//------------------------------//
// Filly Fooling 
// Story: The Gumdrop Files 
// by MintCakeWrites 
//------------------------------//

Da-dadada-da-dada. Da-dadada-da-dada. 

I sighed, tapping out the beat again and again on the desk.

Da-dadada-da-dada. Da-dadada-da-dada. 

I looked over the office for an easy distraction. I had exhausted all the cleaning I could do, even managed to clean off the rust from the filing cabinets. And organised the case files. And categorised the emergency stock.

Another sigh. Back to the black paper in front of me.

Da-dadada-da-dada. Da-dadada-da-dada. 

THUMP

“And what’s on your mind today, boss?” a lump of bubblegum called from the hammock, nose buried in a comic.

Strawberry Whip gave my mane a telekinetic poke as I groaned into the desk. The last one hadn’t survived our first meeting, but the replacement was holding stronger than I thought it would. Reinforced wood was a good call in this line of work.

“Don’t know who to write this Hearts and Hoofs Day card to,” my head thumped against the desk with my grumbling. With any luck, beating my head would force some sort of words to come out. Strawberry continued to flick through her comic.

“Well, I always write one to my mum. Why not do that?”

“Because I do that every year. The Land-pony’s got loads of them, all tucked away.” THUMP

“Why not somepony in class?” Strawberry looked over, shying back under the comic at the glare. “Ok then… what about Miss Cheerilee? I’m sure she’d appreciate it.”

My face scrunched up in a frown and lifted away from the desk. “Sure… but everyone in class gives her one anyway. If I have to do it, I want it to be special!”

“Why do you have to do one anyway? If you don’t have somepony to give it to, why bother? And why does it have to be special?”

“Because,” I groaned as Strawberry gestured for me to continue. “Because Dad asked me to. He said it’s something I haven’t tried before and that I should try new things every day. I can’t disappoint him.”

“Then why don’t you write him one?”

“I don’t think that’s what he-”

Da-dadada-da-dada.

We both looked to the desk. My hooves hadn’t started acting on their own. Our eyes moved towards the door as the knocking repeated. With a practised twirl, Strawberry flicked herself off the hammock, floating a hat to her head. I pulled mine on and swept the card under the desk before nodding.

Business time.

The door creaked open, hinges begging for oil. Strawberry trotted over to my side, standing next to my seat as I tapped my forehooves. In came trouble. Three fillies, well known across Ponyville for their exploits. Well-connected too. Made me wonder why they decided to call in on my business rather than go to their sisters.

The Cutie Mark Crusaders: a storm in a teacup. Now my office was the pot. Whatever problem they had, it was going to be big.

“Uh, hey there Gumdrop, Strawberry,” Sweetie Belle, perfect name for a unicorn like her. Sweeter than all the candy in my drawers and a voice that could out-ring anypony else’s. She was my go to when the situation needed a musical number.

That happens more than you think.

“Ms Belle, Ms Bloom, Ms…Scoot? Ms Loo?” I received a confused nod. “Please, take a seat. What can we do for you?”

Strawberry summoned three stools for the group, though space inside the office was lacking. The Crusaders managed to pile on top of one another awkwardly. I examined the clients carefully, trying to piece together what had blown my way.

“We heard you could help us with something.” The fastest land-based pegasus I know: Scootaloo. Also the reason behind most of Ponyville’s traffic laws. Her scooter was legendary around the skate park, surviving ordeals that should have destroyed it long ago.

A quick nod as the glasses came out. For such high-class clients, only the best should be served. Shame that one of the ponies present made the stuff. I took a sip from my drink, gesturing for the fillies to carry on.

“Y’see, normally this somethin’ that me an’ the girls can handle, but this time that we could do with some help,” Apple Bloom explained. Didn’t even see the liquid disappear she drank it so fast. Scary girl.

“Pip had a Hearts and Hoofs Day card all written out, ready to go. Then, all of a sudden, BAM!” Scootaloo’s forelegs slammed on my desk, my own flying out on reflex to save it. “It’s gone! Same with Featherweight and Twist. Now loads of ponies are saying that their cards are missing too!”

