The Mischievous Matchmaker

by Painbow Bash

Rating: teen
Tags: Discord, Pinkie Pie, Main 6, My Little Pony: Friendship is Magic, Comedy, Romance, Random
Length: 4606

Discord heads to ponyville for some fun. While there Pinkie convinces him to help her prank her friends. Hilarity, chaos, and (you guessed it) shipping ensuses.

WARNING contains needless fun, jokes, adorableness and best of all, shipping (not between Pinkie and Discord).
Not for the faint of heart or those who like devastatingly sad fics, this is a light hearted fun fic and should not be taken seriously. If laughter and happiness continue of longer then a period three days consult a certified physician and tell him to read it too.

Now that the disclaimers are out of the way, this is a fic about Discord going on a pranking spree with Pinkie Pie, along they way she convinces him to help out her friends with various problems or dreams in the form of pranks one of which being to set up AJ and RD, this story is not focused on Appledash, but it does contain it. Proofread by SweetieB0T.

Published 2014-02-03 10:40:02 UTC
Last updated 2014-02-03 10:40:02 UTC

A rude awakening

It was a beautiful day in Ponyville, a bright clear crisp day without a cloud in sight, the perfect weather for doing some manual labor, reading the newest edition of Daring Do, showing off a dazzling new ensemble around town, taking a nap in your favorite tree or best of all playing a few harmless pranks on some unsuspecting victims. The latter is the day plan for a certain bubblegum colored mare, who was at the moment currently asleep in the loft of the village's main confectionary shop, dreaming literally sweet dreams about creamy frosting and other such things, in a bed with enough stuffed animals to smother a dragon. Beside the bed there happened to be a nightstand with several empty glasses of various sugary punches, sodas and other such similar drinks. Among the items on the nightstand there happened to be a large parcel wired to an alarm clock, but unbeknownst to the ponies peacefully going about their business below, that particular package held quite a volatile payload, and it was almost time for its explosive awakening.

In another part of Equestria, The royal Canterlot palace to be exact, there sat a dejected creature, who was more akin to some horrible cotton candy machine accident than a actual animal, but regardless there he sat wondering when he let himself get so drab and boring, cooped up in places he would rather not be in, waiting to be called upon like some maid to clean up whatever mess that his "friends" couldn't handle.

"There's only one thing for it." He said to no one in particular.

"I'll just have to take a vacation to somewhere a little less stuffy and uptight, it will be good for me, not to mention for ol' Sunbutt."

And with that he was off in a puff of smoke. Elsewhere in the castle a very irate princess was combing cotton candy swabs soaked in chocolate milk out of her mane and tail muttering to herself.

"If I ever get my hooves you Discord I swear I'll send you to the moon for the rest of your endless life."

Back in Ponyville Pinkie woke up rubbing the sleep from her eyes and letting out a yawn at the same time. Looking around the room she noticed the package, her eyes went

wide and she barely had time to shout;

"Omigosh its!" before the package detonated.

Under the bedroom, in the kitchen of Sugarcube Corner, Mrs. Cake was in the process of mixing some batter when without warning there came from up the stairs a loud POP! Spilling batter all over herself, she ran upstairs to see whether Pinkie had finally gone and blown the roof up, instead what met the middle aged mare left her jaw hanging at the messiest sight she had ever witnessed.

A few seconds earlier over a little ways in the town market stood Discord, arguing with a large red stallion about the price of apples, just for the fun of it.

"Two bits for apples is outrageous, why with hundreds of trees and only four ponies to split all that money between I think you can more than afford one bit for apples." Discord said with a smirk, unknown to Discord, Big Mac had an education under his belt and

excelled at math.

"Nope, don't try to muddle the matter with your ridiculous mathematics, the price is two bits."

"Bah! You are no fun at all, isn't there anypony who is up for some fun in this town?" Then almost as if on queue a loud POP! caught Discord's attention.

"What... who.... how....." was all Mrs. Cake could stammer as she looked around the walls and ceiling of her once beautiful loft.

"Oh! Hi Mrs. Cake! how do you like my special event alarm clock?" Chirped Pinkie unaware of the many emotions Mrs. Cake was feeling right now.

Glancing around at the confetti and streamers plastered to every surface she barely contained a shoutyell of anger.

"I suppose I should be used to it by now" muttered Mrs. Cake under her breath. Trying to get the state of the room off her mind she asked dryly: "Well what is the occasion today Pinkie?"

"I'm glad you asked, its prank day!" said Pinkie enthusiastically.

