A/N: I'm really enjoying writing this story, and I dearly hope you come to love it as well. I'm motivated by response, so the more I get, the more likely I will continue this in a timely manner. :) So please, let me know what you think!

Disclaimer: I do not own Supernatural, or any of its characters.

~For the Gabriel in my dream~

Thank you for making sure I wasn't left behind.

It's because of you I was able to save my family from the Weeping Angel apocalypse.

Chapter One

"Fold." Cupid slapped down his cards in annoyance and picked up his glass of wine, swirling it gently before taking a swig.

Gabriel smiled—although he was well aware that his smiles often came off more as smirks. And he would have it no other way. He set his cards face up on the table. "Full house," he said, and took a sip of his own wine before collecting. "Shall we go for another round?"

"Why not?" Cupid reorganized his already organized chips, then leaned back as he watched Gabriel shuffle. "What you think of the Winchester situation?"

"What?" Gabriel dealt the cards. He glanced up at Cupid's raised eyebrows. "Oh, you mean with dear old Dean and that mark? The Mark. Of. Cain." He shot each word of the phrase out, finishing his deal and settling back in his chair, fingering his chips. "Five in."

"I raise." Cupid put in fifteen.

Gabriel smirked again, and glanced down at his cards, even though he knew he would have a favorable hand. And if not, he would give himself one. One of the perks of being the Trickster. As long as Cupid didn't catch on…

"So… what do you think?" Cupid prodded again. "Do you think the rumors are true? That Dean was killed and came back as a demon? A powerful one at that. And is now working for Crowley, of all people…"

Gabriel traded out his cards. He was going to have a straight flush, if he was lucky. "I've learned to stay out of Winchester business," he said absently, chucking a few more chips into the pot. Cupid followed suit, but frowned at his cards.

"Ah, yes. You still haven't told them?"

Gabriel huffed out a laugh. "As if. Why would I do a silly thing like that?"

Cupid shrugged. They were silent for a moment as they continued their game. Cupid spoke up again. "You know… If Dean's a powerful demon now, there's nothing we can do to change that."

"Nnnnnope." Gabriel took another gulp of his wine.

"But." Cupid leaned forward, as if about to share in some conspiracy theory. "We angels in Heaven arranged a little plan to deter Cain from his… violence."

Gabriel silently snickered at Cupid calling himself an angel. Cherubs were barely heavenly beings. He pulled a tootsie pop out of thin air and ripped off the wrapper. "Lemme guess. You hooked him up?"

"Well… yes. I mean, Cain and Colette were destined for each other. We got the orders, we shot, and presto! Cain was suddenly a loyal dog to that human. Very sweet."

Gabriel stuck the tootsie pop in his mouth and smirked around it. "If you say so."

"I'm done playing," Cupid said, setting his cards down. "This angel knows when he's been toyed with the Trickster." He gave Gabriel a meaningful look, to which Gabriel tried to look innocent. And failed. But hey, Cupid had it coming.

"You know," Cupid said, making himself even more comfortable in his chair, "I could look into Dean Winchester's destiny. See if he has any future love interests that could become his… salvation, you could say."

"And why would you do that?" Gabriel said, standing. They were in one of Gabriel's hidden get-a-ways. This one was a nice celebrity mansion in New Jersey that was perfectly immaculate and very modern. He made his way into the grand living room, where a giant flat screen waited for him. Cupid followed him in, forcing a disbelieving laugh.

"Dean Winchester is terrifying as a human alone. Can you imagine what he can do as a demon? The way he is now, he is Crowley's biggest weapon."

"Against what?" Gabriel asked, plopping down on the leather couch. "Heaven? I think Crowley's tied up in trying to fix up Hell currently."

"Yes, but then what?" Cupid sat in a large over-stuffed chair, leaning forward. He reached for one of the many cupcakes sitting on a stand on the table in front of him, peeling off the paper lining and popping the whole thing in his mouth. He spoke around the cupcake. "He'll cause a lot of destruction here on Earth. Don't you think he'll make his way up eventually?"

Gabriel shrugged. "Crowley is relatively harmless. He goes by a code. Dean, however…" he popped his tootsie pop back in his mouth, sucked on it, and drew it out, pointing the shrinking orb at Cupid, "Dean could definitely be a hazard when he's let off the leash."

Cupid grabbed another cupcake. "Say we attempt to avoid that. Don't you remember how it used to be, Gabriel? We used to help people."