“So it’s a repeat crime? Any suspects? What’s their MO?” Strawberry filled in for me as I began to write down notes. She was a good partner, fantastic eye for things I’d over look or never consider at all. That and she could write cursive. Unicorns and their fancy writing.

Sweetie Belle had set her drink to one side, “We don’t want to point hooves at anyone yet, we need to catch somepony in the act.”

“We’re gonna work on our card for Miss Cheerilee, try an’ lure whoever’s stealin’ these cards with that,” Apple Bloom added, eyeing up Sweetie’s glass.

“So you need us to keep an eye out in case they get away?” The trio nodded at Strawberry’s question. She caught my eye, motioning for me to talk.

I finished my notes, mostly intricate drawings of how my new castle would look. Twenty foot deathslide is a must have. My hoof idly tapped the desk while I mulled the request over. “Alright, we’ll take it on. Take it you know the fee?”

The Crusaders nodded, throwing the payment on the desk. Strawberry gave it a look over, nodding her approval, “Raspberry and white chocolate. Good choice.”

“Where do we meet you?” I gestured for the girls to stand, taking the lead.

“At the old gazebo near Sweet Apple Acres. The one where… well, I’m sure you remember that incident,” Scootaloo gave a sheepish grin, mirroring her two companions.

I don’t think anypony could forget that incident. The whole town had been beaten to a fine paste after Big Mac’s love fuelled attack. I even ended up inside the pitfall before it had been filled in. Learned a fine lesson about watching where I’m going after that.

“Right. Good doing business with you girls, see you soon.”

Strawberry collected the empty glasses as the Crusaders took their leave. With a smile and a slam, they were gone. I stretched and moved back to the desk for a peppermint swirl. A soft pink glow surrounded the jar, moving it out of my reach. Eyes flicked to Strawberry who shook the jar and took one for herself.

“Why would somepony steal cards? What good does it do?” she pondered around the sweet, sending the jar back to me.

“It’s about looking good. Three explanations,” I needed that sugar high. “First, if there are no cards given out, it makes theirs even more special.”

The lid came off with a pop of pressure and the scent of mint wafted lazily into the air. “Second, if they steal all the cards, they can choose the best one. The others get returned mysteriously.”

The candy popped into my mouth, clicking against teeth. “Third, they want to know who each card is for.”

“Blackmail?”

I nodded, sucking on the sweet slowly. Strawberry paced a little, frowning.

“If it’s the last one, the plan isn’t going to work. Everypony knows about the Crusader’s card to Cheerilee,” She tapped her chin, looking around the room. I recognised the glint of an idea.

“We can go through with the plan anyway, but we need something as a backup.” She moved over to the desk, horn floating the mess off the floor.

The sweet hit the other side of the room as she picked out the bait.

“I’ll get you some crayons.”





The air still had an early Spring chill. Birdsong filled the air, reminding the citizens of Ponyville with the season came new baby animals. Even more mouths to consider for the ponies who looked after the poor things. I shivered, as I remembered the last Winter Wrap Up. Not all the hot cocoa in the world could warm me up after a quick dip in the lake.

“You know, I get the feeling this has been done before. Sitting and watching this gazebo,” Strawberry grumbled in the bush next to me. We had been sat inside it, watching the Crusaders work on a card slightly bigger than a house. Currently, the trio were readying what looked like catapults loaded with glue and glitter.

“What makes you think that?”

“Because the ground has been swept so we can sit here comfortably, the branches have been trimmed so we can look out only at that gazebo, and several ponies have waved,” on cue, Strawberry returned a silent hello to a passing Ditsy.

I snorted and brought up the binoculars, anything to distract myself from having to write that card. Everything in Ponyville looked normal. Friendship Castle loomed in the near distance, towering over every other building in sight. Sweetie Belle’s older sister was entertaining guests at a café, our premier weather team was on cloud dismantling duty, something was exploding near that performing mare’s cart.

Perfectly normal day. Red flag.

