Welcome to 2022! As someone pointed out on Twitter today, a year whose name you can sing to the Inspector Gadget theme. What better omen could one have than that? Anyway, Flashfic 150 returns as always, albeit a few hours later than usual this time thanks to... well, a combination of food, family and whisky. I think that's excusable at New Year! Here we go, then. A refresher of the rules to begin with:

Here are the full rules.

You'll note that Rule 6 still explicitly disallows any G5 content. I'm still keeping that rule for now; we'll see about the future in the future. Remember, there's a rules, Q&A and suggestions thread if you want to weigh in on this or any other relevant issue.

Remember, there is no prize, as such, for this contest -- but if you win, you will be able to choose the prompt for the next contest. You'll also get a mention on the group's front page. I'll also take this opportunity to remind everyone that despite this month's prompt, you still can't break any rules that are actually Fimfiction rules. So no script format stories, no M-rated fics in this non-M group, you get the idea. Which reminds me...

...I'll hand over to Mockingbirb now for an extra bit. This is purely for fun and will not affect judging. Unless of course I decide to break the rules myself! Mwahaha etc.

The "Optional Challenge" is, write a story that also breaks at least one "rule" about how to write. Preferably, write a story that isn't made worse by breaking the rule, but instead uses its freedom to good effect.

You could break a rule that most of us learned in school, or a rule that people in fanfiction communities yell at each other, or even a tip from an accomplished professional writer. [Logan's note: Mockingbirb's forum thread may help.]

Prompt: "Break the Rules!" (selected by last month's winner, Mockingbirb)
Rating: E or T
Word limit: 150
Closing date: Friday 21st January 2022, 11:59 pm UK time (world clock)

Please reply to this post with your entry. This makes it easier for me to keep track. Please do not leave feedback until after the closing date.

Entries are now open! Have fun!

7624102
So, to be clear, the prompt won't let us break the rules of the contest itself?

7624102

We are tired of living in thy shadow, sister! But it all ends today, for obedient Luna is no more. Tonight, Nightmare Moon rises! 

I was entrusted to protect Equestria and shall do so even against you, my sister!

Pff, we have already dethroned you, thou just do not know it yet.

What evil scheme do you intend to enact, rulebreaker?

Well… We heard there is a new issue of the Adventures of Clover the Clever comic in the library.

Wait, what? You absorbed all that power of darkness in order to... read a comic?

And while we do, you shall take care of our queendom.

But I have been doing that exact thing all along.

Also, when it’s time for the night, you shall raise the moon for me, okay?

Whatever you say, rebel…

And if anypony asks for me, tell them you sent me to the moon or something.

Edit: 17 - Rulebreaker

7624102
...well, I did think of this concept last month that I would love to get out somehow.

...and there just so happens to be a rule for it! It's an old wives' tale, but...

With the spotlight on her and after many fierce rounds of sorcery, Starlight wins the title of spell bee champion.  She squeezes her trophy close to her, listening to the crowd as they rain her name.

"Star-light!"

"Star-light!"

---

"STAR-LIGHT!"

Her eyes adjust and registers a goldfish flying by her.

Starlight jerks under the light of the moon, taking in the hectic state of the castle's library.  Books are coughing up text, chairs are beating on the tables, and the rug is doing the worm.  She leans back and notices that she's hugging a waste bin.

"Bout time!" She looks down and sees a purse talking to her, opening and closing as it speaks in a familiar tone.

"...Landau bag...am I asleep?"

"Hardly, you're finally awake!  And it's me, Spike!"

The waste bin slides out of her grip, "I... I don't understand.  What in Equestria happened around here?"

"You were sleepcasting."

7624107
He already broke the rules by leaving the closing quotation marks off the prompt. That's as far as it goes.

7624102
I decided to go for a narrative twist this time. It feels a bit long winded even with it shortened to 150 words, sooo… I give you,

Pinkie Pie was a jolly mare, though a bit strange sometimes.

She lived a happy life in Ponyville, with her friends always being there for her.

Until today.

They were having a secret meeting. What were they doing, she wondered. They told her that she couldn’t come, and that made her feel sad, but she went along her day like normal, working her job at Sugarcube Corner while they met.

