• Published 5th Sep 2017
  • 1,380 Views, 21 Comments

Five First Dates - Sixcardroulette



So, Applejack is in a relationship now... with a human. Hilarity ensues. Sort of.

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Prologue: How You Gonna Keep 'Em Down On The Farm?

Matthew Williams was having a strange week. By his recent standards, that was really saying something.

A few months ago, he'd been stuck in a rut. A Californian, he'd pitched up in New York City, thinking himself lucky to find a decent job and a nice enough apartment, but his life had been going nowhere. Every day, he woke up, went to work, came home in the evening, played video games, went to bed, woke up the next day, went to work. Lather, rinse, repeat. Sometimes he'd change things up a bit by watching TV or going to the movies. He'd had big dreams once, but after a few years in New York, the only thing he'd really clung on to was a vaguely defined plan to one day quit the mall and travel the world.

Fast forward a few months, and instead of travelling the world, he was settling down in a brand new world, a world with new rules, where almost everything he'd ever learned was turned on its head. He would have called it impossible, except that the entire concepts of "possible" and "impossible" had changed forever. Questions - about how things worked here, or why certain things happened, or what was going to happen next - would only lead to more questions, and the nagging sense that he was either crazy, or at least headed that way. Instead, Matt was learning to just go with it.

There were worse places to settle down, all things considered.


Sweet Apple Acres. A hot, sunny Tuesday morning, the sun climbing higher in the sky, the air getting hotter, a welcome breeze filtering through the trees from time to time.

Down in the orchard, Matt wiped the sweat from his brow for the umpteenth time and cricked his neck, and looked around. Rolling hills covered with apple trees as far as the eye could see, in every direction, under a perfectly clear blue sky. He was pretty much used to the bright, colourful scenery, the way everything looked slightly unreal, but the view out here still inspired a bit of awe. The clean, fresh air carried the scent of leaves and apples. He felt lucky to be here; okay, so he hadn't exactly pictured himself working on a farm before, but it turned out he loved it.

"It's funny," Matt thought to himself, as he hoisted a barrel of apples onto a cart. "This was shaping up to be a pretty ordinary week. Or, it would have been, if -"

His train of thought was interrupted by a passing cow.

"Good morning, Matt," said the cow, with a friendly nod.

"Good morning, Patsie," replied Matt, without giving it a second thought.

He reached down to lift another barrel of apples onto the cart. He grimaced as his pant leg brushed against a scratch on his calf. Not Spike's fault exactly, he thought; he just needed to be more careful around the back-talking baby dragon and his sharp claws. After all, Spike was a decent guy, really. He was also effectively Matt's housemate: a live-in assistant to the magical unicorn librarian with whom Matt was currently crashing, by order of a sun-raising alicorn Princess who ruled this world of talking ponies.

Yep, quite a normal week in the new life of Matthew Williams, the first and only human in Equestria.


Even with the bar set pretty high, though, this had been a strange few days. "The good kind of strange, though", Matt reflected, as the main reason for all the recent weirdness trotted into view.

Applejack was glowing with perspiration as she took her hat off and shook out her mane. "Hooo-eee! Ah'm on a roll today," she grinned. "Ah musta cleared half o'the south-east orchard! An' it ain't even midday yet."

Matt looked over to her. She looked back at him. Their eyes met for a moment. They shared a smile. They heard a noise. They quickly looked away from each other as her brother came into the grove.

"How are you gettin' along there, Big Mac?" asked AJ, as breezily as she could muster. "Hittin' all yer targets?"

"Eeyup", replied the enormous red horse, with a proud swish of his mane.

"Well, keep it up!", beamed Applejack. "You too, Matt. There's a bunch o' bushels just waitin' to be loaded over behind them there trees, whenever ya find a minute."

Matt smiled. "Thanks AJ, I'll be over in a sec. Just need to finish up here."

They shared another look while Big Macintosh's attention was elsewhere. Wordlessly, Applejack and Matt let their gaze linger on each other, until the apple barrels on the cart gave a jerk as her brother heaved the yoke back onto his neck. Startled, they quickly looked away from each other once again. Big Mac looked back to make sure all the barrels were loaded; AJ fussed with her tail ribbon, and Matt pretended to be intensely interested in a piece of bark from the closest tree. It was too obvious, and things were too quiet; but luckily for them, Big Mac wasn't paying any kind of attention to anything but apples.

