Six months later

Dean hit the ground with a hard smack. He gasped for breath and groaned. He was sure he had broken a rib in his fall but still managed to scramble up. His eyes searched wildly for the angel of the Lord.

"Cas!"

But the only answer he got was the soft rustling of the tree leaves above him as the wind blew through them.

"Goddammit, Cas... I'm sorry."

They'd been so close. So close to finding a way out of Purgatory together. But Cas hadn't made it to the portal in time. That son of a bitch...
After killing Dick Roman, that Leviathan bastard exploded in black ooze and dragged them to Purgatory. Dean got separated from Castiel (who was suddenly completely sane again) a couple of times and spent so many days and nights running and fighting all kinds of monsters. Only three things had made Dean hold on; his Hunter skills, an unexpected alliance, and the will to get back to the woman he loved.

"Allegra? Allegra, can you hear me?"

Dean held his breath, waiting for some sort of sign. But just like with Castiel, nothing came.

"Dammit! I'll find you, Alley. I just need to know where I am first."

He looked about him again, anxiety creeping up as he took in his surroundings - dark, scary forest, middle of the night, nothing or no one in sight. This was the exact same setting he found himself in months ago upon arriving in Purgatory. Wait, was it even months?
Time passed differently in Hell and Heaven; it was only fair to assume it was the same in Purgatory. It could be days, weeks, months, or even years later! Worse, the portal could have been a hoax or trap, and this could still be Purgatory!
He had to move. He just had to start moving and keep an eye out for anything that might...

"You're back!"

Dean jumped and turned around, ready to defend himself.

"Wow, wow, Dean, easy! You're safe! You're back in the real world!"

A beautiful young woman stood before him. She had long black hair down to her waist, a honeyed complexion, Mediterranean, maybe, and light brown almond-shaped eyes. She was dressed in a lavender-colored sleeveless dress with tiny hearts stitched on the skirt.
The woman held her hands to calm him down. But after God knows how much time in Purgatory, Dean wasn't just about to trust the first person that popped up in front of him.

"Who are you?" he demanded.

"My name is Amore. I'm a Cupid."

Dean groaned silently. Meeting the last Cupid had been one time too many. Little butterball had been stark-naked and way too emotional. This chick was definitely an improvement, but why would a Cupid be here for him?

"Dean, I promise you I am only here to help you."

She took a step closer and touched his chest with the tip of her fingers. Dean immediately felt stronger and healthier than he'd been in a long time. The constant pain his body had gone through since falling into Purgatory was just erased.

"You'll probably be hungry," continued Amore. "I'll take you somewhere you can rest and eat and fill you in on everything that's happened here."

"No offense, sister, but I'm not just gonna go off with the first person I encounter after spending way too much time in the freakin' Twilight Zone," said Dean. "I appreciate you healing me, but I can make my own way from here."

"So you don't wanna get back to Allegra then?"

Dean stared at the female Cupid.

"You know Allegra?"

"Not personally in the sense that I met her and spoke to her, but yes. She's kinda our leader now."

"I'm sorry, did you just say Allegra is your leader? Allegra? The hybrid Archangel who killed an angel last time you messed with us? Allegra?"

"This isn't really the best place to talk about things, Dean. Will you please let me take you somewhere safe first? I'll tell you everything, I promise."

Dean looked Amore up and down with narrowed eyes. She seemed sincere enough. A demon wouldn't pose as an angel, much less a Cupid, to get close to him. They would just attack him head-on.

"Fine, I'll take a leap of faith here. But you make one wrong move, and your Cupid days are done, got it?"

"Yes, I understand."

"We have to make a stop, though," added Dean as Amore stepped up to him. "I need to keep my end of a bargain."

She tilted her head quizzically but didn't ask any questions. Dean took her hand and told her to go to Louisiana. Time to get the soul of the hitch-hiking vampire out of him.

***

After Dean dug up Benny's grave and resurrected him, the pair said their goodbyes, wishing each other well. Dean hoped he would see Benny again someday 'cause he was a pretty stand-up guy for a vampire. If it hadn't been for Benny, he wouldn't have survived Purgatory. That was a fact. He felt good that he was able to bring the vamp back as a thank you.

At least someone I was able to save...

Amore had watched silently, not making a single comment as Dean brought back the vampire. He was a bit surprised at that, having figured she would have put up a fight or something. But Cupids were lovers, not fighters. Whether or not a vampire was alive wasn't Amore's concern; bringing him back to Allegra was, which she made clear as they sat down together in a small little hunting lodge not too far from Benny's gravesite.
Amore conjured an entire table full of food, making Dean realize how hungry he was. He grabbed a beer and a couple of burgers and sat across from her. Now that he was somewhere seemingly safe and warm and with a hot meal, Dean jumped right into it.

"Where's Allegra?" he asked. "Is she okay?"

"Physically, yes. Emotionally is another matter entirely."

"What happened to her?" Dean felt his heart clench in fear. "Is Sam still with her? Oh God, don't tell me he's..."

