Pinkie Pie: Matchmater Extraordinaire

by PrincessSparklesX

Rating: everyone
Tags: Slice of Life, Comedy
Length: 2018

Pinkie Pie has a brilliant plan; One that can't possibly fail: She's going to help her friends find their very special someponies! With help from her new sidekick, Spike, they're sure to help their friends find pure happiness. Right?

Pinkie Pie has come up with a lot of ridiculous ideas before, but this one really takes the cake. What is this new idea she's come up with? Why, she's playing matchmaker, of course! With some help from an unwilling Spike, she's going to make sure she finds to perfect somepony for her best friends!

That, or she'll turn the whole town upside down trying.

Published 1970-01-01 00:00:00 UTC
Last updated 2013-07-27 00:04:06 UTC

Pinkie's super duper amazingrific plan

“Uh, why do you need my help, again?” Spike asked with a tired yawn. He and a familiar pink party pony were currently sitting on some of the plush chairs in Sugarcube Corner. It was around dawn, so nopony would be there to interrupt them. Normally, Pinkie wouldn't be up this early, but she had a plan: A plan so brilliant, it couldn't possibly fail. A plan that needed to be top-secret, in order to make the outcome perfect. A plan that, if executed correctly, would make her friends happier than they had ever been. What was this plan, you might ask? Why, our beloved Pinkie Pie wants to help her friends find their very special someponies, of course!

“Because, silly, you seem to know the most about romance besides Rarity, and I couldn’t ask her to help me! If I did that, then she wouldn’t have the opportunity to find her perfect match!” Pinkie said with a slight giggle. "We also seem to think alike, which will be super helpful with finding a match!"

Spike gave a tired groan as he frowned at Pinkie. Dark circles formed under his eyes - the effect of Pinkie Pie sneaking into the library around midnight and waking Spike up. How she managed to do it without waking up Twilight was a mystery to Spike, but he was too tired to really delve down into reasoning at the moment. “And what about me?”

“What about you?” Pinkie asked, a goofy grin beginning to form on her face.

Spike opened his mouth to retort, but quickly closed it when he realized what he was about to say was both ridiculous and implausible. “Never mind...” he grumbled.

“Don’t be sad, Spikey-Wikey! I’m sure we can find somepony super special for you after we find our friends somepony special!” Pinkie said as she patted the dragon in question on the head. Spike lamely attempted to swat the pink mare’s hoof away, which caused her to giggle again.

"Yeah, yeah... I think I'm good for now. Let's just stick to your original plan."

Pinkie bounced in her seat and nodded enthusiastically. “Alright! Well, we have an entire town full of ponies for our friends! Some of them are super intelligent like Twilight, and some of them are super silly! They also have different mane styles, and body shapes! Ooh, and some of them have wings, and some of them have horns-"

"You're getting a little off-topic, Pinkie."

"Oops! Anyway, who do you think we should start with?”

“Uh... Fluttershy? Maybe?” Spike replied uncertainly.

Pinkie Pie jumped up in the seat she was in and let out a squeal. “Ooh, yeah! Fluttershy, totally! Maybe it’ll help her get over her shyness if she were to find a special somepony! Wouldn't it be neat if our Fluittershy came out of her shell? We'd be able to go more places with her, and do more fun things with her! It'd be awesome!”

“Right...” Spike muttered doubtfully, “You sure this is a good idea? What if we mess this whole thing up? Then what happens to our friendships? ...Pinkie?” He scrunched up his face in frustration when he realized Pinkie was too lost in her thoughts to listen to his blabbering.

“Which pony in town should we start with?!” Pinkie suddenly shouted. She leaned in towards Spike, her eyes widened with anticipation for his answer.

“Well... How about you give me a little personal space, first?” Spike chuckled uncomfortably as he pushed Pinkie back.

“Oopsie, sorry! I’m just super excited for this!” Pinkie replied as she sheepishly rubbed the back of her head.

Spike stared at her for a few moments, before shaking his head and averting his gaze to the book on the table in front of him. It was a rather large book, containing information and pictures of everypony in Ponyville. Pinkie Pie had made it herself, claiming it 'To be a guide for anypony who wants to know anypony in Ponyville!'. Of course, she initially had to get permission from every resident in Ponyville to make the book, which wasn't an easy task to acccomplish.

“Well, I was thinking that-”

“What about him?!” Pinkie asked excitedly as she pointed a pink hoof at a white Pegasus with a blonde mane. He had a rather strange body build - he was extremely muscular for a Pegasus, but his wings were as small as a filly's.

A frown formed on Spike’s face as memories of the pony popped into his head. The Pegasus Pinkie had suggested was quite loud and enthusiastic - definitely not something Fluttershy could handle. Spike quickly shook his head. “I don’t think he’s the one.”

“Hmm...” Pinkie tapped a hoof to her muzzle in thought. She flipped to the next page, her eyes scanning for potential matches for Fluttershy. She squinted, before pointing at a dark grey Pegasus pony with stunning golden eyes. “Him?”

“I’m not quite sure about him... Let’s add him the the ‘maybe’ list for now,” Spike replied as he briefly looked at Pinkie. “I thought you knew all of the ponies and their personalities?”

“Oh, I do!” Pinkie said, her eyes still focused on the book, “But Fluttershy is kind of a mystery, you know? There are some moments when she’s super shy, but there are others when she’s totally awesome and brave! I mean, I’m not trying to be a meanie pants or anything, but she can be a little odd that way.”

“...Look who’s talking.”

