Disclaimer: I don't own either Good Omens or Supernatural but I do own my OC.

Author Note: I have no clue how Cupids work in the Supernatural world, so I've created my own system that I think would fit in the Good Omens world.


Chapter 1- The Genius Plan

Monday

Emmy was feeling seriously annoyed. This was a very rare occurrence, as she was likely one of the calmest and happiest cupids you would ever meet. In fact, a friend[1] had once said, "If Emmy was any more laidback she'd be horizontal."

Oddly enough, her bad mood had nothing to do with the fact that she was sat in a tree in the middle of night [2] when she would much prefer to be in a nice warm bed or at least a house. It also, strangely, had nothing to do with the fact that it was raining, or the fact that when the rain and the night were added together it made the visibility of the evening comparable to that of the bottom of the Mariana Trench.

Her mood was acerbated slightly by a branch above her head that had been placed at exactly the right angle for a continuous drip of water to run under her already soaked coat to have a go at soaking the shirt underneath. But really that was just a momentary annoyance.

No, the real source of her bad mood were the two humans she was peering at through the slanting rain.

Sam and Dean Winchester, the humans in question, were currently digging up the grave of a vindictive bitch of a ghost that was killing everything that took one step into her old house. It had, thankfully, been a pretty simple 'salt and burn' kind of hunt and the boys had managed not to need supernatural assistance for once. She had saved both their arses on multiple occasions before this hunt, never appearing directly of course. They wouldn't take kindly to being followed by anything, let alone something supernatural.

They'd finally reached the coffin after a good few hours of labour and soon the body was aflame and they could all go back to the motel before moving on to the next hunt, be it demon, ghostly or just some weird thing nature cooked up. That was the hunter life.

Following the hunter's around and joining in on the hunter lifestyle the two men lead, was also not what was annoying her, even though Emmy didn't particularly enjoy the scratchy motel sheets or the leaky faucets of the crumbly places they were forced to stay in. She kind of enjoyed it actually, spectating the actual hunting was quite fun and much more interesting than what she was used too [3].

Emmy hopped down from the tree, making no moves to be quite, knowing that the boys could neither see nor hear her if she didn't want them too and followed them back to Baby and settled cross-legged in the back seat.

"Watch it, Sam! You're freaking girl-hair is dripping all over the leather!" Dean complained as he settled behind the wheel.

"It's hardly my fault it started raining!" Sam, returned glaring at his much shorter older brother.

"Whatever, Bitch."

"Jerk."

Emmy grinned at the back of their heads, listening to the brotherly insults as the banter continued. She honestly liked the two brothers which made her job much more fun and usually easier.

And that was the problem, they weren't making her job easier. After all, it's pretty hard to set two people up if their living in different countries and no matter how many interesting demonic omens and potential cases she made sure they noticed in London, England they never showed a single interest in hopping aboard a plane. It had been aggravating her for weeks and this morning she had found out why they never left the USA.

Dean Winchester, the second most badass person she'd ever met [4], was afraid of aeroplanes. Dean Winchester, the man who bitch slaps demons and shanks ghosts, afraid of a little man-made flight. She was pretty sure the statistics for death by ghost was higher than plane crashes. Aziraphale would probably have a statistic for that.

Thinking of Aziraphale made her scowl as a vaguely guilty feeling settled in her gut. Aziraphale and Crowley despite his demonic status, had been her best-friends since the dawn of time and she didn't enjoy manipulating them, even if it was for their own good. And gaining their soulmates was undoubtedly good for them both. It was a very annoying part of her job that it was frowned upon to just appear to a guy, point out his soulmate and to leave again. No, some finesse was expected, some kind of interesting plan carefully sculpted to yield maximum results.

Meaning she couldn't just turn up in Crowley's Bentley and point him towards Dean Winchester and likewise with Sam and Aziraphale. She had to produce a plan, a genius plan that guaranteed results. Most importantly she needed to get them both to Heathrow Airport.

The banter had dribbled to a stop and the soft sound of Sam's snores could barely be heard over the melodies of Led Zeppelin that slid out of the car CD player. Dean hummed along, tapping his fingers in time to the beat and throwing glances Sam's way every few minutes. That was one of the reasons she liked Dean Winchester, she thought as she turned to lie on her back and crossed her right leg over her left, his intense loyalty to those he loved.

And that was the key, that family loyalty. Emmy knew that Dean would only get on an aeroplane if he needed to and she could only think of one thing that would get him on a flight to England. [5]

Sam. Dean took the title of 'protective older brother' seriously, the guy would literally sell his soul for him. If she took Sam, held him in London, Dean would get right on that plane.

