him. "You make me nervous, too." A small, slightly uncomfortable silence passed, a silence just long enough to allow Castiel to wonder over Jill's confession. Was it really possible that he affected her in the same way that she affected him? "We keep gettin' off topic," Jill said, interrupting his thoughts. "You still haven't told me what's wrong."

Castiel froze. It wasn't too late to turn back. He didn't have to tell her anything. He had already told her about the supernatural and the Apocalypse, he didn't have to involve her in his deal with Crowley, too. No, he didn't have to tell her—but he wanted to. "I was given an offer," he said at last, and Jill looked up at him again. "A demon named Crowley—the new King of Hell, now that Lucifer is back in his Cage—wants to help me win the war."

"A demon?" Jill gasped. "So—so demons are real, too?"

"Unfortunately, yes—they are very real, very manipulative, and very dangerous."

"Yet you're still considering the deal? Even knowing how they are?"

"You don't understand," Castiel said, making a low, frustrated noise in the back of his throat. "Crowley is going to help me get souls—full of raw, absolute power—and I need that power to defeat Raphael. He's much stronger than me. I stand no chance."

"What's so bad about a Teenage Mutant Ninja Angel?" Jill asked curiously, and Castiel gave her an odd look. Dean had called Raphael that, too. He had no idea what either of them was talking about. "I mean, he's an angel; he can't be that bad."

"Lucifer was also an angel," Castiel reminded her.

"Ah. Good point. But, still. What's so bad about him?"

"Raphael is a traditionalist, and he always has been. He also harbors a certain dislike for me and angels like me. We disagree with his ideas."

"What's a traditionalist?"

"A traditionalist is someone who wants to restart the Apocalypse so that it will end in the desired way—Michael and Lucifer, locked in a fierce battle to the death. If Michael wins, Earth becomes Paradise. If Lucifer wins, Earth becomes Hell."

"Why not just help Michael win?" Jill suggested. "Wouldn't that be the logical thing to do?" Oh, how naïve she was. He had thought the same once. But he had learned better.

"That was my original plan," Castiel agreed with a nod.

"But?" Jill asked. "What changed?"

"Two boys and an old drunk taught me that freedom was better than a forced paradise—for that's what Earth would have become had the Apocalypse ended in the angels' favor."

"I dunno… Paradise would be nice…" Jill mused, "…for some people, anyway..." She looked across the road at the playground and returned the cheery wave of the little girl from earlier. Castiel knew that she was talking about herself, and it physically pained him when he thought of what she had been through.

"But what's the price of Paradise?" he responded. "For it to happen, countless people would have to die."

"I guess I get what you're sayin'," she said as she turned back to him. "It's not really Paradise if it has so many casualties, is it?"

"No, it isn't."

"This deal… What are the terms?"

Castiel sighed. Here came the crazy part. "Crowley and I are going to search for Purgatory. With its supply of souls, I'll be nearly invincible. Raphael won't stand a chance."

"And the demon? Crowley?"

"What about him?"

"What does he get out of all this?"

He hesitated. This was the part of the deal that unnerved him. He supposed it was fair, but Crowley gaining power couldn't be a good thing. And he knew that Jill would feel the same. "Half of the souls," he said finally, not meeting her eye.

"Cas, you can't be serious!" Jill exclaimed. "The King of Hell is gonna get his hands on half the souls?!"

"I know. I don't like it, either."

"You can't find Purgatory on your own?" she tried.

"Crowley has resources that I don't," Castiel told her, "and he has time, which makes him infinitely more valuable. I'm in Heaven almost constantly, and when I'm not, I'm keeping an eye on Dean. With his brother gone, I imagine he's yearning to do something stupid, like selling his soul again."

"Selling his…? Again…?" Jill squeaked. Castiel sighed. Why had he mentioned that? "Okay, never mind," she said, shaking her head vehemently. "Forget it. I see where you're comin' from, Cas."

"You do?" Surprise colored his deep voice. How could she be so understanding of everything?

"Yeah, I do. You feel like you got no other choice, or, even if you do, this is the best one."

"Yes, exactly."

"I'm sorry."

Castiel's brow furrowed in confusion. "For what?"