“HI GUM!”

I found out what the inside of a cloud feels like: wet.

Strawberry managed to catch me as I came crashing down, Pinkie bouncing on the spot by the bush. “What’cha doing? Are you spying on Apple Bloom?”

I wrinkled my nose, “It isn’t spying.”

“But you are watching!”

“… could be?”

“Oh cool! Are you waiting to give her a card? Oh oh, or maybe you’re waiting to see if somepony else is going to! Or maaaaybe you’re thinking about Sweetie Belle or Scootaloo! Ah! Tellmetellmetellmetellme!” She danced on the spot, stopping as Strawberry’s hoof came up.

Strawberry tapped her own nose, winking, “Client confidentiality.”

She blinked at my stare, “What? It was my mum’s word of the day.”

Pinkie bounced even higher at that, landing and taking out her own sleuthing hat. Chequered deer stalker, classic. She landed in the bush with us, peering down at the oblivious fillies.

“So, what’s the job?”

“Card thief,” Strawberry replied, eyes narrowing.

“Didn’t you deal with this before?” Pinkie frowned, her tongue coming out at the difficulty of the thought.

“No?” I joined in her confusion. “Oh, no. We’re talking about these kinds of cards.”

I held up my still blank card, ears dropping as I realised my mistake. Before I could blink, Pinkie had taken it off me and began studying the card. I felt the heat rise to my cheeks as embarrassment set in, hooves failing to get the card back.

“This is really good Gum! I mean, it could do with some work. And colour. And anything really, it’s just in the shape of heart right now,” Pinkie held up the blank card. “But it’s a good heart!”

“It’saworkinprogress,” I continued to grab at the card, glaring at Strawberry as her magic moved it out of reach.

“There isn’t even a name on in yet!” Pinkie spread her hooves out, gesturing to the card then me. “Haven’t you got a special somepony yet?”

“Working on that, give it back Strawberry!”

My nose scrunched as Pinkie held me in place, her face worryingly stern. Carefully setting me down, her hindlegs came together in a position I thought impossible for ponies. Shows me what good stretching can achieve. Pinkie brought her hooves down, her face dropping to a perfect calm.

It took me a moment to notice that Strawberry had done the same.

“Finding a special somepony on Hearts and Hooves Day is super important, Gum. Even if it’s just to your mom or your teacher or a friend, it makes a pony’s day to get a card,” Pinkie explained, never once opening her eyes. Behind her, I could hear my partner quietly say “om” over and over.

“But I don’t have a special somepony! And I always give one to the land-pony, Cheerilee is getting that masterpiece,” I pointed to the Crusaders’ glorious work, which had become more glitter and ribbon than card by now.

“Then why not a friend?” Pinkie opened one eye.

I scuffed a hoof, “… all the colts would laugh if I gave them one.”

“Then why not give it to not a colt?” Her hoof pointed at Strawberry, who continued to ‘om’ in blissful ignorance. The noise stopped as the gears in her head caught up with the conversation.

“Wait, what?”

“I mean, you’re together all the time! You two are best friends! You can totally be best special somepony friends too!” Pinkie squeed at the idea, completely ruining the peaceful guru image she was channelling. She passed the card back to me, along with a crayon from her mane.

“Just write her name down, and if you think of somepony else then you can change it later!”

I looked to crayon, then to the card, then back to the crayon. “If you’re sure.”

With my reluctance fading, I wrote a simple message on the card. There was enough space at the bottom to change the name if needed, but at least it had something on it. Pinkie took it back, ignoring our faces, now glowing red with embarrassment. I was fairly sure you could fry an egg on my cheeks or put a marshmallow on Strawberry’s horn to toast. Wonder if anypony’s done that before…

“Though I don’t know what to say,
You are very important to me,
I can’t put it any other way,
Please be my special somepony,”

Pinkie read out loud, grabbing me in a hug. “Awwww, that’s so sweet! Ok! Now we’ve done that, I’m going to get some art supplies. You stay right there and I’ll be back before you know it.”

