The Shipping Files

by Damocles23

First published

Collection of shipping stories and cuteness galore.

Two couples.
Four Ponies.
Just one special day but still more than enough.
Crazy adventures and misunderstandings abound but when love is on a pony's side where's the worry?
A collection of intertwined narrative written by the Odd Pair of FimFiction, Damocles23 and SerenityViewer.
Cover art and general editing by SerenityViewer.

Hearts, Hooves and Hardships (by Damocles23)

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Hearts, Hooves and Hardships

by Damocles23


The blue pegasus fled across Ponyville’s skies and the pink pony followed.

She skipped and hopped the lenghy of the town streets with a look of absolute bliss, holding an envelope in her mouth with vibrant red hearts plastered on it. Pinkie Pie kept her eyes closed as she waltzed with absolute grace through the crowded streets, dodging everything from tables to ponies, as if she were in the most surreal obstacle course of the world.

The pegasus, on the other hoof, flapped her wings as hard as possible and threw frantic glances over her shoulder, only to see the relentless party pony continuing her constant chase, so far and yet so close to the rainbow maned mare.

Rainbow had very little hope of outrunning her. Or hiding from her for that matter. Defeat wasn’t an option this time, though. It wasn’t a silly game of hide and seek that the two played: it was a battle and their hearts were at stake...but Rainbow Dash cared far, far more about her friend’s heart than hers.

Rainbow Dash gave particular attention to the object that the pink pony carried in her mouth, mostly because that it felt for the pegasus almost like a metaphorical sword of Hooficles dangling over her head and over their friendship.

It was for her, intended only for her. Rainbow Dash couldn’t allow it.

It was, in fact, Hearts and Hooves day and Rainbow Dash didn’t want anything to change.

Especially not what Rainbow Dash and Pinkie Pie had.


“Oh, Bonnie!” the bright green unicorn chirped with glee. She eyed enthusiastically the humongous chocolate milkshake with whipped cream topping in front of her. “This looks so delicious.”

“Happy Heart and Hooves day,” said Bon-Bon, beaming at her fillyfriend and pushing the glass toward her, complete with the craziest, multi-coloured straw bits could buy. It amused Bon Bon to see her fillyfriend her usual cheerful self, especially after that crazy pink pony almost knocked over their table and the two along with it. It was one of the risks of opening a cafè outdoors in a village with a three-to-one ratio of weirdos...

“This is so great, you’re the best fillyfriend ever!” Lyra licked her lips and rubbed her hooves together with a content look.

Bon-Bon just waved a hoof at her.

“For something so small? You’re easy to please,” she giggled. “Come on, give it a taste.”

“The smallest things are the best, after all.”

The unicorn was about to bring the straw to her lips when, suddenly, the milk wasn’t the only thing shaken, but also the glass and the table, too.

A primordial terror grasped Lyra’s Heartstring’s heart and she could picture clearly a disaster of cream and chocolate spilled on the floor and on her coat. The table shaked faster and faster, its wooden legs drumming and rattling against the grass.

“What. The. Hay,” Bob Bon calmly said, bending her head low. Something flashed before her eyes: a chubby, pink silhouette that kept growing and growing larger under the table, threatening to burst out from under it...

Fortunately, it suddenly stopped just as fast, and both ponies sighed in relief.

“Phew.” Bon Bon wiped away a drop of cold sweat. “That was weird, but I’m glad it was noth—”

HellohaveyouseenRainbowDash?!” The pink pony appeared from thin air right behind Bon Bon, so close to her face that it startled a shriek out of her. Bon Bon lashed out a hoof in front of her, hitting the glass and sending it flying right on top of Lyra’s head, a curtain of chocolate and cream falling on her golden eyes.

Bon Bon realized she had never hated the pink pony more than in that moment. Her left hoof trembled, ready to land on that bubbly, feigning-innocence, face.

“No. We. Haven’t.” She ground her teeth. “Good day.”

“Shoot! I really need to give her this card or this Hearts and Hooves could be the worst day ever! The worst!” Pinkie hopped away from the two while placing the small envelope covered in red hearts back into her saddlebag. “Do you have any idea what could happen if she doesn’t get this card?”

Bon Bon wasn’t some kind of genius, but being Hearts and Hooves day she could’ve bet her left foreleg on what she was prattling about, but her mind had only one concern: her chocolate dripping fillyfriend. Lyra tried to babble something, but all she could do was stick out her trembling lower lip.

Bon Bon tried to turn and yell every profanity in the dictionary at the pink monster, only to find she had disappeared as fast as she had showed up.

A sack full of bits flew onto on the table, a pair of blue eyes in the distance flashed a contrite look and silently gave her regards to the couple.