Gabriel shifted so he was leaning against the arm of the couch, feet stretched out in front of him. "Yeah, well. That was then. This is now. I'm not coming out of hiding because the Winchester boy was stupid enough to take on the Mark. Let Sam and dear Castiel figure it out. They usually think of something."

Cupid was silent for a moment. He had eaten four cupcakes, but now he stared at his meaty hands in silence. "What if… What if we make a deal with Sam? I'm sure he'll do anything right now to get his brother back."

Gabriel raised his eyebrows. "A deal? Since when do you make deals?"

"I don't normally. But you do."

Gabriel rolled his eyes. "Winchester's can't know I'm still alive. I want to pop up at the opportune moment, if that moment ever comes. And currently, this isn't it."

Cupid frowned. "Well then… I can just go offer my services for free." He stood. "Like a good angel should."

Gabriel sat up. "Leaving?"

"I've worn out my stay, I believe." He opened his arms wide.

Gabriel sighed, and stood. "Just… don't…"

Cupid wrapped his large arms tightly around Gabriel and squeezed, making Gabriel choke. He patted him awkwardly on the back. "Okay, Cupid. Enough's enough."

Cupid stepped back with a grin, lightly punching Gabriel in the shoulder. "Sure you won't join me?"

Gabriel ran a hand through his hair. "Well. Now that I think about it…. I'd like to be kept up-to-date on this. So… you go offer your, uh, services to Sam Winchester, and, well… let me know how it goes." He pointed his tootsie pop at Cupid again. "I'm interested to see if Dean is… destined for someone, as you say."

Cupid's grin grew wider, and he slapped Gabriel on the back again. "Will do, brother. Until then…"

He was gone.

Gabriel stood in silence a moment. It was nice having Cupid over once in a while. He was one of the very few who knew he was still alive. And Gabriel intended to keep it that way for a long time.

But, as he settled down to do as he pleased, he was struck by a loneliness that wasn't altogether new. It got lonely when he couldn't trust—or be trusted.

Maybe… maybe he was interested in messing with the Winchesters again. But the Trickster didn't trick just because. There had to be a purpose behind it.

So he'd keep tabs on them through Cupid. Maybe he would learn something worthwhile.

Sam took another swig of his beer, then set it down on the table with a clack before scooting closer to his open laptop and typing in another search term. He glanced up when Castiel walked in, and cleared his throat. "Find anything?"

Castiel shook his head, and took a seat across from Sam. "It's like he vanished into thin air."

Sam sighed, leaning back in his chair and swiping a hand down his face, then shaking his head to try and clear it. He'd never gotten much sleep most his life, but this hunt for Dean was really draining him. "We'll find him," he finally said. It had only been two weeks since Dean's disappearance. They would find something eventually.

Castiel answered with silence before getting up from his chair and pacing around the room.

Sam suddenly couldn't take the silence any longer, and stood from the chair in frustration. He swiped a hand through his hair. "I just don't get it," he said, "Dean died in my arms. I'm sure of it. I dragged him all the way back here."

"Sam, there's no need to—"

"No," Sam interrupted. "No, I need to go over this again with you. So our theory right now is that Crowley brought him back. But why?"

Castiel sighed, and took a seat at the table. "Maybe… maybe he wants Dean's help with something."

"Yeah, maybe." Sam paused, thinking. When he had summoned Crowley the night Dean died, he never showed. And then when he went to visit Dean in his room, he was gone, along with the first blade. That was all Sam knew. He'd tried summoning Crowley several times since, to no avail. He and Cas had trapped several demons to get more information, but they didn't know where Crowley or Dean was.

They had caught onto a rumor, however. But it was so disturbing that Sam dismissed it from his mind, even though it plagued him day and night. But it was just a rumor. Not even the demons could prove or guarantee the validity of it. Wherever Crowley and Dean were, they were keeping it very hush-hush.

Sam and Cas had also entertained the possibility that Crowley had nothing to do with it. Something else could have happened to Dean. His body could have been taken for unknown reasons.

The angels had no idea what had happened either. Castiel was suddenly on good terms with most of them again, so it didn't seem like they would lie. However, they were the ones who told them about the rumors.

No, the best theory they had was that Crowley had brought Dean back to life and was holding him hostage somewhere. Or Dean had gone with him willingly. They had been a little friendlier with each other the last few weeks of Dean's life…

…But why wouldn't he tell Sam where he was?

