The Gumdrop Files

by MintCakeWrites

Rating: everyone
Tags: Anthology, Original Character, My Little Pony: Friendship is Magic, Spike, Comedy, Cutie Mark Crusaders, Pinkie Pie, Slice of Life
Length: 9178

The adventures of Gumdrop, Ponyville's premier PI. When he isn't at school.

In a town full of missing imaginary friends, disappearing blankies and things that go boing in the night, there’s one colt you can count on. Who can the students of Ponyville turn to when no adult is available? Who will stand against injustice for the low cost of a hoofful of candy? Who shouldn't have read those old Detective Comics in dad's study?

Follow the adventures of Gumdrop and his "Detection Agency", as they battle the nefarious forces of Treacle. Be amazed at the daring deeds all across Ponyville, from the shady booths of Sugarcube Corner to the dizzying heights of the swings.

Dolls found, diaries recovered, days saved.
Agreeable fees.
Bedtime at 6.

A collection of short stories about Gumdrop, an earth pony colt who's read one too many of his dad's comics. Styling himself as a hardbitten gumshoe, he takes on cases for ponies all over Ponyville, from the mildly serious to the utterly bizzare. So long as there's a cookie at the end of it, Gum's on the case.

Cover art by Mr Tech aka hugo231929 on dA

Published 2017-12-20 15:10:11 UTC
Last updated 2018-02-12 15:15:38 UTC

Card Sharks

It was a good week for trouble. Dark days, storms brewed on the horizon. Local pegasi were real riled up over a cider shortage. Made sure everypony else suffered for it. Left folks in a real bad mood. Most would keep it to themselves. Other ponies preferred to lash out. Arguments over spilled milk.

Heard rumours on the streets. Whispers of something big happening. It’s a sad world when I know that’s good for business. When folk are whispering, it means trouble. Trouble means somepony is willing to pay to get out of it. Wasn’t too long before I had a knock on my door.

It had been some time since my last case. Real messy work. Took a week to get the sap out of my tail, but it was worth it. The pay fixed my empty sweet cupboard, now full of goodies. Winter was approaching, snack times were wearing thin. A colt would be lucky to get an extra turn on the slide for just a cookie, ponies had to start saving up. Figured the job would be a simple one.

I called for my late-night visitor to come in. Enter a young filly. Coat like bubblegum and hair of raspberry ripple ice-cream. Just had her birthday. Good food, good time. Wasn’t invited. I’m used to it. Most don’t want me around unless I’m needed.

And I may have lost the invitation. Bookbags are portals to other worlds. Check the documents, I wrote the essays myself.

“I hear you’re the kind of pony that helps,” she moved closer, horn’s glow removing her hat. Had that ‘I know what I want’ look about her. I know a good few colts who’d get into a pie fight over somepony like her.

“Depends on the help.”

She slid a picture, “I need to find this. It was taken from me.”

I gave it a look over. Standard affair. New craze had swept the lower levels of the playground. Big players had their footballs to play with, the brainiacs had found a card game. Came from a distant land, creatures battling one another. Took a smart pony to crunch the numbers, smarter one to understand the rules.

I’d seen the way ponies were acting over just opening new packs. Like a foal chasing a new sugar high. Makes me quake thinking about what it was doing to their minds. I stayed away from that side of things. Just another thing for ponies to spend their hard-earned pocket-bits on.

This colt doesn’t need another vice.

My dad already has one in the workshop.

Picture was of a card. Could see why somepony would want this, all shiny and cool looking. Knew a few colts who’d want their hooves all over it. Remember thinking how’d a sweet thing like this end up with one of these?

“Doesn’t look like the sort of thing a filly like you should have. Coltfriend lost it?”

“I don’t have one. It’s mine,” cold reply. She was hurting. Sentimental value, not about the bits.

I offered a seat, and pulled open a new carton. She declined a glass, so I helped myself. Should stop drinking juice that late, but that’s not important.

“Where did you last see it?”