“Well…” The rage in Bon Bon’s heart quelled when she saw her fillyfriend going from the verge of tears to wearing her usual, kind smile, even if still covered in chocolate. “It was about time for those two.”

“Can we get a bigger one?” Lyra gave a full toothed grin.

***

Rarity knew her mannequins just like real ponies. Not because of sentimental value or some kind of creepy obsession with lifeless plastic forgeries of real ponies, but because tending a business meant knowing every bit of her environment. Her boutique was an ecosystem of its own, and all of its parts, from the tiniest needle to the largest fabric lying around, were necessary, neigh, vital to the very life of her business.

That’s why a blue pegasus barely breathing and frozen on the spot, trying with very little success to pass as one of them was out of place, indeed.

Rainbow Dash kept a strained grin as she stood there in the most gracious pose, a mishmash of dresses strewn all over her coat, taken from the dozens laying around. Her mane was stuffed with freshly picked flowers, taken from some unfortunate shrubbery outside, destroying in the process the last few shreds of dignity the pegasus had left.

For a second, Rarity wanted to wait just a couple minutes more, just to see for how long Rainbow would continue this act and even if she would stay in her place if Rarity just spun around and closed shop. Of course, apart from being a mean spirited act, the ecosystem of her shop would be greatly compromised.

“Rainbow Dash.” Rarity tapped the floor with a hoof and spoke very calmly. Almost eerily. “While I am delighted to see you as always, you could have at least knocked. Also, those clothes don’t go well with your complexion or with anything else for that matter, all piled up together like that.”

Rainbow sighed and collapsed like a pile of jelly, shaking off from herself the various rags, changing her collected appearance to relief, although it quickly morphed into a frown. “Augh! Thank Celestia, I really couldn’t stand it any longer. Sorry for, well, the whole sham but I really needed a safe place and the door was open, you know.”

“Well, at least it was a friend rather than a burglar.” The unicorn used a whisp of magic to remove a solitary scarf hanging from one of Dash’s wings. “One thinks closing the door and completing one commission would last not even a minute...But I digress. Why would you need a safe place?”

“I need to hide from Pinkie Pie or I will break her heart.”

Rarity blinked. “Start from the, well, the start, darling.”

“It all began with a big flaming rock that would soon become our planet, give or take some millennia—” Rarity glared at her, drawing a sheepish grin from the pegasus mare. “You may have noticed that it’s Hearts and Hooves day.”

Rarity gasped, holding a hoof to her chest. “Really?! I thought that with the perfect weather, the piquant smell of love in the air and all the loving couples around, Heartwarming’s Eve came sooner this year!” She grinned and fluttered her eyelashes, enjoying the eye-roll from Rainbow that was so hard she half-expected her eyeballs to fall to the floor.

“Very funny. The thing is, since I’m not part of any of those loving couples, once I finished work I just wanted to take a nap until BAM!” Dash slammed her forehooves together to drive the point home, following it with a small grunt of pain. “Pinkie Pie finds me—”

“Well, you’re not that hard to find. Also if that girl wants to find somepony, she finds somepony.” Rarity shuddered. “Even in your house, in the marketplace, even when you’re under the shower and—”

“...With a Hearts and Hooves day card clutched in her mouth.”

“Oh.” Rarity’s pupils widened and her mouth formed a perfect ‘O’ of the most perfect stupor. “That is just adorable! Tell me what happened next! No, wait!” Rarity trotted away under the befuddled pegasus’ eyes and whipped a bottle of wine from a nearby drawer complete with a chalice. Positioning one of her chaise lounges—the one with the ruby-red cushions—closer to Rainbow, she laid down upon it and made one last, minute-detail adjustment to her mane.

“Now you can tell me what happened.” She poured a drink with a telekinetic blue hue and started sipping, staring and pleading with her eyes to Dash to continue.

“Well, I said that there was something big and scary behind her and I ran away when she wasn’t looking.”

Rarity stopped and spat the wine out, soaking Rainbow’s face. “YOU DID WHAT?” she roared in righteous fury as she ground her teeth and glared, closing the distance toward the pegasus’s forehead so fast that Dash could already feel the dangerous glow of a magical discharge gathering in Rarity’s horn.

“Before you rip my head off just let me tell you that I had very good reasons!” Rainbow took a few steps back and nervously longed at the exit.

“And what would they be? I bet the poor dear was in tears when she couldn’t find you!”