"Dean, calm down." Amora held up her hand to silence him. "Sam is doing fine. He's not possessed by Lucifer, nor is he with Allegra. They haven't seen each other in months."

"They haven't?" The reply came out a little more joyful than Dean meant.

"I don't know the details, but from what I understand... Sam gave up on you. Allegra wouldn't, and they fought. She left him and went to Kansas. I don't have an exact location - none of the angels do. But I can take you as close as I can when we're done here."

Sam gave up... Allegra didn't... And she's in Kansas? Could she be at the house? She hates it there. Why would she...

Dean suddenly realized there would only be one real reason for Allegra to return to her childhood home - for him. He had asked her to meet him there when all that crap with the Leviathans was done. 

She's been waiting... this whole time? Alley...

"He was right."

Dean was pulled out of his thoughts by Amore's voice. He looked up at her and caught her smiling.

"What?" he asked, confused. 

"Your heart rate just changed drastically in the last minutes. You got agitated when you believed something had happened to Allegra. Then your heart skipped a beat when I told you Allegra and your brother weren't together. And now, it's slowing down as you realize that Allegra left Sam because she wouldn't give up the search for you. You're realizing that she's waiting for you to return. In these past minutes, your love for Allegra has multiplied tenfold. I was initially skeptical considering your... romantic history, but I must admit, Gabriel was right about you."

"I'm sorry, Gabriel?" Dean's eyes widened in surprise. "What does he have to do with any of this?"

"I had a brief dalliance with him a couple of decades ago." Amore blushed a little. "He wasn't one for actual relationships, but it was fun while it lasted. Really, really, fun... Ahem, anyway, Gabriel reached out to me a few days before his death since he knew I was Allegra's Cupid. He wanted me to keep an eye out since he had asked Balthazar to make sure Allegra learned about the prophecy and told me he was certain you were the right guy for her. I have to say I was leaning more toward Sam at the time, but I can see now why Gabriel thought you were the one."

Dean was left stunned at that. Gabriel, that lame excuse for an Archangel, the guy who walked out on Allegra - on her birthday no less - thought he was the right guy for her?! He recalled the somewhat disturbing message Gabriel had left for him on the Casa Erotica DVD a couple of years ago. He'd asked Dean to take care of Allegra. He could've also asked his brother, but no, the request had been made to Dean and Dean alone.
But that wasn't the most shocking piece of information Dean had just heard.

"What do you mean when you say you're Allegra's Cupid? I thought she couldn't be with anyone?"

"Well, no one except the person she is destined to be with, being either Lucifer or Michael's vessel. Meaning you or Sam."

Dean's mouth dropped, and Amore tilted her head to him.

"You do know about that part of the prophecy, don't you?"

"Does it look like I do?!"

"Oh wow, okay, I hadn't expected I needed to explain this to you. In short, Lucifer and Michael can't do anything with Allegra unless they are in the right vessel. That's the real kicker. The power lies in the vessel. Only you and Sam can be with Allegra."

"That I know. But I ain't ever saying yes to Michael, and neither is Allegra, so it's not happening for us."

"Dean, you're not hearing me. It's not about the Archangels; it's about the vessels. You don't need to be possessed by Michael. He is dependent on you, but you aren't on him."

Dean stared at Amore. Was she seriously saying what he thought she was saying? Could they... actually...?

"How do I know you're not lying?" he questioned.

"Oh, sure, because killing the other only guy Allegra ever wanted to have sex with wasn't enough. I wanna see you burn from the inside out as well just 'cause I feel like it."

"Wow, wow, rewind a second! Did... Were you behind Eric's death?!"

Amore sighed and ran a hand through her hair.

"Look, I can't do what I normally do with Allegra, okay?" she said. "'Normal' doesn't apply to her. I can tweak the game a little and give a nudge in the right direction, but that's it. My main task with Allegra is ensuring she doesn't end up with anyone else besides the chosen vessels. I amplify her... passion, for lack of a better term, so that it comes out and takes effect if she's not with the right person. For the greater good."

"The greater... Well, you did a hell of a job on that one, lady! You got any idea how much that night messed with Allegra?! She blames herself for his death and is convinced she's cursed or something!"

"I know, Dean. Believe me, I do. It pained me to do that, especially since I saw they really cared for each other and could have had something truly beautiful. But he wasn't you or Sam. And Allegra's isn't just anyone. With the right person at her side, she can do amazing things. Which brings me to this."

Amore placed a little box on the table in front of Dean. His breath caught when he recognized the jewelry box he had kept hidden in the glove compartment of the Impala.

Give heart...

"You need to tell Allegra that you love her. You need to give her your heart. Both literally and figuratively."

"I... I can't." Dean's anger ebbed, and he cast his eyes down. "She hates me for... the Amazon. And things I said to her."

"If she hated you, she wouldn't have kissed you that last time," pointed Amore out. "If she hated you, she wouldn't have spent the last 6 months trying to get you back. If she hated you, she would've stayed with Sam. I can go on, but I think I've made my point."