"Oooh! That sounds like fun!" said a third party entering from a door in the wall of the third floor that wasn't there before, it was Discord, who was happy that he finally found something fun to do. Mrs. Cake however was not so happy, in fact the sight of Discord walking into the room from the third floor window was too much for her, as such she just quietly walked backwards out of the room as if she had never seen him enter. She decided it would be better to claim to have not seen nor heard of him at all until he left.

"Oh hi Discord! what brings you here?" Asked Pinkie.

"You know how it is, o was in the neighborhood and decided to see if you had anything fun planned for today that you might want help with." He said, trying to look as innocent as possible.

"Well you sure have some good timing, I was just about to go pranking by my self since Rainbow Dash is helping AJ today with her apple orchard. Buuuuut now that you're here I happen to have a free space, if you want to help me?" said Pinkie with a knowing smile on her face.

"I would be delighted to help you pull one over on your friends." Discord said almost endearingly.

"Great! with you here we can do some super-duper-duper pranks! and I know just how to pull them off." Said Pinkie with a hint of mischief in her voice.

Author's Note

Heya guys, this is my first fic so if any of the formatting or anything is off I apologize im still getting used to it, any comments or constructive criticism is very welcomed, and don't worry it gets better. Hope you will enjoy it!

"Harmless" fun

Twilight sat in her library quietly thinking to herself about the latest study she had undertaken, which happened to be about her feathery pet Owlicious. At the moment she was sitting on a overly stuffed throw pillow which she used as a chair by her desk, next to the lavender mare was her aforementioned pet sleeping on his stand dreaming of mice bunnies and other such things that owls like to snack on. Twilight herself was on the verge of sleep with exhaustion trying to figure out her latest conundrum

“Does he actually understand us and hoot on cue to be funny, or is he just hooting whenever we talk in his general direction?” mused Twilight out loud.

“I wish I could figure out which it is, it would be great to be able to talk to Owlicious, ah well maybe later right now I'm far too tired.” she said with a long yawn, and with that she trotted off to bed.

Unknown to Twilight her musings were heard by someone, two someones to be exact both of whom were hiding in the shrubbery that surrounded part of her home.

“Oh oh oh! I have an idea” said Pinkie in a excited but hushed voice.

“How about we help Twilight and our friends with their problems while pranking them?”

“What? I don't see how that will be very fun.” Replied Discord.

“If we help Twilight solve her current study by sayyyy swapping her and Owlicious’ bodies it will be good for Twi because she will get her research done and be a hoot to watch at the same time! She will also probably be less angry at you later if you helped her with this problem of hers.” Said Pinkie practically beaming.

“Say turning a princess into an owl does sound like a great fun, oh and Pinkie.”

“Yeah?”

“A hoot, really?”

“Hey I thought it was pretty funny.” Replied the bubbly pink mare with a slight laugh.

“Well lets sit back and watch the fireworks.” Discord said with a snap of his fingers.

Twilight awoke groggily as one might who was interrupted from a much needed nap. She went to rub the sleep from her eyes but what she found instead of a hoof was a feathery appendage.

“What! Where did this come from, where are my hooves!” She thought frantically.

“It seems like I’m not me at all, I have to find a mirror.”

She went to take a step and instead found herself falling a couple of feet to the ground.

“Oof! How did I get here, this is Owlicious’ stand not my bed!” Then it dawned on her, she comically pushed herself up with her wings and on to her now taloned feet. She would have probably screamed if she could have, instead all that came out was a long high pitched hoot.

“I’m in Owlicious’ body! But wait if I’m here that means…” She didn't have time to finish her thought for at that moment she saw her body fall headlong down the stairs and land clumsy on the floor.

“Oh no, this is bad.” However it only got worse, she watched dumbly as her body stumbled across the floor and out the open window, and kept on half flying half tripping moving farther and farther away.

“Great, just great now i have to keep myself, or Owlicious i guess, from not only embarrassing me but also from ruining my body!” She thought to herself, and with that she flew about as gracefully as Rainbow Dash after her fifth mug of cider, out the window and after her body.

Behind her in the bushes Discord and Pinkie sat ready to burst with laughter, once Twilight had flown after her body they both laughed so hard they thought that they would’ve popped a lung. Once the duo calmed down a bit Discord said to Pinkie;

“You were right Pinkie my dear friend, that was a hoot indeed!”

“I told you it would be good.” replied Pinkie with a little laugh still in her voice.

“Now on to Rarity’s I have a great idea of how to make her let her mane down and get a little dirty.” Discord simply smirked and raised an eyebrow.

“No not like that silly!” yelped Pinkie a bit defensively realizing how what she said had sounded.