With a big spring and a trilling song, Pinkie bounced off and out of sight. We sat in awkward silence, the sounds of the Crusaders arguing over what colour paint should be next continuing in the background. I decided to busy myself with drawing doodles in the dirt.

“I-it’s just practice,” Strawberry started, slapping her hooves to her mouth. “I mean, it doesn’t mean anything.”

“Y-yeah, just a test. Right,” I tapped my own together, feeling very self-conscious at how easy the words came to me. “Say, uh you ever wondered why they call it a deer stalker?”

Strawberry’s ears flicked as she gave me a slow blink.

“I mean, who stalks deer? Heh….”

We returned to watching the Crusaders activities, not paying any attention to their antics. Despite the trio earning their cutie marks a while ago now, their talent in causing destruction had not stopped. We watched the wind up, and inevitable crash that followed as a dozen tins of paint sailed into the distance. I only hope that Ponyville was looking forward to the sudden redecoration.

Pinkie returned, still bouncing like she never stopped, carrying an impressive collection of different colouring implements. She gave a small squeak as she proudly displayed the tools at our disposal. Strawberry and I began to pour over them, trying to decide whether to use watercolour or yet more crayon. Strangely, she had also brought macaroni in all the colours of the rainbow.

“Here you go!”

“This is perfect Pinkie! Gum will make the best card with this!” Strawberry’s enthusiasm outshone my own, as I tried to bury the feeling of embarrassment in the colours. “Where did you put his card?”

“What do you mean? I left it with you,” Pinkie’s voice became strained, and I felt a cold chill over me. Oh dear.

“Nooo, you took it with you… right?” Strawberry let panic in her voice as well. Oh dear, oh dear.

Pinkie let out a nervous laugh, only to break out in frantic searching. I stayed buried in the art equipment, pretending to find the fifty varieties of beige more interesting. They weren’t. Did made me question how there were so many, and why Pinkie had them, but that came to a crash when the panic overtook all of us.

“WHERE IS IT?!” we cried, hunting around. We turfed rocks, the bush, even looking under each other at points. Our search proved fruitless, only to be interrupted by a dastardly sound.

“Mwahahahahaha!”

My eyes snapped to the source of the sound, knowing full well what it meant: “Treacle!”

“Mwahahahahaha! Missing something, Gumdrop?” the pegasus leered at us from a nearby tree, cape flapping in a dramatic pose. Tucked under one leg was my card.

“Give it back now, do you know what it is?” I raced towards the tree, only for my foe to glide his way out of my reach. “Treacle!”

He dashed off into the distance, my hooves pounding after him in pursuit. Strawberry Whip soon caught up, racing alongside me as we tore through the streets of Ponyville. Our quarry was only a few steps ahead, but we couldn’t close the distance.

Treacle slid under a carrot cart, the pony pulling it shrieking as I leapt over it. Strawberry shouted an apology, only to yell another as we skidded around the mountain of apples Big Macintosh was pulling. Treacle burst through the flower mares’ stalls, sending a flurry of daisies into the air. We were one window carrying team away from a cliché. Even with our fancy hoofwork, he kept ahead, his maniacal laughter only pausing as he caught his breath.

“Get back here!” Strawberry cried, her horn fizzling with magic as she grabbed Treacle’s cloak. He gave an unhealthy sounding hurk before releasing the clothing. Unfortunately for us, he wore a spare beneath it. Tiny wings flapping, Treacle took off into the distance. His laughter, and occasional cough, fading away.

We stood panting in the street, keeling over as exhaustion won. Even though he is my sworn foe, I have to give it to him: he’s fast. I barely heard the revving of wings as the Cutie Mark Crusaders caught up, wheels screeching as they came to a stop. Sweetie Belle’s face came into view, a look of concern and mild confusion.

“You ok Gum?”

“No,” I blew out the dust in my mouth. “He got away.”

“Wha’ happened?” Apple Bloom helped me up, as Scootaloo did the same for Strawberry.

“We know who’s been taking the cards, it’s Treacle,” Strawberry snarled. “But he’s long gone now.”