No, she couldn't look after Sam herself, he'd easily escape or just overpower her. The guy was a freaking mountain, he could probably bench-press her. And she couldn't watch both Sam and Dean at the same time. And what would happened after, how did Crowley and Aziraphale fit?

She was on to a winner with this idea, she knew it. It had been circling her thoughts all day.

She could leave Sam with Aziraphale, he was an Angel of the Lord after all, and he wouldn't be overpowered. No, Aziraphale was too kind-hearted to keep somebody prisoner, Sam could easily manipulate the Angel with his puppy dog eyes and persuade him to loosen the restraints enough that he could get out. And Aziraphale would never get with someone left under his care like that. His morals were too strong.

Crowley, however, would be quite a good prison guard. He was almost impossible to manipulate unless you'd known him long enough to earn his trust [6]. Plus he had just fluid enough morals that he wouldn't be above getting with a prisoner.

Shame he was Dean's soulmate and not Sam's.

When she realised how stupid she was being, a few minutes later, she face palmed and muttered, "Bloody Hell, Emmy, you are off you're game. This is what four years of time off does to you."[7] She had been fixating too much on overcoming Dean's fear of flight when she had a perfectly non-scared client to fix up too. "Idiot." She admonished herself again as she formulated a quick plan in her head.

She grinned, it's a genius plan, she thought before disappearing to England.


Crowley was asleep. As a demon he didn't really need to rest, but after spending 6000 years on earth, he'd grown accustomed. He enjoyed being able to slip into unconsciousness every now and then and not have to deal with keeping out of the way of the powers that be.

So you can imagine why he felt rather disgruntled when he was roughly shaken by the shoulder and awoken by a familiar voice saying "Wake up, Snakeface."

He growled out a sleepy "Piss off." and curled into a tight ball around his pillow. He heard an exasperated sigh, slight movement and then a pillow was forcibly smacked into his face. He let out a sound that he would later protest was most certainly not a squawk and bolted up right, glaring at Emmy's smirking face.

"Emmy!" He growled out, in a tone which suggested imminent death, "What are you doing?"

"Waking you, moron." She said, her voice affectionate. "Get up."

"What time is it?"

"About 6:30am. Now get up, you stubborn demon. I want to meet you and Aziraphale in St James at about," she paused looking at her watch, "ten o'clock."

"Why'd you wake me so early then?" he muttered peevishly still angry about the impromptu pillow fight.

"Oh, shut up, it's not as if you need sleep. Just be there, I'll buy you both coffee from that café you both love."

"Fine." He grumbled, "But this better be important. And I want a bagel too. "

Emmy rolled her eyes and left before the angry demon came up with more demands.


On the other side of London, Aziraphale was awake. As an angel, he didn't need to sleep either, but unlike Crowley he had never quite seen the appeal of lying comatose on a bed thus he'd never bothered.

The back room of his bookshop in Soho was quiet apart from the turning of pages and the slight murmurs of "Fascinating." When he came across a surprisingly accurate prophesy. The cup of cocoa at his side had mould so advanced it was beginning to develop rudimentary speech and had been completely ignored for about a week.

Aziraphale was so involved in his book in fact, it took him a good few minutes to realise that Emmy had appeared at his table and was sat watching him with her head resting on her hands.

She smiled fondly at him when he finally looked up and said, "Heya, Angel Cakes."

"Emmy, My Dear, what are you doing back here so soon? I thought your latest job was in America?"

"I am, that's why I'm here actually. I need your help, Angel Cakes."

"Oh, well, of course, I'll do anything, Emmy Dear." He placed the book gently to the side, noticed the mouldy cup for the first time and banished it to the sink before looking back at his friend. "What can I help you with?"

"Can't tell you yet, Angel Cakes. I need Crowley too. You free at ten to meet us at St James?"

"For you, Dear, anything."


Footnotes:

1. One A.J Crowley

2. It was actually about 12:40 which is close to the middle of the night

3. What she was used to was usually boring, old office romances where both parties were too scared to ask the other out for fear of rejection. Too boring for words.

4. The top spot being held by both Crowley and Aziraphale. After all anyone who would willingly go to fight Satan armed only with one solitary flaming sword and a tyre iron is very deserving of joint top spot.

5. Aside from demons.

6. Long enough in this case was 6000 years give or take a few.

7. She had gained the time off, because four years ago when the-apocalypse-that-wasn't occurred many people in Emmy's area at the time, including her clients, got over themselves and went after those people they'd been too scared to do so previously. The day after when the memories were wiped from everyone's minds, her bosses, believing that Emmy had somehow made about fifty couples get together on the same night, gave her a commendation and time off. She spent that time off getting drunk in the backroom of a bookshop in Soho.