“I was at the school park. Some colt came up and asked if he could have a look at my collection. I let him and when my head was turned, he was gone.”

“Along with the card. This is going to be tough, market’s perfect for something like this,” I sipped at the amber. Nothing like an ice-cold apple taste to wake the mind.

A pink hoof smacked into the desk, “I don’t care if a dragon has it! I need it back.”

I nodded. She meant business, and I couldn’t say no to a filly like this. Also, that desk couldn’t take a lot of punishment

“Like I said, tough. Not impossible. Standard fee, half up front.”

The unicorn hesitated, like she didn’t expect me to take the case so readily. She placed the payment on the desk. I gave it a sniff. Raisin. Nice.

“I’ll get in touch when I know more. Expect results by the weekend. What should I call you?” A name is always good, but some prefer to stay anonymous. I never questioned, so long as the pay was fresh.

The hat had found its way back on her head, “Whip, Strawberry Whip.”

Like that, she was gone. I took a moment, finishing the glass. I glanced to the carton, could easily go for another. Later.

Case first. There were plenty of ponies who could know where something like this could have gone. I should start by hitting the normal sources. Spike was a potential fence, and he owed a favour after the missing gem case a few weeks back. Sugarcube was a good spot for a stakeout, plus Pinkie might have seen something. Sweet treats make warm seats, and who doesn’t want to gossip a little.

I looked at the pony in the mirror. Set that up to make sure the hat fit OK a few weeks back. Hadn’t quite hit the hard-bitten detective look I was aiming for yet. Lacked the 5 o’clock shadow. Stood outside at 5 everyday trying to catch that shadow, still nothing. Just a fine orange coat and a yellow mane, like one of those adult mixed drinks. Had a taste of one once. Tasted nothing like punch.

Phone started to ring. String making that wonderful clatter. I brought the can up to an ear. When the can rang, it was rarely good news. It wasn’t.

The case would have to wait. Something far bigger came up that night. Should have guessed, nothing good happens on a Thursday.

Bath time.

The day was grey outside. Cleared up when Ditzy moved out the way, but the cloud remained. Despite the easier light, I was still grumpy from the events of that morning so far.

A grilling from the land-pony before I went out. Could see where she was coming from, but getting that ball back involved tussling with the Apple’s pigs. Can’t blame me for getting the kitchen muddy when I got back. Something else about toys being left out. Tried explaining it was vital evidence from another case, but that didn’t slide.

Then came the punishment. Milk. Unless it’s chocolate flavoured, it can go back to the cows.

Hat on, notepad ready. Investigation time. First stop, Sugarcube Corner. Pinkie Pie knows everypony in town. Rumour had it she kept a file on their party likes and dislikes. First step to a party is preparation. If something was going down, she’d be the one to know.

The smell of cinnamon was heavy in the air, chased by fresh baked goods. I took a rough look around. Quiet for a day like today. Guess the weather was keeping folks inside. Smart. Raincoats are silly, and my umbrella went missing weeks ago.

The town’s favourite pink pony had finished serving when she caught my eye. Silent nod. Serious mode engaged. She placed her guard gator on the counter and took me to one side. Smart mare, knew how to interrogate. Learned that skill from her last summer. All about lamp positioning, simple.

“I’m looking for something, might have passed through here,” I flashed the picture.

Pinkie nodded, “Worth a lot.”

“More than you know.”

“Who’s the poor pony who’s been preyed upon?”

“Young filly, Strawberry Whip.”

“Sister to Liquorice Whip,” a dossier on the older Whip thumped on the table. Stallion, candy yellow coat. Set of weird shaped dice as a cutie mark.

“What have you got?”

“Likes games of all kinds, especially card games. Three time Sorcery: The Get-Together Ponyville champion. He’d be interested in the big game today, too.”

“Big game?”

“Monster Mash. Playing for marbles at the big tables.”

“Big tables?”

Pinkie nodded, “All ages welcome.”

“How do the kids get up there?”