"I don't have any metaphors or some past experience to compare your problems to this time." She grinned apologetically, and he felt himself smile again.

"I… I don't think I expected you to," he admitted. "I just needed to talk to someone." That was almost the truth. He had just needed to talk to her.

Jill laughed. "Well, I'm definitely one for talking." Castiel's smile widened the smallest bit as she snorted. "But I can give you one little piece of advice. It's very cliché, and it might not work for an angel, but I always thought it was the best advice there is."

"What is it?" he asked curiously.

Jill took his hand in both of hers and squeezed it gently. "Close your eyes," she told him. He opened his mouth to protest, but she stopped him, commanding, "Just do it!" He obeyed reluctantly, realizing the reason he'd tried to protest was that he didn't want to take his eyes off her, not even for a millisecond. "Now, empty your mind," she instructed, making her voice mysterious and grand. He knew enough of human culture to know that she was mimicking the women who wrongly called themselves psychics. "Let all your thoughts filter out."

"I don't see how this will—"

"Silence! Obey me!" Jill giggled and Castiel smiled at the sound. "Now, be completely still… and listen." By the end of the sentence, her voice had dropped to an almost-whisper.

"Listen to what?" Castiel whispered back.

"Your heart," Jill said, her voice now just barely audible. "Listen to your heart, Castiel. What's it telling you?"

Castiel listened. At first, there was nothing, and he began to feel quite ridiculous. He listened harder, if only to appease Jill. Then, suddenly, he knew what he had to do. It may not have been the only way, but he felt it was the best way. He would agree to the deal, but Crowley was an "idjit," as Bobby would say, if he thought that he was going to get a single soul. He would have to think that he was getting an even share, though, or he would most definitely call off their arrangement, and Castiel couldn't have that.

Once again, Jillian had helped him in a way that could never be repaid.

He opened his eyes, about to thank Jill for her help, but he froze. Her face was mere centimeters from his, and her chocolate brown eyes bore into his very soul—that is, they would have if he'd had one.

"Cas," she breathed, "would it be a sin to kiss an angel?"

Castiel blinked rapidly, his heart racing at a pace that, for a human, would've indicated cardiac arrest. He swallowed nervously and managed to stutter out, "I—I don't k—know…"

"Guess I'll find out the hard way, then, huh?" Jill closed the distance between them and softly pressed her lips to his.

Castiel didn't know what to do, but he tried his best. He had never shown any affection to anyone, especially not like this. The closest he had come was the night that Anna held his hand and convinced him to consider disobedience.

Well, there was that one time Dean took him to a whorehouse, but that had ended badly…

Jill pulled back finally, a faint blush gracing her tan cheeks. "Sorry," she said quietly, her hand coming up to push a lock of hair behind her ear. Castiel briefly wished he had done it for her. She wouldn't look at him, choosing instead to stare at their still-entwined fingers. "I shouldn't have done that."

"No!" Castiel yelped, his eyes growing wide at the thought that she regretted it. To him, even though he wasn't sure how those things worked, it had been the most wonderful experience of his existence. The soft, inviting warmth of her lips was unlike anything he'd ever felt before. "I… don't know how to… I apologize if it was… unpleasant." The angel hung his head in shame and embarrassment, feeling a blush creep up his neck.

"Oh, that's what it is?" she asked, sounding both surprised and relieved. "I thought you were actin' like that 'cause I broke some law or something by kissing you! Oh, Cas, sweetie, you did fine! Hell, if you practice a little, I bet I could make the next Casanova outta you!"

He didn't understand her reference, but the meaning was clear. He wasn't as awful as he thought he would be. And Jill had nothing to worry about. As far as he knew, kissing an angel wasn't a sin. And if it was, well, they'd have to go through him to get to her.

"So… did you figure out what you're gonna do?" she asked, bringing him back to reality. She seemed to be acting like the kiss had never happened, and he couldn't decide if he was hurt or relieved. He decided on relieved. Knowing Jill, she changed the subject to take his mind off of his insecurities.