"Helllllllooooo dear boys!" Sam nearly fell out of his chair at the sudden noise, and Castiel shot up from his seat.

"…Cupid?"

Now Sam recognized the pudgy cherub who was (thankfully) wearing clothes this time. A nice suit and a bow tie. The lower class angel grinned from ear to ear as he spread his arms wide. "Miss me, Castiel?"

Castiel groaned, but Cupid popped up behind him and wrapped his meaty arms around Castiel's stiff frame and lifted him from the ground. "It's good to see you, brother!" He suddenly froze, and put Castiel down slowly. "Castiel," he said simply.

Castiel ducked his head down, then looked up at Cupid. "Yes, my, um… my grace…"

"I can feel that stolen grace burning up inside you, brother. You can't hold out forever."

Castiel nodded. Cupid clasped him on the shoulder, then turned to Sam, his grin returning to full strength. He stretched his arms out.

Sam forced an awkward smile. "Uh, hi." He knew there was nothing he could do to stop the crushing hug, so he stood there and allowed it to happen. He was sure Cupid cracked some of his ribs.

When the angel finally stepped back, his face suddenly turned sober. "Now. I'm here on some serious business. I have a solution for Dean."

Sam and Castiel exchanged glances. "You know where he is?" Sam asked.

"Well… no. But when you do find him, I have a way to cure him! Well, not cure him exactly, I can't do that. But see, with Cain…"

"Woah, woah, woah hold up." Sam took a step closer to Cupid. "What do you mean, cure him?"

"Well, as I just said, I can't exactly cure him, but Cain—"

"Cupid, just shut up for a second, okay? Cas and I aren't following you."

Cupid froze, and looked from Sam to Castiel and back again. "Wait… so you don't know?"

"Don't know what?" Sam pressed.

Cupid's face fell. "Oh, boys. You'd better sit back down for this. I never dreamed I'd have to be the one to tell you."

A sickening, sinking feeling writhed in Sam's stomach. He took Cupid's advice and sat down. Castiel stood standing.

Cupid took a deep breath. "Well, there's something about Cain that not many people know. When he learned what he'd become, he killed himself with the blade. But… the mark wouldn't let him go that easily. It brought him back. But not in a good way…"

Sam already knew what Cupid was going to say. Castiel said it for him. "He came back as a demon."

Cupid nodded.

Sam filled in the blanks out loud. "So you're saying… that when Dean died… the mark brought him back as a…." He couldn't even say it. He sat back in his chair, exhaling slowly. "So then the rumors are true."

"I'm sorry to have been the bringer of bad news. But I have something of a solution."

Sam was too stunned to speak. Castiel spoke for him. "Let's hear it."

Cupid pulled up a chair and sat, leaning forward. "Okay. So. When Cain brought about his reign of terror, it was ugly. Heaven had to step in. But we didn't want to smite Cain down… and anyways, that would have been nearly impossible. Maybe Michael would have been up to the task, but…" He shrugged. "There's not much that can kill a demon as powerful as Cain was. But we also knew that he didn't want that life. We knew it was the mark, and the blade, that was doing this to him. So. We decided to clear up some of the dark fog." Cupid grinned, looking pleased with himself.

"It was one of the most important missions in Heaven. We had to find Cain's soul mate. His… salvation, if you will."

"Colette." Sam remembered Dean telling him that part.

Cupid nodded. "But you see… we love angels can't just shoot whoever we want and expect it to work out. They have to be destined for each other. Unfortunately, Colette wasn't even around until centuries later, but when we found her… we got them together." He grinned, then shrugged. "And sure, she didn't cure him. But she sure made him a lot nicer."

Castiel spoke. "So you're saying we should find Dean's soul mate to try and get him to come around…"

Cupid shrugged. "Like it or not, Dean is going to become a very nasty person, if he isn't already. He and Crowley, working together… You don't want that."

"No, we don't," Sam murmured.

"So you can find Dean's soul mate, then?" Castiel asked.

"Yes. Perhaps. If I had something of Dean's. I can see a… a vision, if you will, of who this person might be. Keep in mind, though," Cupid said, raising a finger, "She might not be around yet."

Sam nodded. "Understood."

"Sam." Castiel laid a hand on his shoulder. "We need to talk in private for a moment." He looked to Cupid. "Do you mind?"

Cupid leaned back in his chair, looking completely at home. "Take all the time you need."