“Huh? Did you say something?” Pinkie looked up at Spike, who gave a nervous smile in return.

“Nope, not a thing!” he replied in an unconvincing tone.

Pinkie, being her normal and optimistic self, simply blinked before a huge grin spread across her face. “Okie dokie lokie!” Her eyes fixated back onto the book as she continued her search. “Ooh, what about him?” Pinkie asked again, this time pointing at a pony with a white coat dotted with brown spots.

“Uh... Pinkie?”

“Yeah?”

“That’s a colt.”

Love letters

"Okay, Spike, now that we've finally settled on a good match for Fluttershy, we need to write a couple of letters!" Pinkie gave the purple dragon a grin, who simply sat there with a dumbfounded look on his face.

"Why?" he simply asked.

Pinkie leaned against him and let out a squeal. "Because... that's how the plan works! We're going to set up dates by making it look like the other pony is asking them out! I think it would be easier than trying to convince them to go in person, you know?"

"I guess...?" Spike replied with a simple shrug, "Do you have some paper and quills?"

Pinkie Pie jumped up out of her seat and nodded. "Absolutely! I'll go get them!" she said happily, before quietly bouncing up the staircase that was behind the counter. Despite have a boundless amount of energy, Pinkie knew that there were going to be times when she needed to be quiet. The last thing she wanted was to wake up the babies.

Spike leaned back in his chair with an exasperated sigh, his gaze turning towards one of the windows. Celestia's beautiful sun was now rising over the horizon, a signal that it was almost time for the residents of Ponyville to wake up and start another day of work. He and Pinkie wouldn't have much time to write the letters and sneak them into the mailbox. "I have no idea what I've just gotten myself into."

"Oh my, what a beautiful day! What do you think, Angel?" Fluttershy asked as she opened he bedroom curtains. The white bunny Fluttershy had spoken to tentatively sat on her head impatiently, constantly poking her forehead with one of his paws to hurry her along. It was breakfast time for Angel - he didn't have time for idle chit-chat with his caretaker.

"Don't worry, I'll get on breakfast right away!" Fluttershy responded to the bunny as she trotted out of her bedroom and into the main room. The yellow Pegasus picked up the various bowls that were scattered around the room and began to fill them each with fresh vegetables from her garden.

"Okay everyone, breakfast!" Fluttershy quietly hollered. Although her voice wasn't the loudest, it was still enough to have all the animals come running into the room. She sat the bowls and smiled as all of her animal friends began to chow down on the vegetables.

It was then that she noticed Angel had hopped off her head, and was no where to be seen. She glanced around the cottage in confusion, before leaning towards the mice and quietly whispering, "Excuse me. I don't mean to interrupt or anything, but did you happen to see where Angel hopped to?"

A small, grey mouse looked up at her and nodded, pointing a paw in the direction of the door. After she thanked the mouse, Fluttershy quietly made her way to the door and peered outside. Angel bunny was currently standing next to the mailbox, staring at something that had fallen to the ground.

"Oh, Angel, there you are!" Fluttershy said with a smile as she opened the door completely and walked over to her friend. "Why, I was starting to get a little worried... I'm glad that you're okay, though!"

Angel rolled his eyes in response, before picking up the object on the ground and giving the letter to the pink-maned pony.

"Oh, that must be a letter! I wonder who it's from?" Fluttershy wondered aloud, but a small frown formed on her face when she realized there was no name or return address written on the envelope. Heck, there wasn't anything written on the envelope besides 'Fluttershy' written in fancy script.

After thoroughly checking to make sure she hadn't missed somepony's name, Fluttershy opened the envelope and pulled the letter out. Her eyes scanned the letter, particularly catching the words 'date', 'restaurant', and 'curious'. The Pegasus let out a squeak as she dropped the letter, quickly backing away before her rump hit the door.

Angel Bunny, however, made his way over to the letter and began to read it himself. An audible noise that sounded like laughter began to erupt from him, before he turned back to Fluttershy and pointed to the letter.

"C-can you believe it...? Oh, Angel, what do I do? I don't.... think I'm the dating type! I'm not really sociable with new ponies, and I don't think it would work well... The fact that it's a mystery pony just makes it worse! Oh, I don't really want to go, but at the same time... I don't really want to hurt anypony's feelings! What do I do?" Fluttershy trembled ever so slightly from shock, terror, and confusion. Her bunny friend simply rolled his eyes before squeaking and pointing at the letter again.

"You think I should go...? W-why?" Fluttershy asked, her cyan eyes growing wide from shock. As Angel began to explain his reasoning, Fluttershy continued to stay huddled by the door and shake.

"S-so... You think that maybe this mystery pony and I could get along really well?" Fluttershy glanced over at Angel, who hopped over to her and began to pat her head. He began to speak again, and Fluttershy's ears caught every squeak.

"Oh? Y-You think maybe I should try some more things? I don't know, Angel..."

The rabbit gave her a worried glance, before he spoke again.

"Y-You're worried about me not getting enough social interaction? Maybe you could be right... Oh, but I'm not sure! What if this pony is too loud or too scary?" Fluttershy continued to stare at Angel and question him, to which he responded the best he could. Sure, Angel could be a real brat sometimes, but he genuinely cared for the yellow Pegasus.

A while passed before Fluttershy stopped asking questions. She quietly stood up and sucked in a huge amount of air, before exhaling loudly. She closed her eyes for a moment, before glancing at Angel and nodding. "I... I guess it won't hurt to try."