The next day they still weren’t back, and Pinkie worried. Pinkie worried her friends would be mad if she came to check when they had told her not to.

But she cared about her friends. She had to know.

And with a montage of cataclysm, she finally found out.

They weren’t avoiding her. They were dead.

Pinkie was happy that her friends weren’t keeping secrets from her, but she was sad she had to bury their bodies in the woods.

7624102
"1 minute patrick your telling me this isn't about flutterdash

twilight had amazing entries for her short fic contest and behold her good friend pinkie entered again, she knew far well pinkie wasn't as good as the other writers but she still enjoyed reading the stories and seeing pinkie wright so much but it always seemed to be about the same ship.

"the HMS 747" the title read.

"the HMS 747 was in a epic fanfic war, had wrote a story about how much a silly pony apple jack. she was writing a fanfic in his newest story about 2 Pegasus ponies meeting, the story said "these two ponies kiss all the time, these two ponies white a fanfic about each other all the time and they lived happily" and he told this story to the other ships, there response

"what a silly fanfic" said the other ships,
"what a silly fanfic" said twilight.
"what a silly fanfic" said Logan.

7624102

No, stop.

Luna had wanted the strength. The clarity that came with the coldness. Even the hatred, she had welcomed that to burn even hotter.

Stop.

She hadn't looked deeper. Hadn't wanted to. All she cared about was a conduit for her endless rage and loathing. She hadn't cared to look deeper, to see the nature that came with the strength she bargained for.

I don't want to be a monster.

The cruelty.

It's my life.

The evil.

Come now... Why would you want your life? It's not as though you were doing anything with it.

7624102

“Pinkie!” Twilight dashed toward the balloon-marked mare, who looked at her with a befuddled expression. “Thank goodness I found you! I’ve lost the portal to the human realm!”

“Oh, uh…”

“Pinkie?”

“Well… Cheese Sandwich came by and said he needed something he could use in a funhouse he made for a big party, and… I may have told him about the dimensional mirror thingy and let him borrow it for a day.”

“You did WHAT?”

---

Sunset looked up from her precalculus exam to the sound of consternation outside. She peered through the window and saw a mass of confused people gathered around the former Wondercolts statue, many panicking, most on all fours and one singing and dancing with an accordion. Then she watched two more stumble out of the statue base, then another three.

“Oh, horseapples…”

7624102

Twilight Sparkle Gets Stuck Within A Bad Book About A Lavender Unicorn
by: SparklingTwilight, all rights reserved!

The lavender unicorn wrote about the purple unicorn that was herself (a violaceous creature) writing about herself (a mauve mare) that was Twilight Sparkle. Sparkle didn't like this book about lavenderish furred-creatures writing about helotropish-like-colored ungulates that write about themselves. But violet-coated Twilight was stuck using Haycartes' Method, traveling within a bloviating, wordy, repetitive, confusingly verbose over-long ancient-parchment story wrapped in a Möbius strip--and that's what the studious periwinkle prancer got for trying to outwit the Muse of History in a speed-reading competition where books were selected by contestants--until the lilac-coated equine could finish writing about a persnickety plum pony writing about the perse personal protégé of the Princess who was uncomfortably reading about the writing of the research-minded purplish sentient person.

*A few days after posting, I added the phrases: "for trying to outwit the Muse of History in a speed-reading competition where books were selected by contestants", "a persnickety plum pony", and "uncomfortably" and I changed one "unicorns" to "ungulates", one "pony" to "prancer" and a "purple" to "perse".

7624102

“So, who you gonna give the ticket to, Twilight?”

Twilight froze.

“Twilight?”

The concern in Spike’s voice was distant to her as sweat formed on her brow, her composure wavering.

She could overcome this. She’d turned over a new leaf moving to Ponyville, she could be normal and accept that not everypony followed the rules. All she had to do was say nothing. Let it pass without comment. Easy.

But Spike? Her number one assistant, whom she trusted more than anypony? For him to betray her like this?

Her breathing was quick and shallow.

“Twilight, are you okay?”

No. No, she could contain it. She had friends now, ponies she didn’t want to alienate. She needed to learn to be cool about these things.