“Actually, she laughed it off and just kept searching for me. That's why I was hiding at your place. She found me in the sky, on the ground, in the school, inside Applejack’s barn, in a hole in the ground that I think Scoots and her friends dug but don’t ask me why—”

“But why, in Celestia’s name, are you hiding from her? It’s just a card. A Hearts and Hooves Day card never changed a world.”

“What if it’s something more? I mean, what if she really likes me?” Rainbow blushed, looking for a split second...girly? Was it possible to describe Rainbow Dash with that word?

“Well, that wouldn’t be so bad, right? I’m not here to tell you how to live your life, nor trying to be some improbable matchmaker, but Pinkie Pie is...not somepony you’d want to avoid for such a reason. Maybe just give her a chance?”

“Ah! Yeah, she’s so amazing I could totally...” A smile brightened Rainbow’s face. A real smile, not the uncouth and smug grin she always flashed in public, but something that reflected happiness, peace of mind, and sheer calm. It was as if the storm of adrenaline and pride in the pegasus’ heart had decided to stop for a brief moment.

“She’s so funny and really cute and thinks I’m the coolest thing since sliced bread, not that that's the main reason. She makes me laugh, makes everypony laugh! She’s just great.”

“Oh. So you admire her, then.” Rarity never saw Rainbow Dash baring her heart, especially not with her. The two were close friends, just as anypony else in their little group, but talking about their feelings with each other? Rarity was intelligent enough to know that it was something that would’ve never occurred—until that day, that is. Talking of somepony else in such a complimentary way, even! A pony that wasn’t herself for a change.

Rarity started to think that the serious part of that ‘something serious’ Dash had mentioned was already in motion...in Rainbow’s heart.

“Yeah! She’s just like a passage that I read once in a sappy book. It’s like...You know that everyday I go up and sweep the clouds away, so everypony else can have a sunny day. She does the same with the clouds right here.” She pointed at her blue chest, creating a small circle on her heart with the hoof. “Don’t tell anypony I ever said that,” she grumbled, even though her girlish blush survived. Rarity cracked a small smile.

“Your secret is safe with me, darling. But there’s something missing: if you hold Pinkie in such a high regard...Why are you so scared?”

“I’m not scared,” Dash scoffed, avoiding Rarity’s gaze. “It’s just that if there is something serious and I mean serious between us and things just don’t work out and I lose her.” Dash sat on her rump and sighed, burying her stare into the ground. “I would lose a friend and get a fillyfriend in the best case scenario...and lose them both if something goes wrong. Scratch the ‘if’: it will go wrong.”

Rarity arched an eyebrow and shook her head. “You don’t know that.”

“I can’t take that chance. That’s why I can’t do this to her. I’ll just have to hide until the day is over. You can close the shop with me inside if you want.” Rainbow picked up a fancy purple beret and put it on her head. “Just leave me the key...and maybe this hat."

“You should give her—No. You should give you two a chance.”

Rarity’s words went unheard as Rainbow was far too focused on reprising her sham and looking at the mirror. That was when Rarity thought the unthinkable and saw the problem from a different perspective.

“You’re the problem,” she whispered, her gaze lost in the metaphorical abyss, still astonished by the truth she had uncovered even when Dash jumped in front of her, outraged.

“What?! W-what does that mean?”

“Now I get it. You said ‘I can’t do this to her.' You’re not concerned about what she feels for you: You are the one who fears screwing up. You and you alone.”

“Oh, that was awesome. Good job, Shertrot Haylmes!” Dash clapped her hooves, dripping with so much sarcasm that the shop could have exploded for the sheer quantity of it had the window not been open. “After you’ve deduced this astonishing truth, what’s your plan now?”

“My plan? Mare up and at least talk to her! And I’ll tell you what's more—you should cut loose, go to her and smo—”

The sudden knock at the door made Rarity realize that she was really going overboard this time. The kissing part should always begin from the third date onward. “Just you wait a moment and don’t even think of fleeing out of the window.”

Rarity trotted away, still keeping her threatening glare on Rainbow Dash, and opened the door. Who she saw standing there, on her doorstep, brought a smile to her face. All things happen for a reason, she thought.

The brightest pink was at her doorstep.

“Hi, Rarity!” Pinkie Pie chirped and waggled her tail.

“Darling! We were just talking about you!”

“We?” Pinkie coked an eyebrow and giggled, glancing behind the unicorn at the tragically empty boutique. “Are you using the Royal We? There isn’t anypony here.”

Rarity turned her head and saw no trace of the blue pegasus in the room, only a gust of wind wafting the curtains of her window. She smacked her forehead with a hoof and kept a strained smile, lamenting her ingenuity in believing the fastest flyer in Equestria wouldn’t disappear the second she took her eyes off her. “Y-yes. We all have the right to do something silly once in a while…”

“You tell me! Next time you want to play the Queen I can be your High Chamberlain! Not that I have the time now. I really, really need to find Rainbow Dash. Have you seen her? I lost sight of her because Big Mac was dragging around a house.”