“Stools.”

“Makes sense.”

“There’s no money involved, just marbles.”

“Got it, makes no sense.”

Pinkie offered a cookie. Can’t say no to the candy queen. It was sweet: chocolate and hazelnut. I wrote a few notes in my pad. As well as a kick-flank drawing of me fighting ninjas. Pinkie approved.

“You need more belts. If you want in on the game, you’ll need a good deck,” Pinkie gestured to her own prize deck, “Buy-in is your best three marbles, winner takes all.”

I frowned, “That’s a big risk. Surely they’re not playing for keeps.”

Pinkie nodded. Pieces started falling, this was trouble.

“You can’t be serious!”

“I’m not, I’m Pinkie Pie, but this is a super-duper big deal,” she grabbed my cheeks, “SUPER-DUPER! You better be careful, Gum!”

“Pinkie!” a voice called her away and back to work, leaving me some time to think it over. The case had jumped considerably. Went from a simple recovery to a high stakes game. Best bet was to investigate this tournament and see what my options were.

I left Sugarcube Corner, after snacks of course. Next person to interview, one resident known across Equestria. You might ask yourself how somepony like me ends up knowing him. I’ll let you wonder about that.

Spike is a good guy, helped me out on a few cases and I’ve kept his O&O habits under wraps. A reputation could take a nasty knock with information like that. It’s not a pleasant thing to do, keeping secrets hidden. It’s gotten me in trouble a few times, but sometimes you got to have a leg up on things.

I explained the basics of the case, he agreed to help however he could. Turned out, he had a Monster Mash deck on him at all times. He talked me through the basics of the game, gushed about his carefully customised dragon deck.

“So you take these cards, then turn these to activate your power crystals. Next, you can play this card from your hoof which triggers this effect. Still with me?”

I stared at the sheer number of cards on the table.

“I think this whole thing might go better with you playing,” Spike’s a good guy, but this kind of thing wasn’t my slice of cake. Most complicated game I had played was Go Fish.

“Come on! You’ve got it. You just need to make sure you get Ultra Metallic Dragon Queen out and BAM! You’ve won!” Not sure where this confidence was coming from, maybe it was a play. Still had a small suspicion that the dragon was in on the whole play.

“This is really hard for a kid’s game. How do you know this so well?”

“Oh, um, you know… played with kids. Only because they asked me to, you know. Because it’s a kid’s game really, I just like the pictures,” Nervous look, eyes darted side to side.

“Spike, do older ponies play this at all?”

“OK, I gotta go do the thing. In the place. Good luck Gumdrop!”

“Wait is there anything… else… I need to know,” By the time I finished the question, he was halfway down the street. Ran like the reaper pony himself was after him. I just added it to Spike’s file.

I took out the photo again, comparing it to the other cards. Made sense that somepony stole the card to use in the tournament. Somepony who needed it to win, and bad. Question was, who had taken it. I figured the best way to find out was to play every pony until I saw it, then raise the stakes in the game. Big risk with Spike’s cards, but the client comes first.

I made myself scarce, had to collect my marbles. I had a tournament to win. I managed to get back to the office, only to find the client was waiting for me inside. Offered her another juice, but I ended up drinking it myself.

“How’s the investigation going?” Strawberry asked. She looked worried, stressed. Like a mother when you’re in new clothes.

“It’s going places. Reckon your card has been taken for the tournament today.”

Strawberry swallowed, now she was nervous, “O-oh. What’s your plan?”

I rattled around for my secret stash, finding the jar and offering one to the pink filly. She declined, smarter pony than me. These things will kill me one day, but it’s a big job. I took off the wrapper and popped it in, white stick poking out. Cherry flavour.

“Need to find out who’s taken your card. Gonna enter the tournament myself. Reckon he took it to use it.”

“What?!” hooves, again, crashed on my desk, “You can’t! you don’t know the first thing about the game!”