With a single deep breath, she stilled her shaking legs and smiled.

“I’m fine, Spike. What were you saying?”

“Who you gonna give it to?”

“WHOM!”

7624102
I'm still in a Christmas mood, so here goes:

Never Ask Rarity If Your Santa Suit Looks Alright

“Never wear white after Labor Day?” Twilight asked. “An odd rule.”

“Gonna be tough convincing her,” Spike murmured, pointing at Rarity.

“Give it!” Rarity missed at grabbing Twilight’s Santa Hooves hat.

“You stop that! It’s for the foals!”

Up the street, Santa’s throne awaited with a long line. “Should get going, too,” Spike said.

“Never!” Rarity retorted.

“Gonna have a riot soon,” Spike observed.

“Let me have that!” Rarity magicked away Twilight’s hat and robe.

“You can’t take white from Hearth’s Warming!”

Down from her gem box, Rarity levitated a ruby.

“‘Never’ can be… manipulated,” she said, holding it out to him.

“Gonna… give me that?” At Rarity’s nod, he ate it.

“Run!” Twilight shouted.

Around a half-second later, a flame-ridden belch erupted.

And Rarity floated the white trim close until slightly charred.

Desert sand was all that remained of the robe’s glass buttons.

“You are welcome,” Rarity said. “Off-white.”

So, what rules were broken? Obviously, Rarity finessed her way around a fashion rule in-story. What about writing rules? Where to start... Having so many one-line paragraphs presents poorly, it's probably a bad idea to have three characters in a story this short, so many paragraphs have a repeated structure of "Dialogue," speaker said. It was kind of necessary to get it all to work out, though, which breaks another rule: having a dumb gimmick to your story. If you haven't spotted it yet, then read down the first word of each paragraph.

A nice variety of takes on the prompt so far; keep 'em coming, folks!

Four days to go!

7624102
This is a variation on something I had planned for a story I started writing but never finished or published. I liked the idea though and this month's prompt was a great way to share it.

It was nice of Discord to stop by to see how I was doing.  I wasn’t really hurt, it was just a little accident…but it was so sweet of him to show that he cares for his friends.  We sat on the couch and watched the animals scamper around the room.

He looked at me and asked, “Is there anything I can do for you, or anything you need?”

I thought for a moment and smiled.  “Could you show me some small chaos?”

Discord raised his right hand, grinned, and…

*SNAP*

Fluttershy looked at the room, her happy expression slowly turning to confusion.  She looked up at Discord and asked, “Discord, I…I can’t find the chaos.”

Discord grinned as he looked at Fluttershy.  “My dear Fluttershy, this is the best kind of chaos.  It’s so subtle that you won’t see it but many others will.”

Another good response this month, so thank you to everyone who's entered so far. If anyone else would like to have a go, then you have just over 24 hours remaining.

7624102
This one is not an entry... it's just for fun

"Nope!" said Big Macintosh while walking off screen.

7624363
The reality is silly on this: I did do that deliberately, but I then entirely forgot I'd done so until now! So I'm going to leave it. OTOH my lack of reply to FOME was my fault (Fimfiction glitched my reply and I was in a rush so didn't check) so apologies are due there. Anyway...

7624109 7624278 7624604 7624665 7625429 7625156 7625429 7626258 7626524 7632634 7633608

Writing implements down, please. Your time is up! Thank you as always to everyone who had a go.

I won't break the rules by taking 26 years to post the results, either. It'll be within the week. Feedback is open!

7634886
In the spirit of the contest of breaking the rules, I'm posting a story after it's closed (this is not an entry, it's just for fun)

Twilight’s eye twitched.

“So, after that happened, I put the ball over their on the table,” Pinkie Pie said to Discord.

One more hair of Twilight’s mane stood up.

“I sea what you mean.  You must be careful when playing with there toys,” Discord replied.

Twilight’s other eye twitched.

“I know, butt it was so fun to play with!” replied Pinkie.

Twilight’s neck twitched.  She stood up, yelled loudly, and ran out the door.

Discord handed a bit over to Pinkie. "You were right. That took much less time than I thought it would."