Still, Applejack jumped in to break the silence before things got weird. "Well, ah'd best be gettin' along. All them other trees ain't gonna buck themselves!" She gave another smile, and Matt's heart skipped a beat. "See ya both later," said AJ, as she trotted off into the distance. Matt stole a glance back towards her. She was looking back at him. Too far away to tell, but he thought she gave him another smile.

Matt was getting pretty good at reading AJ's face now. Smiles were pretty much all they could share in public; as far as anyone knew, he and Applejack were good friends, and they'd become closer friends after she found him a job on the family apple farm, where his hands came in handy lifting barrels for the ponies to speed up the never-ending harvest.

What everyone didn't know was that Matt and Applejack had fallen in love. Not only fallen in love, but slept together. And other than the Princess, nobody else knew just what was happening.

Keeping it that way was hard work, and both Applejack and Matt were getting tired of the charade.


Having arrived in Equestria by accident, with nowhere to live, Matt was currently billeted way across town with Twilight Sparkle in the library. He got to see Applejack at work every day, but with her brother and little sister tending to the farm too, and her grandmother supervising and keeping a watchful eye over the family, Matt's real time together with the pony he loved was limited to whatever precious moments they could steal when no other ponies were around.

'The pony he loved'. Now, that was a sentence he'd never expected to have in his head, for sure. Even without the whole "pony" thing, the idea of falling in love was strange enough in itself. But, despite never having felt it before, he knew that was what it was.

Every time he saw her, or heard her, or thought about her, everything suddenly felt right, and he swore his heart would literally skip a beat. He'd never gone for that whole sappy lighter-than-air stuff, the stories about finding a magical, star-kissed, other-side-of-a-rainbow kind of love... and yet here he was, lovestruck. He might as well have cartoon hearts in his eyes.

(Actually, he wasn't completely sure he didn't have cartoon hearts in his eyes. Apparently that was also a thing that could happen here. Best be extra careful, just in case.)

Well, he hoped he was hiding his true feelings for Applejack a little better than that, because neither of them was ready for the rest of the Apple family to know they were a couple. They had their reasons. For starters, neither AJ or Matt had any idea how others would react to an inter-species relationship, especially a physical one. Moreover, it was very important to Applejack that she not mess up the delicate balance of mutual respect and tradition in the family, and it was equally important to Matt that Big Mac wouldn't kick his ass.

(Truth be told, Matt was pretty scared of Granny Smith too; sure she might be a doddering octogenarian, but she also had a piercing look that seemed to see right through everything and which made Matt feel small and humble whenever he asked for another slice of pie, never mind this. Plus, she owned a thousand acres of farmland and a lot of shovels, so... no.)

Still, it wasn't enough for Matt, and it wasn't enough for AJ. They were a couple now, but you'd hardly know it when they were forced to spend most of their time pretending to be just friends, hoping nobody noticed the customary Equestrian "best friend" hugs were going on a bit longer than usual, and with rather more nuzzling than was traditional. Once, while saying goodnight on the farmhouse porch, he'd even found himself absent-mindedly stroking her coat, hands heading for new places, before a weak-kneed Applejack loudly cleared her throat and he snapped back to his senses. He wasn't sure if Granny saw; he hoped he could just pass it off as a human thing.

(It wasn't a human thing.)

But things couldn't stay like this. Sure, acting like a pair of giggly teenagers for the first few days had been kind of fun, exciting even: hiding behind barns and around corners for a quick kiss before straightening hats and hair and emerging nonchalantly like nothing had happened, making goo-goo eyes at each other over the dinner table while Apple Bloom was rambling on about her latest ideas on how to get her cutie mark. Now, though, the whole sneaking around thing was starting to get a bit old.

Neither Matt nor Applejack had actually said it out loud, but they were both wondering the same thing: "What happens next?"

Finding the answer would turn out to be quite the adventure.

Author's Note:

Thanks to MaxBeezy for not minding me borrowing his characters, story, and, um, everything.