For some reason, Rarity didn’t react with more than a raised eyebrow at the Big Mac part. Maybe she was finally accustomed to Ponyville’s madness after a whole lifetime spent living there. But there was another, more urgent, problem: what to tell Pinkie Pie?

Rainbow Dash’s reasons, even if flawed, had some foundation and her intentions were pure. She admired in some ways the maturity she showed: how many ponies are strong enough to relinquish their personal happiness for the sake of the pony they cared so much? Very few...painfully so.

On the other hoof, she didn’t want to lie to Pinkie. The poor dear didn’t deserve this, on top of having her beloved constantly slip from her hooves and on a day when everypony deserved a small crumb of happiness. What, was she supposed to choose between her two friends?

Never.

If Rainbow didn’t want to give the pair one measly chance, then the Element of Generosity would provide—or at least give a little, tiny, subtle nudge in the right direction. The right one for the both of them, of course.

“She went out the window! Follow her! Go to her! Do what you must before it’s too late!” Rarity yelled and flailed her forelegs about, pointing toward the scene of the crime, so to speak.

Pinkie blinked and followed Rarity’s hoof in the direction of the fugitive pegasus. “Thank you, Rarity!” she bid her regards and ran out the window, disappearing in the distance. “Dashie! I need you right now! Come here!”

Rarity’s chest swelled with pride and hoped that at the end of the day Rainbow and Pinkie would get some happiness.

Her ears twitched when she felt a loud, rustling sound coming from outside her door. She leaned her head outside only to widen her pupils at the sight of Big Macintosh skipping on his merry way... dragging behind him an entire house to the horror and surprise of the fleeing citizens, including Rarity herself.

She slammed the door and shrugged. “Where did I put the wine?”

***

The Sun was slipping away, down into the horizon, and so were Rainbow Dash’s options.

She was hiding, sitting on a rough tree branch that bit into her rump. Her wings were raised, pathetically shielding her from the rest of the world and especially from a pair of blue eyes that she knew all too well. The prettiest one Dash had ever seen, even prettier than the sunset sprawling before her…

“I like Pinkie Pie.”

Saying those words, making a thought that raced across her brain like a bullet, eased the burden on her chest. Why couldn’t she live with this truth that made her so happy?

The sound of hoofsteps, no, hoof hopping approached and Rainbow gulped, knowing that it was time to mare up once and for all. No more running, no more turning into a nervous wreck. She owed herself at least some dignity and she owed it to herself to look in those beautiful eyes without fear.

“I guess you found me.” Rainbow sighed. “You always do.”

The hopping stopped. Pinkie just stood there, silent.

“I was tired, anyway. I mean, what’s the point? I just wasted an entire day, a special day mind you, just because you were trying to be nice to me. A day that I would have loved to spend with you…” She only whispered the last part, unsure if Pinkie or anypony else had heard it.

“You’re so nice to me, no matter what I do...That’s what boggles my mind the most and just makes it so difficult.” Rainbow saw from the corner of her eye Pinkie Pie still standing there with the same adorable, puzzled look. The card was still in her mouth even if its owner was lost in confusion. “Do you think it was easy for me? It wasn’t. I couldn’t do this to me—to us for any longer. Not to—” A whole slew of things to say knocked at the door to her heart, but they all meant the same thing: My special somepony. That’s what she had to say, but the uncertainty of the future choked her throat.

“...My best friend.” It was the only thing that she allowed herself to say. But you don’t want just that, right Dash? she thought, but no answer came. Not when it was so obvious.

Dash hopped down from the tree and safely landed on the green grass, staring at the blades growing from the ground, still without the courage to look her in the eyes. “I think it’s time to stop running away. Not from you! I’m tired of this game and I can only hope you’re not angry and that big heart of yours still has a place for me. I want you to know that I’m—

“A big featherhead!” Pinkie giggled as she finally took out the card from the envelope. Dash’s face drained of all color, her wings deflated and the image of a winged lightning bolt flashed through her brain.

“P-Pinkie? is that—”

“First Row seats for the annual Wonderbolts show in Las Pegasus, Saddlers Palace!” Pinkie placed it in Rainbow’s still unmoving hooves.

“But how…? How did you—”

“You left it at my place when I had that party last month. I don’t remember the occasion, but who cares? A party is a party!”

“Ah...That’s why I couldn’t find it, but I thought it was still at home and…” In her effort to avoid Pinkie Pie, Dash realized she had flat out forgotten the most valuable thing she had ever laid her hooves on.