7624109
Sorry, but you kind of hit one of my pet peeves here. If you're going to have Luna do Ye Olde Speake, please research how to get it right. I guess this is AU? The pilot episode wouldn't have happened otherwise. I'm not sure what rule-breaking is going on, maybe just that Luna is in trouble in the first place for breaking the rules?

7624278
Amusing. I'm not sure what rule is being broken here either, though. Irresponsible magic use? Or abusing the "it was all a dream" trope?

7624604
Funny in a sort of farce way, though obviously not enough context to get an emotional connection from it. I'd guess the rule you're trying to break here is reaching for "easy feels"?

7624665
Definitely breaks lots of grammar rules, but I'm not sure that was intentional. There's an art to making sure that's obvious. Does break advice against fourth-wall stuff. On the amusing side.

7625156
Ooh, I like this. That last stark line is memorable. I do wish I had some context on why Luna might be convinced to think she wasn't doing anything with her life, though the general canon idea that she felt unappreciated can cover most of that. Like the other Luna story, the only rule breaking I can see is just NMM generally doing bad things.

7625429
Funniest of the humor ones I've read so far. Pinkie broke an obvious rule of common sense, and the writing breaks the rule of putting emojis in the text (though I'd argue that's not a net positive, as it doesn't add anything to the story).

7626258
Good thing you put the copyright notice there or I would have stolen it. Nice use of cringey LUS and metafiction. This would only work in a story this short, as it quickly gets annoying to read. It doesn't escalate the humor any, though, as the joke is already played out after the first sentence.

7626524
Ah, Twilight angry over Spike breaking a grammar rule and probably thinking he should have known better. Nice switcheroo, too. This was pretty funny.

7632634
Hack.

7633608
I must be missing something. If it's too subtle for Fluttershy to see, then why would it be so obvious to everyone else? He also claimed that it would help her. but I don't understand how it is. Or what rule is being broken. The writing's pretty good, but I just don't understand a lot about it.

7634601
Suits him, though again, I don't know what rule is being broken. I guess it might be implied that he's leaving because someone broke a rule?

7635121
The conceit itself is funny, though I'm confused as to how Twilight would know which homophone they were speaking. If they were writing these things, it'd be another matter.

7635377

Amusing. I'm not sure what rule is being broken here either, though. Irresponsible magic use? Or abusing the "it was all a dream" trope?

The rule being broken here is the old wives' tale saying, 'Never Wake Up a Sleepwalker'.

It's a new twist on a trope that I feel MLP would tackle if it wasn't restricted into teaching lessons.

7635377
Hi

In "A matter of perspective", Discord changes the story from first person perspective to third person perspective pretty abruptly

7624665
Logan: "Hey, I don't remember saying that!"

7635395
Oh, ok. I thought he had summoned a second copy of himself.

7635377
I was trying to go for Tell, Don’t Show.

7635469
Okay, got it. I hesitate to try citing things like that, because there are lots of different experience levels that participate in here, and it can be hard to tell whether being telly was intentional, so I shied away from identifying that as deliberate in case it wasn't and I came across as insulting the story. Just like I shied away from assuming grammatical problems were intentional, except for the one where they were the core of the joke (that is, they added to the story instead of just being there). And I'll tie in 7635395 here again and say these are good exemplars to budding authors out there of why "show, don't tell" and "don't change narrative perspective" are good rules. I of course don't fault you two for breaking them, since you did so on purpose to suit the rules, but both are hard to pull off well in such a way that they enhance the story and it's obvious to readers that it was intentional, not a mistake, that the author knew what they were doing and broke the rule to achieve a net-beneficial effect. Perspective shifts are incredibly hard to execute well (this one was fine because it's lampshaded as a gimmick), which is why authors are advised to stay far away from such tricks until they're very experienced.

7635562
Feel free to hit me with as many hard truths as you can find about me. My emotional scars are thick enough to withstand a tank shell.(That… That’s a joke.)

7635377

I guess this is AU? The pilot episode wouldn't have happened otherwise.

After 1000 years in the library, Luna has read all the books there are. She wished to return to being a princess, but nopony even remembered her. So, together with Celestia, they formed a plot of her 'return'.

As a Princess, Luna had responsibilities. Abandoning those responsibilities made her a rulebreaker.