“Isn’t like him though, he’d gloat for longer,” I mused, gears turning. “He’s working for somepony! The plot thickens.”

“The question is, who?” Strawberry joined me in stroking an imaginary beard. “Any ideas?”

“Well, we would say Diamond Tiara, but she’s different now,” Scootaloo began, the others nodding. “I can’t think of anypony else though, at least not in class.”

“But no grown-up would do somethin’ like this, right?” Apple Bloom frowned, looking around for confirmation. We all hesitated before nodding. “So it’s gotta be somepony from class!”

“So, what now?” Strawberry turned to me, as did the Crusaders. I took a deep breath and shifted my hat.

“Our only lead is Treacle. He has the best prize he could have, my card. We need to act like we’ve got something better,” I stood up, tapping a hoof against my chin. “We need a better card.”

“A better card? How?” Sweetie Belle looked around, as if the solution was going to burst into view. As Ponyville continued to move in motion, plan began to form in my mind.

“Treacle wanted us to know we were beaten, but he couldn’t gloat. He’s on a schedule, so we need to hype something up.”

“How do we do that? and what are we hyping up?” Scootaloo frowned, her wings buzzing with excitement.

“I need you guys to go around and ask everypony for something to put on the card, even if it’s a little thing. If there’s one thing Ponyville is good for, it’s idle gossip!”

“Right, and what do we do after that?” Sweetie Belle nodded, following Apple Bloom and Scootaloo’s example.

“You tell them that Gumdrop is making the greatest Hearts and Hooves Day card ever!”





“Y’know, I’m mighty appreciative for your help in the matter, what with the missing cards and all,” Apple Bloom grumbled, standing next to my paint splattered self. “But I can’t help feelin’ this might be wasted effort. I mean, can’t you go find him and get them back that way?”

“Treacle wouldn’t dare miss out on an opportunity to annoy me. He’ll be expecting something if I go after him, so we nail him on our terms,” I tried to pick paint off my coat. The land-pony was going to be furious, a small sacrifice for the greater good.

“An’ how do we do that?”

I replaced my hat, glad that no glitter had settled on it. “That’s your guys job. With Sweetie Belle and Scootaloo spreading the word, he’ll turn up and I’ll negotiate for the rest of the cards. I’ll give him this one in exchange.”

“Y’sure this’ll work? Really sure?” Apple Bloom frowned again, looking at the massive work and the message written on it. I was still impressed I had supressed the sheer embarrassment from writing it to get it done, but the job comes first. Social suicide later.

“It’s one thing he could hold over me for years, he’ll come. It’ll work,” I flashed a smile. “Trust me, I’m a professional.”

“If you say so,” she hesitated.

“GUM!”

We both turned to see Sweetie, Scootaloo and Strawberry rushing towards us. my partner held a letter in her magic, the parchment flapping in the breeze. The trio reached us, the letter thrusted at me. a small seal, now broken, hung on the edges. On it, a strange symbol.

“It’s supposed to be a skull or something,” Strawberry explained as I gave her a questioning look.

“Huh, must be for interpretation,” I skimmed through the letter. “To my greatest foe, the time has come to do battle. I hear that you wish to sacrifice blah blah blah... Meet me at the fountain bridge at sundown. Bring the card.”

“Guess it worked,” Apple Bloom sniffed, the other Crusaders looking up at me.

“Right, game plan,” I brought the team in for a huddle. “Strawberry, you’re with me for card delivery. Crusaders, you’re on capture duty. Wait for my signal before nabbing him.”

“Nabbing?” Scootaloo raised an eyebrow.

“Catching. We’ve only got one shot, but those cards are the priority. Got it?”

“Got it,” the fillies echoed back, our hooves coming together for a victory shout. What could go wrong now?





Sundown came around quickly. Maybe Princess Celestia wanted to get the day done with, I certainly did. Strawberry and I approached the meeting point, shaking off the feeling of dread. We were only stood a few moments when a black shape leapt from a nearby tree, gliding down to the bridge. We both stood ready, tensed and snorting as the new arrival reared up and cackled into the orange sky.