“Well maybe a little like that, just a tad.” Discord only smiled a bit wider and asked;

“Well how are we to pull off this completely innocent prank then?”

“We only need one thing, or guy i guess would be the correct term.” At this Discord leaned in and listened to the bubble pink mare’s plan, his smile widening all the time.

Over in Carousel Boutique Rarity sat reading her latest romance novel (a particularly good one about how an innocent prank reveals unknown feelings between two friends) next to her younger sister who was trying to figure out some lyrics to a song she was writing at the moment. Rarity was interrupted from her engrossing read when there was a heavy knock at her door.

“I’m sorry but we’re closed today, you are more then welcome to come back tomorrow though.” She said trotting to and opening the door, however what she saw made her stop dead in her tracks. There, right outside her door was an all too familiar rock, a dark grey nightmare, that which haunted many of Rarity's dreams, Tom.

“Heya baby long time no see.” Said Tom in a gravelly voice. Rarity on the other hand just shrieked and slammed the door.

“How is this possible!” she cried to Sweetie Belle, who was completely oblivious to the whole situation.

“How is what possible Rarity?” Asked Sweetie Belle slightly afraid of whatever had unnerved her sister so, but more curious than anything else.

“Hey honey are you just gonna shut me out again? And here I thought I was the one with a heart of stone.” Called Tom though the door, much to the grievance of Rarity who was now thinking of ways to get rid of Tom without having to talk to, or look at that accursed rock again. Just then the door cracked just slightly enough to let a little bit of Tom peek through and say;

“HERE’S TOMMY!” Rarity nearly fainted right then and there, but she managed not to, instead she quickly told Sweetie Belle in a loud whisper;

“Go and borrow one of Mr. Drill Bit’s jackhammers, right now.” Sweetie Belle herself was quite confused by the order and the rock talking to her sister, but hearing the earnestness in Rarity's voice she ran off through the back door right away.

Over in the bushes Discord and Pinkie looked at each other a bit disappointedly.

“Well that was less fun than I thought it would be.” Said Pinkie looking at a rock pushed up against the door of Carousel Boutique.

“I agree.” said Discord rather unamused with what he thought was a perfect plan.

“lets go see if we can’t get some fun over at Fluttershy’s.” Said Pinkie, trying to think of a way to help and yet still prank Fluttershy.

“Ooh! I got it!” Exclaimed discord.

“You know how Fluttershy always wanted to be a tree right Pinkie?”

“Brilliant!” Exclaimed Pinkie, ready to pop with joy at the prospect of Fluttershy becoming a tree.

“Why it’s elementary my dear Pinkie.” Said Discord suddenly wearing a tweed Deerstalker hat, and smoking a bubble pipe.

Over at Fluttershy’s cottage Pinkie and Discord waited in the foliage for the timid mare to exit her house that they might have a full view of her reaction. The door to the cottage swung open suddenly and out from it bolter a small white bunny being pursued by none other than Fluttershy. Discord took aim with his fingers and firing a fake shot at the yellow Pegasus she was instantly rooted to the ground in a flash of light. Once the light was gone instead of Fluttershy there now stood a medium sized tree with what appeared to be a face on the middle of the trunk. Discord and Pinkie had to cover their mouths to avoid laughing at the spectacle before them, Fluttershy however was having the time of her life watching some birds fly over and nestle in her branches. What she failed to notice however was Harry the bear striding over to her. She noticed just in time to let out a small shriek before Harry put his back onto the tree and began to scratch himself by rubbing his back roughly against a very distraught tree. Pinkie and Discord sat there dumbstruck, trying to decide whether or not to help. They were quite surprised however to see Twilight run out of the forest and straight at Angel Bunny. At first they were both a bit confused, but after a owl fluttered after her they remembered that Twilight was not quite feeling herself at herself moment. And seeing her snatch up the aforementioned bunny in her mouth Pinkie leaned over to Discord and said:

“I think we might need to cut these two pranks a bit short.”

“Why? This is hilarious!” Said Discord hoping that Twilight’s body would finish her snack before he had to intervene.

“Because Fluttershy is being smothered by a bears posterior and Twilight is about to eat her favorite pet on top of that, you wouldn’t want to hurt Fluttershy that much would you?” Asked Pinkie knowing full well that Discord liked Fluttershy a bit more than the rest of her friends.

“Okay, fine.” And with that Discord snapped his fingers again and set things back in order. Twilight spat Angel out of her mouth and immediately shouted quite angrily:

“DISCORD!”

“I think she figured out how she and ol’ hooty swapped bodies.” Stated Pinkie.

“Tactical retreat?” Asked Discord.