This is not the results post. But I thought I'd (kinda) break the rules by doing something I almost never do and posting in the middle of the feedback period. Also, to post this as an (obviously) non-competitive entry on two counts. Title is sic, by the way:

Chapter 1
Yes Twi checked her latest letter,
But Twi checked she'd written nicely,
So Twi checked her letter oncely,
And Twi checked her letter twicely,
Yes Twi checked her letter thricely,
But Twi checked herself at fourcely,
So Twi checked the "uncheck" button,
And Twi checked she'd written horsely.

Actual results post coming later this week. Pray continue.

7624102

This story is NOT eligible to win Logan's Flashfic 150 contest (or any contest of my own.)

Early in the contest, I was delighted to see that people didn't seem to need an example story AT ALL. I'd still like to let people read my own "Break the Rules!" story, though.

Ponies Don't Have Fingers
(,Piles/ /of/ !!/Pretentious ;Punctuation!!!)

by MockingBirb

Beside Twilight was a cart. Its cloth cover hid her mysterious invention.

In front of Twilight sat three grumpy ponies, the All-Equestria Invention Contest judges.

Twilight announced, "I've built a typewriter for ponies!"

"Nonsense!" the contest's chief judge scoffed. "Writing Equestrian requires DOZENS of letters, so a typewriter needs DOZENS of keys. And hooves are so big, we simply can't fit enough keys onto a single typewriter. So Equestrian-language typewriters are impossible."

Twilight smiled. "Letter keys are overrated."

She yanked the cloth aside. Her invention looked like she'd scrambled three typewriters together, cut off all the human-style keys, and bolted on a few hoof-size paddles instead.

Twilight sat her plot upon a bench, pointing all four legs towards her mechanical monstrosity.

"Get out! Go away! Not another word!" the assistant judge warned.

Using all four hooves at once, Twilight banged out three lines at a time...using only small-print punctuation marks.

; ; ;-- ;   ;   ;--;    ;   ; ;--; ;-;  ;   ;-
;-; ;-- ;   ;   ;  ;    ; ; ; ;  ; ;-;  ;   ; ;
; ; ;-- ;-- ;-- ;--;    ;-;-; ;--; ;  ; ;-- ;- 

Author's Note:

https://wordcounter.net/ is the Flashfic 150 Contest's official word counter.

I broke Elmore Leonard's rule against sadisms (rule #3 at this link.) I think Leonard has a point, but on fimfiction.net, avoiding saidisms risks alienating some people.

Also, some people have a rule against sentence fragments.

But primarily, using punctuation marks to get 'free words' that aren't counted by the official word counter would usually (in most months) violate the spirit of the Flashfic 150 Contest rules, I think.

7636767 It probably took her over a minute to write "HELLO WORLD"

7636767
It's pretty impressive to reach precisely 150 words plus the "words". I'm also impressed by Twilight's planning at properly spacing everything in multiple lines!

Perhaps in this modern Internet age, a character-limit would seem more fair--no argument over different ways to count words, or if someone is cheating by adding em-dashes or unnecessary-hyphenation. (That hyphen was unnecessary).

7637084

I'm also impressed by Twilight's planning at properly spacing everything in multiple lines!

She doesn't have to PLAN it. That's why there are three typewriters combined into one, so she can type three lines at once. Three typewriters with three keys each (semicolon, hyphen, and space) makes a total of nine paddles, which I think a pony sitting corrrectly can handle with practice using hooves.

Evidently I did not make my thinking clear enough, since you are the second commenter of two to not just take this for granted. (Unless both of you are just joking about it, which would be fine I guess?)

I guess in her mind, it is just part of learning to type in Equestrian.

7637096
But she does have to plan it or else she would not be able to create the word art.

I am not criticizing that I think she could not plan it. I am noting that she had to conceive/imagine how all the semicolons, hyphens, and spaces would fit together to form the image of a word.

The idea that ponies would have something other than an alphabetic language system is reasonable. Or, at the very least, they might represent letters with something that requires less dexterity, like Dinotopia's foot language or what you (via Twilight) suggest here.