I winced at the marks on the furniture, “Spike taught me the basics and I-“

“What’s the best crystal to creature ratio? Best way to counter a three tier Bass Cannon set up? How many creatures can you inverse summon on your third main phase?!”

“… inverse what?”

Strawberry groaned, throwing her hooves up, “I’m never going to get it back!”

My chair made a satisfying crash as it hit the ground. Strawberry saw through the accidental noise, so I paused for dramatic effect, “Get a hold of yourself mare! I might not know how to play, but together we can win this thing!”

I imagined I looked especially heroic there, and let the moment hold. Strawberry eventually pulled me back to the room.

“I guess… but I don’t know anything about this tournament!” She looked to me.

I searched behind my desk, pulling out the Jar. I told her what I knew so far as I dug out my best three marbles. A professional needs to keep a promise.

“You paid for a job, I’m gonna see it through to the end. You came to me for a card, I’m getting you that card.”

The can rang. I glanced to Strawberry before answering it. A short conversation.

“First, have you had lunch? Mum's made hayburgers.”

We arrived at the tournament just in time for registration. The set up seemed easy enough. Ten matches, scoring points for wins and draws. Whoever scored the most, takes the marbles. Colts in charge of the tournament didn’t care that we entered as a pair. So long as we had the marbles to cover it, and only used the one deck, it was ideal for them. It wasn’t easy letting so many marbles go, but I had faith in Strawberry Whip and Spike’s eye for good cards.

We scanned the crowd to check out the competition. They seemed to be the normal cluster of ponies to enjoy this sort of thing until Strawberry pulled at my leg.

“There! That colt!” she pointed at somepony I knew well enough. We strode up to him as he lazily flicked through his cards, wearing a small smirk.

“Well well, gumshoe Gumdrop. What a surprise to see you here,” a deep purple coat with a matching black cape. Add a permanent sneer and a set of diabolical wings, you’ve got yourself one slice of bad pie.

My arch nemesis, “Treacle, what are you doing here?”

“Him!” Strawberry pointed at the pegasus, “He asked to look through my deck! When I checked later, the card was gone!”

Treacle had a face of pure innocence, pulling at his perfectly styled mane, “Me? Why, I would never steal another pony’s special card.”

I snorted, “Not likely, I remember the time with the pies!”

“They were a special gift.”

“The apple crates!”

“The Apple family said they were going bad, I needed to dispose of them. Hardly my fault if there was a picnic happening.”

“The bees!!”

Treacle paused at that one, “With the bees I will admit some hoof in the matter, but come now. We’ve discussed this with Miss Cheerilee. I’ve done nothing wrong.”

Strawberry glowered, “Gum, if anypony has it, it’s him. It’s got to be!”

“Alright, Treacle! I have a wager!”

The spawn of clouds and sprouts raised an eyebrow, “Go on.”

“We challenge you to a match in the tournament! If we win, you give back Strawberry her card!” I stomped for dramatic effect. A few colts who had formed an audience gave a little applause and a few woops.

“Very well!” Treacle stood dramatically on his hind hooves, one on the table. “And if I win, then you must…”

The dramatic pause hung for moment too long. Treacle looked around nervously.

“Er, anypony have any ideas?”

“He could give you all his snacks next month?” an unhelpful voice suggested.

“Aha! Yes! If you lose, I get all of your snacks!” Treacle cackled as perfectly time thunder rolled.

“You fiend! As much as those cookies mean, the job comes first! You’re on!” I stuck my hoof out at him, as if it were a fully loaded slingshot.

A bell rang. S bored teenaged unicorn stood up, announcing the beginning of the tournament. The match against Treacle would have to wait. Strawberry and I took our seats, shuffling Spike’s deck.

The first three matches were simple enough. After the second, I had a better understanding of the rules and the terms. Still felt out of place sat in such a large gathering of eggheads, but Strawberry didn’t seem to mind. Almost like she was in her element, surrounded like a lighthouse of hope in a sea of nerd.