“Roger that, lets check back with Rarity. She probably won’t teleport us to the moon, or worse yet, lecture us to death.”

“Yes lets do that.” Agreed Discord. With that said they both ran off to check on Rarity, and save their hides from Twilight’s wrath.

After Twilight had cooled down a bit she noticed Fluttershy standing next to her and said:

“Oh hi Fluttershy where did you come from?” Instead of answering Twilight's question she simply stated:

“I would not like to be a tree, ever.” And walked back into her house.

What Discord and Pinkie found when they arrived at Carousel Boutique both surprised and amused them, there, in Rarity’s front yard was none other than Sweetie Belle, Rarity and Tom, well most of Tom anyways. Sweetie Belle was sitting a few feet away from the other two looking quite confused, Rarity however was in the process of reducing Tom into a fine gravel, and guessing by the way her mouth was moving it was probably a good thing that the jackhammer that she was employing drowned out her voice. Pinkie leaned over to Discord and stated with a smirk:

“I told you this prank would rock.”

“Oh please spare me your bad jokes Pinkie, I can barely take this level of punishment.” Replied Discord smiling.

“Ow Discord that one just hurt. Well now we got three down, and two to go. And I know just how to pull it off.” Just the level of mischief in Pinkie’s voice was enough to let Discord know that this last prank would put all the others to shame.

Dead giveaway

Dead giveaway

The day was drawing to a close as Applejack bucked the last tree on her schedule. She watched the apples fall nicely into the large barrel that she had set at the base of the tree, then turning to her friend and at the moment fellow laborer she said:

“Well that should just about do it for today, after we load this last barrel into the barn how bout we get some of that cider I promised ya? She asked Rainbow Dash in her usual country accent as she wiped the sweat from her brow.

“Sounds like a plan!” Dash replied, fastening the lid onto the barrel full of apples that Applejack had just filled.

“I should tempt you with cider more often if it gets me this quality of work.” Joked the orange mare, balancing the barrel of apples on her back.

“It’s not the cider thats tempting me.” Thought Dash to herself.

“No prob AJ, I’m always glad to help you out.” She replied cheerily.

“Well lets get you your reward then Dashie.” Applejack mentally facehoofed as soon as the words had left her mouth.

“Consarn it! Why did i say Dashie? Maybe she didn’t notice it.” Applejack hoped to herself, but Dash had indeed noticed and was at the moment trying to decide what to make of it.

“She just called me Dashie! Maybe it was just a slip of the tongue. But what if it was intended?” The cerulean pegasus decided to press her luck and call AJ by a nickname of similar aptitude.

“Sounds like a plan Jackie!” Both ponies blushed at the pet names and awkward silence that followed enough that it was quite visible on their faces.

“Gah! How i wish I knew what AJ thought of me, I don’t want to risk our friendship on this, but if she does feel the same way how awesome would that be! Ugh I’m going to drive myself crazy trying to figure this out.” Little did Rainbow know that at that moment Applejack was had a very similar problem on her own mind.

“She just called me jackie! I hope that means what i think it might, if it does that would just be too amazing! But what if it doesn’t? Augh! This will be the death of me yet.” Applejack worried, wondering if she could ever work up the courage to just tell Rainbow how she felt.

Off a distance in the top of an apple tree sat Discord and Pinkie observing their final targets.

“You are quite right Pinkie my dear, they will never get anywhere going about like this. And since you insist on helping our friends how shall we both prank and ‘hook up’ your friends?” Asked Discord watching Applejack and Rainbow Dash through some opera glasses he had conjured to spy on their last victims for the day.

“With some good old fashioned terror and pressure!” Chirped Pinkie, she then leaned close to Discord and disclosed her grand plan. The entire time she described it to her cohort his smile ever widened with anticipation.

As Applejack was exiting the barn she saw something that caught her eye, it was a strange looking pony just meandering along in the middle of her orchid with a slight limp muttering to himself.

“Howdy partner whatcha doing here?” Applejack called out to the stranger, who continued on trotting around slowly as if he didn't hear her.

“Huh, maybe he didn’t hear me. Dash wanna help me see what this guy wants? I don’t really like the look of him.”

“Yeah me either, lets see what he wants so we can get away from Mr.weird Mc.creepy.” Dash and AJ walked over to the stranger who as they got closer to they noticed he wasn’t actually muttering but groaning as if in confusion and pain.

“Hey buddy are you alright?” Dash called out trying to get his attention as she landed a bit closer than intended, but she did get his attention, and no sooner had she then the shabby looking colt swung his arm with full force straight into Dash’s wing. AJ needed no further reason to buck the now violent stranger into next week, which she did. However what she did not intend to do was conclave his skull, which she also did.