What I am a bit unsure about is why Twilight was using four hooves instead of three since there are only three typewriters. I guess you're suggesting a dance-dance-revolution style foot-organ? I didn't imagine nine paddles until you wrote it in the explanatory expansion above.

7635395

Yeah, but if you make it work too well, you might need an author's note to point it out. With a spoiler tag, I guess.

7624109 7624278 7624604 7624665 7625429 7625156 7625429 7626258 7626524 7632634 7633608

And it's results time!

I had a lot of fun with this month's entries, and I hope everyone else did as well. Also, my own little ineligible entry gave me the title Title is sic to use in a fic of my own one of these days weeks months years. Now, I was sorely tempted to break another rule by making everyone a winner this month, but that would be kind of tricky when it came to choosing February's prompt. Instead, two hon menshes and a winner.

Hon mensh 1: Pascoite for the sheer "oh no he didn't" audacity of that hidden message. Well no, not just for that, also for breaking a bunch of rules and still producing a very readable little story.
Hon mensh 2: KwirkyJ for that last line. Obviously not just that last line, as without the build-up it would have had little impact. But it was a real "oof" moment. Very nicely done.
Winner: SparklingTwilight for, well, everything. Not merely the hideous quantities of Lavender Unicorn Syndrome, but all the rest of it. The "all rights reserved!" bit breaks about three "rules" of ponyfic on its own. A story in two absurdly long sentences. Excessively purple language. (Obviously...) The footnote of course wasn't considered for judging purposes, but I'm guessing the asterisk that doesn't match anything in the rest of the post was also deliberate; if so, nicely done!

One final point, to scorpion1m: earlier, I was going to ask you to edit the story on the grounds it included a real person (me). However, Fimfiction rules do not ban real-person fanfic, as long as the Pony link is sufficient, so I let it stay. However, including a real person (other than public figures) in your fic without asking them itself breaks a "rule", so points for that, I guess!

Anyway, congratulations, SparklingTwilight! A win on your FF150 debut, too -- very well done. You now get to choose the prompt for February's contest. You're welcome to take a day or two to think about it, if you don't already have one ready. Once you do, please post it in this thread so that I can (hopefully) approve it and get it posted on the 1st.

Thank you again to everyone! It's been great fun. Feedback can of course continue!

7626524
7633608

I wrote about a couple of my favorite Flashfic 150 entries here. I hope anotheraccount doesn't mind having their contest entry called "both a success and a glorious failure," and a MOFA honorable mention.

I am still so happy to see so many people write good stories about my silly prompt idea!

7637374
7636767

Thank you very much! This was good fun.

I also want to thank Mockingbirb for designing the prompt and putting further effort into it by providing links (in another thread) on literary rules, etc. This prompt was near and dear to my heart since a number of my stories published on this site have intentionally poked fun at contest rules and regulations and included jokes about same, racing close to the line while providing (hopefully) entertaining tales! My entre-point to discovering this contest was Mockingbirb's blog.

Some of my favorites this month were (in order of posting, top to bottom):
Frazzle2Dazzle 7624604 (great ending subversion),
EileenSaysHi 7625429 (a big fan of the pictures, wish more stories would include them since we have a unique platform here),
ReedHoarse 7626524 (a riotous Twilight overreaction!),
Pascoite 7632634 (Rarity's cleverness!) ,
anotheraccount 7635121 (if Discord had been putting closed captions around the ponies, (which he certainly could do), the homophones would have made more sense--so I read it with that interpolated and found it amusing),
Mockingbirb 7636767 (Twilight's amusing mechanical artistry and intimate authorial knowledge of the word-count function!).

Thank you also for the kind comments! Very glad you enjoyed it, Loganberry.

I wish I could take credit for the asterisked footnote joke, but that was just record-keeping since I made the edits a few days after posting the story and I wanted to make sure that readers would know what changed and the asterisk was to draw attention to same like a bullet point rather than as a footnote.

There was however, at least one other missed rule in my bit... "fur" (I realize these are magical ponies and maybe they do have "fur", and I also realize there is some room for reasonable dispute on the issue. But standard ponies on Earth are not popularly or professionally considered to have fur). And I've seen multiple account-holders here complain when individuals reference "fur" instead of "hair" or "coat". (For additional 'rules of humour' touched on in my piece, see rambling reply to Pascoite below and look for rainbow and fluttershy).