“Well, at least you had a friend that took care of it. You told me that you had to stay in line for an entire day and you weren’t even sure that dealer wasn't a complete tout, but look at it! It even has the hologram. Completely authentic. “

"I wouldn't have left this at your place...unless—”

“Unless I had my party the same day you came back to get the ticket, silly!” she pinched Rainbow’s cheek with the most affectionate chortle. “Everything happens for a reason and the reason I had that party was probably because my friend Dashie needed to rest a bit. And your good friend Pinkie Pie noticed there was something shiny and forgotten on my bedside and here I am! "

"W-why the envelope, though? You know, with the hearts and all—"

"I just had that one laying in my drawer, somewhere. Aren’t you happy?”

“T-totally, Pinkie. Thank you.” Rainbow was happy of course, but not quite as she should have. No reasons to fear anything, her Wonderbolts ticket clutched in her hooves, the status quo left unchanged, just as Rainbow wanted. If this was a book, she thought, it would be a disappointing resolution at least…

“You’re welcome, Dashie. But next time you want to play Hide and Seek tell me first!” Pinkie Pie patted her friend’s back and turned her tail, happily hopping the way she came from with a smile on her face and a trademark giggle.

“Pinkie!” Rainbow called her out, stopping the pink pony in mid air. “You do know what day it is, right?”

She slightly tilted her head, confused. “It’s Heart and Hooves day, why?”

“N-nothing…” The last farcical, hilarious twist the story needed. “Thanks again.”

“You’re my best friend, too.” Pinkie blinked and reprised her hopping while Dash stood there, watching her friend turning into a small, jumping pink dot in the distance.

So that was it.

Rainbow Dash still had a friend and there was nothing to fear all along. Pinkie Pie was still the wonderful mare Dash had always known and she has lost an entire day just to give Dash back something she cherished so much, asking for nothing in return but her smile.

That would be a disappointing end to the day and the story...but neither of them was over yet. Dash smirked and decided she would be the one to write a better ending. The one that Pinkie deserved more than anything.

“I hope the shops are still open.”

***

Pinkie Pie sat at the Cafè, lonely and sticking out like a sore hoof amidst all the couples that waited to end the day in each other’s embrace, just as Luna’s milky moon lit the first hours of the night. She didn’t mind being alone, though, because when she was surrounded by so much happiness she couldn’t help but feel happy as well.

She saw Lyra and Bon Bon going about an evening stroll, who to her delight waved at her...well, only Lyra actually, who goaded her fillyfriend into doing it as well. Pinkie didn’t mind: she was just happy to not having ruined their day a few hours ago.

She saw Derpy and her doctor friend, still the epitome of the perfect gentlecolt, but painfully awkward and timid around a mare. His cheeks were so red after Derpy entangled his hoof with her own that Pinkie feared he would burst into flames.

Even that Sweet Apple Acres farmhoof, Caramel she thought his name was, enjoyed a pleasant evening with a sweet mare.

She didn’t mind being alone. All of the day spent chasing after Dashie was like passing it with her, from a certain point of view. But maybe she should have asked to spend this evening with her, after all. It was far more enjoyable to spend time with a pony that stood still and even better when that pony was Dashie.

A special day is not very special if not passed with one’s best friend…maybe something more, even.

I would have loved to spend it with you…

Did Rainbow Dash really say that or was it just a silly daydream? No. She totally said it...and not seeing her wonderful friend at her side hurt.

“I would have loved spending it with you, too…” she whispered as she felt something warm escape her eye and rile up her cheek.

She sighed and lamented on how ‘gloomy’ she was getting and took another sip of her juice. Maybe one day she will talk with her about the silly little things she thought once and they’ll both laugh. They had so many days of their life to spend together, so why think so hard about this one on which the Sun had already long set?

That’s when she heard a flutter of wings right beside her and a tiny shadow covering a patch of Luna’s Moon. The blue pegasus landed next to her, hardly making a sound, and she saw Rainbow Dash holding a small envelope, covered with red hearts, clutched in her tender smile. She didn’t even have the time to say ‘Hi’ when the pegasus offered it to Pinkie, much to her amazement, and a whole stream of those wet, warm things twinkled out from her eyes.

She felt something warm in her chest that kept growing and growing the longer she kept her eyes on that adorable blue daredevil.

Hearts and Hooves day...The very meaning of it just flew over her head and Dashie had to be the one to remind her.

“Will you be my special somepony on this special day?” Dash said.

She threw herself in an embrace and cried ‘YES’ until tears were crossing her smile.