But Dean still felt uncertain. He had wanted to talk to Allegra after defeating the Leviathans about what he had found in those boxes Gabriel had stored and see if there was still a part of her that might be willing to give him another chance but now that he knew she had been waiting for him this entire time, it terrified him to go. His eyes fell back on the jewelry box. He reached for it and opened it, revealing the necklace he bought Allegra after that first amazing afternoon in bed together. If what Amore said was true... they could do that again. That and so much more. They could maybe even...

Our son...

"Answer me one more thing. Everything I feel for Allegra, and everything she feels for me; is that your doing as well?"

Amore hesitated a moment before answering.

"I enhanced your feelings in that parc in Oregon. You both needed a little push to finally say yes to each other. And I may or may not have tampered a bit with the radio in your car to give you a much-needed hint at certain points. But I didn't create your love as I do with others. I didn't ignite the spark nor create the 'happy accident' that brought you together. Your love was already there. It just needed to be let out."

Dean believed her. He didn't know how or why; he just did. Deep down, he had known all along. Not being with Allegra was like not being whole. He missed the most important piece of himself. It was time to get it back.

"Take me to her."

***

Nothing again. Allegra was getting used to her meetings with Naomi ending the same way over and over again. Staying nice to the angel for the sake of the other angels was starting to get really hard, but she refused to give in to Naomi's attitude. She hated to admit it, but she needed the angels. And they weren't all bad. Those few who had dared to speak to her (killing Hester had left a bit of an impression) did so kindly and with some reverence. They had definitely accepted her as the boss. For now, anyway.
So Allegra did her best not to get too angry with Naomi for being an incredible bitch most of the time and muddled through. And even if it took another 6 months, a year, a lifetime even, she wouldn't stop. Stopping wasn't an option. She would get Dean back... somehow.

In the meantime, though, Allegra decided to work a case in McLouth. Things were going from mildly weird to downright freaky, which wasn't good for a town with only about 1000 inhabitants. Everyone knew everyone, and when something happened, the entire town got affected by it. First, reports had been laughed away by police and the press. Cute pranks by teenage hooligans, they called it. But then the pranks got scarier. Wilder. Bloodier.

All right, what do we know? Hmm, someone broke into a toy store and burned all the feet away from the dolls. Birds attacked a pair of twins in the park and pecked their eyes out. Guy fell into a thornbush and got thorns stuck into... his eyes, too? A college student home for the weekend got attacked by a... wolf, seriously? What the hell is going on out there?

Allegra looked from the newspaper back to her laptop and then retook her notes. There was something familiar about all this. Like she had read about these occurrences before. But what could possibly cause a little mischief like smashing pumpkins in the middle of the road and putting frogs in people's pools to turn into... this?

She jumped when Trixie suddenly started barking loudly. The Australian Shepherd had been lying peacefully on the rug in the living room while Allegra sat in the dining room surrounded by whiteboards with newspaper clippings, photographs, and post-its with notes on them (her research on finding Dean and her Hunter cases had just managed to remain contained in that one room), but now darted to the kitchen. She barked and scratched at the door until Allegra finally came to see what all the fuss was about.

"Trix, what's the matter, girl?"

Trixie whimpered, turning in circles on the spot and jumping up to the door. Allegra was immediately on high alert. The dog wouldn't react like that unless something were up. The angels couldn't get here, nor could demons, but maybe some other monster could. She reached for the doorknob... and froze.

This feeling... That's...

Allegra pulled open the door. She stepped outside on the porch and looked around frantically. Her eyes finally found a figure approaching the fence on the other side of the yard. Her heart stopped, and her breath caught. She expanded her shield, allowing it to touch the man's soul. He stopped dead in his tracks, one hand on the gate, and looked up. Even from this distance, Allegra would recognize those green eyes everywhere.

***

They ran to each other, faster and faster. Their spirits soared. Their hearts raced. Their bodies yearned to feel each other's touch. This was a dream. It had to be a dream like so many Allegra had before. She had fallen asleep over her research, and the moment she would get to him, she would wake up and find herself alone in the dining room, and the dream would become the harsh and all too real nightmare she had been living for these past months.
But Dean didn't disappear. He only got clearer with every step. And when she finally fell into his arms, Allegra wrapped her own around his neck, allowing their lips to crash together in the most stereotypical epic Hollywood reunion kiss ever. It wasn't until she felt his body pressing against her own, when she tasted his sweet lips and got that warm fuzzy feeling in her stomach, that she truly realized he was real. He was here. Dean was here!

"You came back to me." Allegra's eyes glistened with tears as she smiled in their kiss.

"Of course, I came back." Dean cupped her face. "I'll always come back to you."

Their lips met again.

"I never stopped looking for you."

"I know."

And again.

"Dean, I love you."

"I know."

And again.

And from the grove in the distance, the Cupid who brought Dean Winchester back to his destiny grinned at the angel beside her, sensing Allegra and Dean's love grow more powerful than ever.

"Match made in Heaven. Don't you agree?"