Felt weird that we were playing against colts that were far too old to be playing a foal’s card game, but I put that to one side. It didn’t help that half of them were supplying the wooshing and magic noises in their attacks.

Land-pony once said that some ponies don’t grow up, just older. She said it wasn’t a bad thing, but I got the feeling it was directed at somepony in particular. It isn’t dad’s fault he still makes model airplanes. Planes are cool, especially when you run around making the shooting noises.

Fourth match it was getting tricky. Stallion by the name of Pencil Pusher was our opponent, used what Strawberry called a ‘mill’ deck. Didn’t see anything to do with flour, so I figured it was a gaming phrase. We took him down with a lucky draw and a good deal of imagination.

I imagined a dragon eating his griffons.

We lost out on our fifth match, but I had noticed a few odd things. A lot of these older ponies had cards that were as shiny and cool as Strawberry’s missing one. By the sixth, I figured it was time to do a little more digging.

“There’s one thing I don’t understand,” I began over a break of vegetable crisps, “Some of these ponies have bought their cards. Why don’t you just buy a new one?”

Strawberry shot a sad look, backstory time.

“It isn’t really my card, it was a gift. I was young, in love. He taught me how to play, taught me about things that no colt had ever taught me before. Risk, Discord’s Chess, Ponyfinder, a whole new world! Now he’s gone!” She sat, trembling a little.

I paused for a moment, “Sorry for your loss.”

“He said he’d come back after summer camp, and gave me the card to look after! I can’t lose it!” Her eyes brimmed with tears. I’m no good with this sort of thing, so I followed my tried and trusted technique. A cookie, a smile, and a line pulled from a movie.

“Don’t worry, Gum’s on it sweet cheeks. I’m gonna make this right, but I can’t do it alone. You in?” Finished off the line with a badass pose, despite the grumbling from the others at the table.

“You’re taking this a little too seriously, dude,” one colt mumbled into his snacks.

I didn’t care, there was a filly who needed cheering up. It paid off, Strawberry wiped at her eyes and smiled.

“Alright, let’s do this!” she joined me, standing on the table. “Wait, did you just call me sweet cheeks?”

Next games were close. We took one loss and a draw, but came out decently on the other side. We were just one more match from taking on Treacle. Rumour had spread though, our dynamic duo taking the tournament by storm. A new comer with a deck like no other, and a filly with more skill this side of Neighpon.

Then came our moment. We took our place opposite Treacle, who sent a smarmy smile our way. The referee looked down at both sides.

“Alright, this is the last match. Ready?”

I glanced to Strawberry and returned the nod, “Ready.”

“Ready,” Treacle yawned, mockingly waving a hoof near his face.

“BEGIN!”

First few turns were nothing special, set up and a few probes on our defences. The real challenge came on Treacle’s fifth turn, as Strawberry leapt to her hooves.

“That’s the third wonderbolt you’ve played! This is an anti-dragon deck!”

Treacle oozed a smirk, “Well done. Dragon fighters versus dragons, let’s see how grandmaster Spike’s deck matches up against its toughest foe yet!”

The smile turned to near maniacal laughter at my reaction, “Oh yes, Gumshoe! I know that it isn’t your deck! And I will humiliate you, your filly and that two-bit dragon for even pretending to play this game!”

His attack was unstoppable, turn after turn of pegasi came at our dragons. I could see the war in my mind, the battlefield streaked with groaning dragons as the crack team took them head on. Treacle himself flying among them besides Captain Spitfire.

Soon, we were down to our last crystal before game over. Strawberry grabbed at her as she racked her head for a counter to these attacks. The look in her eyes told me all I needed to know.

I placed a hoof on the deck, “One more turn. We can do this.”

A nod.

I added the card to our hoof.

Treacle’s grin faltered at my growing smile.

“We play The Fair Princess, which activates our commander’s second effect: Coronation!” I stood beside our newly crowned Dragon Queen.

“And that’s not all!” Strawberry cried, “We then use our spell tome: Deus Ex Machine! This makes our Dragon Queen take on her final form.”