"Yes, I did," he told her. "And—"

"I don't wanna know what you chose, okay?" she said, holding up her hand to stop him. "'Cause if you think it's the right choice, then you should go for it, and I don't wanna accidentally influence you to change your mind." He found himself speechless at her level of understanding. "Hey, Cas?" she said hesitantly when he still didn't say anything.

"Yes?"

"What's the real reason you came back? I mean, the advice thing—that's pretty much bull, and you know it. You're not the best liar, sweetie. I guess it kinda comes with the whole 'angel' thing."

The real reason? he wanted to say. The real reason that I came back was to see you again. Since that night, I've thought of almost nothing else but you. Even with the Apocalypse going on, you've been at the forefront of my brain the entire time. I'm an angel of the Lord and a commander in Heaven's civil war—I shouldn't feel like this. When God brought me back, my humanity should have disappeared, but, if anything, it's stronger. That humanity is what made me come back.

But, of course, he couldn't tell her that. Instead, he squeezed her hand hard, knowing that what he was about to say would ruin everything.

"You're a human," he told her, keeping his tone as neutral as possible. "You don't know how to protect yourself from the real danger that inhabits this world. You did me a favor once, and I felt it was my duty as a child of God to return the favor. So I came to make sure that you were safe. If you were to die, it would weigh heavily on my conscience, and I would feel responsible. I can't have that guilt when I face Raphael."

It had the effect he expected.

Jill released his hand and jumped up angrily. "That's bullshit!" she exclaimed furiously. "And you know it! You care about me, Castiel! Admit it!"

Castiel slowly got to his feet. "I… I have to go," he said uncomfortably. He didn't want to witness her pain any longer.

"Of course you do!" Jill fumed. "You're too big of a coward to admit you have feelings, so you gotta fly off!"

He tried desperately to keep the devastation he was feeling off his face. If she only knew… He was doing this to protect her. If Raphael found out that he was becoming attached, Jill would never be safe again, and it would be his fault.

He turned away from her without a word, preparing to leave, but she grabbed his arm. He spun back around to face her and was shocked to see that the fury on her face had been replaced with something like desperation. "Cas, wait!" she pleaded. "I'm sorry! Please don't go!" He just stared at her, not trusting himself to speak. "Will I… will I ever see you again?" Her eyes became misty, and he began to panic. If she started to cry, he would lose his uncaring act in a heartbeat.

So he did the only thing he could think of.

Before she had time to react, he touched two fingers to her forehead, and she collapsed in his arms. He carefully laid her down on the park bench, hoping that the children hadn't seen anything.

There. It was done. Now he could leave.

But something stopped him.

On a sudden whim, Castiel reached into his pocket and pulled out the penny that Jill had given him that night. He placed it in her hand and curled her fingers around it tightly so she wouldn't drop it. Maybe one day, when the war was over and everything was back to normal, he could come back and beg for forgiveness.

"Goodbye, Jillian," the angel whispered, his voice getting caught by the wind and carried away as he left Chicago.

~Supernatural~Supernatural~Supernatural~

Castiel flashed up to Ken Lay's Heaven, the place where he'd been summoned by Raphael the time before. He could feel the 50,000 souls that Crowley had given him moving around in his vessel and filling him up with power. Souls truly were the eighth wonder of the world.

Sure enough, Raphael was there. Castiel barely registered the shock on the archangel's face before he swept his hand through the air, banishing Raphael from the room. If 50,000 souls could give him this much power, he could only imagine what all of the souls of Purgatory could do.

"There will be no Apocalypse," Castiel announced to the empty room, but he knew that every other angel in Heaven would hear the words he was speaking. "And let it be known: you're either with Raphael… or you're with me."

Now Castiel had a chance. If he and Crowley could find Purgatory, he would be unbeatable. The war would be won, and the Apocalypse would be halted once again. And if all went as planned, Dean would be able to stay normal and happy with Lisa and Ben. If anyone deserved an easy life, it was Dean. He just hoped that Sam being back wouldn't ruin it…

And then there was Jill. She would forgive him—she had to. He would do everything he could and more to earn it. Nothing would stop him from making it up to her. That look of desperation and dismay on her face when he was leaving would haunt him until he made her smile again. And he would make her smile again.

He was an angel of the Lord—how hard could it be?