“Celestia’s flaming flank! I didn’t mean to crush the varmint's head like that!”

“He only damaged my wing you didn’t have to kill him AJ!” Said Dash now very concerned about the body laying before them. No sooner had the words left her mouth then the body in question started crawling towards them now growling angrily. Dash hopped into AJ’s arms while both mares screamed.

“HOW THE BUCK IS HE ALIVE HIS HEAD IS ONLY HALF THERE!”

“HAY IF I KNOW DARLIN” Shouted AJ not noticing the now numerous strange looking ponies closing in, attracted by the all the commotion.

“AJ, I think i know why.” Said Dash hopping out of the farm mare’s arms and walking backward a bit.

“What's that sugar cube?” Asked Applejack with a faltering voice.

“Zomponies.”

“Normally I would say that you were full of it but right now….” AJ looked first at the bloody mess of a pony crawling towards them then to the other ragged ponies slowly closing in all around them. backing into the only safe place not blocked off by walking corpses, the barn. Dash followed AJ into the barn then rapidly shut and with Applejack's help barred the doors with some wood planks that were in the barn.

“Applejack, I don’t think we can get out of here.” Dash said with none of her usual upbeat tone in her voice.

“Can’t you fly us out?” Asked the orange pony with a bit of doubt in her voice, almost as if she didn’t think her own suggestion was valid.

“I could probably fly us high enough that we could avoid all the earth ponies, but I noticed a few pegasi in the hoard and I doubt i can outfly them with either you on my back or with this damaged wing.”

“I was afraid of that, what now?” Wondered AJ thinking of what they could possibly do. Dash however was thinking of what could have been, the Wonderbolts, her friends, and most forefront on her mind, Applejack.

“Why didn’t I ever work up the courage to tell you AJ? Well i guess it doesn’t matter now, heck i could just walk up and kiss her since it looks like im dieing in a minute anyway.” Even as Rainbow finished this line of thought hoofs came bursting through the door, revealing glimpses out at their grisly fate. Dash, now having made up her mind walked over to Applejack and said:

“Hey AJ there’s something I should have told you a long time ago. It doesn’t really matter now but what the heck.” With that said Dash just quickly leaned in towards AJ and planted her lips on her best friend’s. Time froze for both of them, there was no longer any zomponies raging at the doors, no barn not even the hay underneath their hoofs, all that mattered to both of them was this moment. To Dash's surprise and glee Applejack not only didn’t pull away but pressed harder into the kiss, savoring the sensation of the moment. Dash on the other hand was in pure ecstasy, loving every moment of what she later would call, the best decision she ever made. The kiss ended too soon for both of them, but one thing they both immediately noticed was that there was no sounds of growling or wood splintering, no holes in the walls or door, no bruise on Dash’s wing, no nothing, all of the barn looked as if it was never under attack in the first place.

“Something isn't right here.” Applejack said looking about the barn

“Really? I thought it was a great kiss.”

“That was a great kiss.” Applejack said losing her train of thought and smiling at Dash for a moment before getting her mind back on track.

“But I mean look at the walls and door, look at your wing, its all fixed nothings wrong. Almost like it was all a big joke.”

“Or prank…. Hey didn’t Big Mac say he saw Discord in town earlier today.” Asked the light blue mare with a knowing smirk on her face.

“Why that dirty low down varmint!” Spat Applejack looking back and forth as if she expected to see his smiling face taunting them.

“Well on the one hoof he did scare the hay out of us, but on the other hoof…..” Dash trailed off walking a bit closer and draping her wing over Applejack’s back.

“Well I guess I can forgive him this time.” AJ said nuzzling Dash and happily sighing into her embrace.

“Aww well isn’t that just down right adorable.” Observed Discord wiping away a tear from the corner of his eye.

“HA! I told you it would be amazing.” Said Pinkie with a smug grin on her face.

“Okay fine you were right Pinkie, that was both fun and helpful. Hey I wonder if I could do this all the time, you know to be of use out in the world like Celestia is always getting on about.”

“That is the BEST IDEA EVER! I mean, it's like all of my favorite things, pranks, fun and forcing ponies into relationships!” Shouted Pinkie jumping into the air like someone had just released a spring.

“Yes I do think it’s a smashing idea, not to mention tons of fun. Well Pinkie I thank you ever so much, and I hate to leave after all the fun we have had, but I know of a certain stuffy red stallion who needs to loosen up a bit, ta ta! And with that he left to go make some more romantic mischief.

Author's Note

Hey guys, hope you liked the fic, once again comments and critiques are welcomed!