Prompt Idea for Next Month: Bureaucracy. (A second option if that has been done before could be Religion, since I'm interested in seeing what religions the ponies get up to but that also could be a dangerous "third rail" and pretty hard to do in 150 words. I am, however, very excited to see pieces on "Bureaucracy", which is my first choice.

7635377

... This would only work in a story this short, as it quickly gets annoying to read. ...

Thank you for reading and taking time to consider others pieces. This contest allowed me to try out a Lavender Unicorn idea I had in my mind for a few months. We will see if the full concept ever gets developed into something longer.

It doesn't escalate the humor any, though, as the joke is already played out after the first sentence.

- In a sense I agree with the concern and maybe you just wanted to point it out to be helpful for future works (I agree it is definitely something authors should keep in mind when writing humour), but in a larger sense I disagree with any "rule" of the concern being a rigid one directly applicable here (of course, to the extent it reflects why it personally didn't segue with you--I understand(!)--one can certainly have preferences for different types of humour). I suspect I understand where you are coming from in the sense of one type of humour arising from the idea of rolling a snowball of "top that" moments, building momentum until terrible consequences explode. OR the other type of humour where there are expectations, expectations, more expectations, then they are subverted--at least one other story in this contest played amusingly with that paradigm.
--- There are multiple jokes. This story intentionally was a desperate existential dilemma. We don't know if Twilight will ever get out of the trap, and given that she's on a Möbius strip, she probably will not. That grim joke pops up later in the bit.
--- The first joke was one of extension--how far can the author take the concept of this... running gag. (while humour has a rule of threes, this multiplicity of descriptors for pony and purple went well beyond that ) The ending loop was intended to create a feeling of despair, a crushing feeling of emptiness, subverting typical expectations of a resolution to a story-structure , avoiding catharsis and applying unease which then switches on something in the soul to summon grim dark laughter.
- I also suspect you perhaps are cautioning against "gimmick" jokes that do not add anything to the tale and are not inherently integrated with same. I wouldn't blame you if you don't consider this a link since it isn't made obvious in the text (wanted to insert it but to also maintain the flow), but I envisioned a connection inherent in the Möbius strip's repetition. As the strip turns with Twilight's stroll through same, the writing changes. One cannot experience something without changing it slightly, so too with Twilight's hooves traveling inside the book does lavender morph to perse and other colors that are not quite exactly the same but that are considered synonyms.
--- For related reading, I recommend two stories by others on Haycartes' method. I prefer the shorter one--it takes a philosophical attitude to the situation. The longer one, although it did not grab me as much, certainly has scope/ambition and its topical content may appeal more to you than it did to me.

ETwilight Opens a Door

• MLP: FiM
• Comedy
• Thriller

Twilight Sparkle has a completely normal day in Ponyville.

• Twilight
• Spike

Golden Tassel · 6k words  ·  34  1 · 684 views

THaycartes' Pluperfect Method

• MLP: FiM
• Adventure

Twilight Sparkle has trapped herself in a shelf full of books. Will she survive- or will she lose herself to the story?

• Gore
• Violence
• Death
• Crossover
• Twilight

Kris Overstreet · 122k words  ·  159  7 · 2.1k views

Best Wishes!

7637500
Thank you! I'm pleased to say that we have not had "Bureaucracy" as a prompt before. As such, that's what we'll have next month. Thank you!

(Two thank yous, yes. Breaking another rule, that of proofreading my posts before I make them... )

7637599
Oh Logan, the month was to 'break the rules', not 'break my heart'. And I had everything planned for the month of love... by making it about villains.

But then again, bureaucrats are pretty much common day villains.

7637633 Challenge accepted.

For February, I'll write a story about love, villainy and bureaucracy. And I'm going to win the contest!

7637633
Love, bureaucracy and villainy? Casablanca did pretty well with that combination...

7626524
You just won yourself a follow. Not for the idea as much as for the execution.

7787838 Isn't necromancy against the rules? You're breaking the rules!

7787839
It's against the rules for me to obey the rules.