The battlefield quaked as we rose in the air, Treacle’s jaw dropping. I gave Strawberry a final nod before we shouted in unison.

“COME FORTH, ULTRA METALLIC DRAGON QUEEN! TAKE HIS POWER CRYSTALS!”

The sound roaring of our dragon was unlike anything I had heard before. The scream sent pegasi and clouds soaring away, leaving on Treacle standing alone. He let out a cry of help before he was eaten in one gulp.

“We did it!” Strawberry cried, leaping as high as she could. I flashed a smile, revelling in the victory.

Then another player asked us to keep it down and to get off Treacle. I spat out his cloak, letting him get to his hooves with a flap. Treacle gave me an evil glare before fleeing the scene, deck left scattered on the floor.

“Ah jeez, hey little dude! Come back!” the organiser gathered the cards in his magic, “Aww, if he tells his mom about this the game will end up banned. Alright ponies, pack it up. Come get your marbles, we better go.”

A bittersweet victory.

The next day, I finished off writing my notes on the case. Got the idea from the Pinkie. She told me about her friends keeping a diary or writing letters about their adventures. Seemed like a smart move, gave me something to do on the quiet days.

The door squeaked open, and a familiar filly trotted in. She dug around inside her bag for a moment, before taking out a cookie. Strawberry sighed as she passed the remainder of the payment. This one was chocolate chip. Her ears flicked as I passed it back.

“Didn’t find your card, can’t take payment for a job not done.”

Strawberry pushed it fowards, “B-b-but you helped me get something more! Look!”

She turned to one side, showing off the fresh cutie mark. Deck of cards mid-shuffle, perfect for her.

“I got it when we won. Card or no card, I have to repay you for this!”

I tapped a hoof against my chin, before ducking under the desk. I took out the special lollipops, the ones for celebrations. Peppermint swirl, perfect. I passed one over to Strawberry, helping her unwrap it.

“It’s strong for a first timer,” I smiled a little as she winced at the flavour. “I’m a professional, Miss Whip. I didn’t get you the card, I don’t take the payment.”

I waitied for the disheartened look on her face, “But I’m looking to expand. Last few cases were tricky ones, and I'd like somepony to watch my back. It’s hard work, but I could use a partner. What do you say?”

My desk made a womph when it finally collapsed, this time from a filly jumping over it. I returned the hug awkwardly, hoping that the sweets inside had survived.

“Thank you, Gum! I’ll help in anyway I can! I feel like we can take on the whole world, right every wrong! Justice to Equestria!”

“… we’re still in school.”

“Yes, well, still. Thank you,” she stood up a little straighter, fixed her hat and nodded. “See you around, Gumshoe.”

And with that, she walked out my office. As I watched her walk away, I couldn’t help but smile. Sure, I didn’t get the case. Treacle was still loose, and I now had to explain to Spike why his cards were now slightly muddy. I stared at my poor desk, then let out a sigh. It came with a smile. For all that went wrong, I now had a partner. More than that, a friend.

I cracked open a new carton, Sweet Apple Acres 100% fresh. The cool liquid hit the tumbler with a plop-clink. I took a moment to savour the smell of those sweet apples before tilting the glass.

The can rang. I gave it a glare after setting the tumbler to one side. The can arrived at my ear as I worked on the desk.

“Hello?”

“Gumdrop, Spike just came over. He left something for you.” The Landpony.

I half listened as I tried to rescue the cookies from certain crumby doom, “Uh-huh.”

“He said that Cheerilee gave him a card from some game. She found it in the cloakroom last Wednesday. He asked me to give it to you, so you can get it to your filly friend. Any idea what it is?”

I stopped, and let a smile appear. Sometimes fate works in weird ways. Sometimes, it all works out fine.

“Also, what’s this I hear about you getting in another fight with Treacle? And why is the kitchen caked in mud again? We’re going to have serious talkings when you get out of that den, mister!”

I did say sometimes.

Filly Fooling

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