“Mwahahaha! You have come to your- wow,” Treacle paused as he took in our side of the trade. “That’s a big card.”

“Yeah.”

“… I’m not sure how I’m going to get that home.”

We stood looking at each other, slowly feeling the awkwardness build up. I coughed as Treacle ruffled his feathers, Strawberry sat on her haunches and began tapping a stone around.

“So, uh, can I use your cart?” Treacle asked. Strawberry shrugged, gesturing for him to continue. We resumed our positions.

“Ahem, mwahahahaha! You have come to your doom, Gumdrop! But, it’s a noble sacrifice all the same, I applaud you.”

“You’re a dastardly fiend Treacle, but I’m willing to do this for greater good. Now let those cards go!”

“You mean these cards?” Treacle hefted a large sack into view, one hoof resting on it. “They’re all here, safe and sound. All you need to do is bring me the card.”

I looked to Strawberry who gave me a confident nod. She moved the card handle to my mouth and moved to one side to let me pass. With a grunt of effort, I pulled the precious trade item towards the cackling maniac. The sack lurked dangerously near the edge of the bridge, too close for my liking.

“That’s close enough!” Treacle cried, the card resting on a flat surface. “You will move away, then let me take the cart. Once I have left, you can take the cards.”

I nodded, tapping my hoof twice. Go time.

Treacle cautiously moved forwards, keeping an eye on me the whole time. I adjusted my hat, watching his every move carefully. Just as he reached the cart, a strange smile appeared on his face. He spun on the spot, grabbing the cart with his tail and leaping towards the sack.

“Now Sweetie!”

A net sprang from a nearby bush, the end wrapped in Sweetie Belle’s magic. Treacle saw it approaching, his tail dropping the excess weight to jump ahead. He bit into the sack, the net snagging around his lower legs. His grip wasn’t strong enough, slipping through his teeth as he struggled. I leapt through the air, snagging the precious cargo as we teetered on the bridge. Treacle managed to wriggle out from the net, taking one look at me before darting. He had lost.

I managed to regain my balance, pulling the sack up and away from the water. It was easier than I thought, given the sheer number of cards inside. I turned around triumphant, feeling the sack flap around in the light breeze. Then a card flew past.

I then saw the gaping hole in the sack, cards floating away in the water or in the air.

“… darn it.”





The conversation with the Cutie Mark Crusaders was rather awkward afterwards. None of them blamed me for what happened, for all we knew Treacle could have rigged the sack to break at any given time. It did little to raise my spirits. Treacle didn’t win in the end, but we certainly lost. It didn’t take long for ponies to ask why I was holding a sack of cards over a bridge. Take that out of context, and I knew I’d be blamed for it.

I spent the remainder of the day hidden in the office, trying to put off coming home. The Crusader’s card still lived, and they had a plan to make it up to everypony else at school. It’ll help calm the anger of those who lost their cards. A real low moment.

We didn’t find out who Treacle was working for, nor why they were so keen on having the cards. Something told me that the final exchange was Treacle’s desire to see me humiliated, but it still felt off. Made me wonder who could be lurking behind my eternal nemesis, who could be pulling the strings.

Strawberry came by to throw a small ‘we did our best’ party, we ended up eating through most of the stockpile we had from winter. After she left to finish off some other work, I tided away the last of the wrappers. Strawberry always knew what to do when it came to cheering me up.

I was sure my name was about to be dragged through the muck at school, but with some help with the Crusaders I’d pull through. Somehow, I always did. Strawberry’s hammock was the worst of the office, covered in comics and the remains of so many treats. I couldn’t get angry at her, not for trying to help as best she could. As I organised the whole mess, I saw something fall from the pile.

A card in the exact shape and colour of my investigator’s hat. I turned it over, reading the message on the other side and smiled to myself.

To Gum
It’s easier to put this on a card
Than it is to say
I think you’re awesome and work really hard
So have a wonderful Hearts and Hooves Day
Love, Strawberry Whip