• Published 15th Nov 2013
  • 8,731 Views, 2,787 Comments

Cheerilee's Thousand - xjuggernaughtx



Cheerilee goes on one thousand terrible dates.

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PreviousChapters
Date Fifty-Nine - You Can't Spell 'Now' without 'Ow'

“Our lives are just so hectic, you know?” Gust swirled the wine in his glass while holding Cheerilee’s eyes with his own. “I just feel like it’s so important to live in the now. To really be here, you know, in the present, without any distractions.”

Cheerilee had to admit that she was feeling more than a little distracted. She’d seen Winter Wind’s father from time to time when he’d come by to pick the filly up from school, but he’d always looked so stern and imposing. When the pegasus foal had shyly come up to her a few days ago and said that her daddy wanted to speak with her, Cheerilee had wondered if Winter’s rather grim father had taken some issue with a recent lesson.

But she’d agreed; Winter’s education was the important thing after all. However, when Gust had touched down beside the jungle gym, he’d patted Winter on the head and told her to go play while he had a talk with Ms. Cheerilee.

Interesting! That’s what he called me! Cheerilee took a sip from her own glass. It wasn’t what he’d said, really. It was the way he’d said it. The hesitation behind the word. One that meant he’d really wanted to say something else. Alluring, maybe? Sexy? The mare who is just absolutely driving you crazy?

“But I think you’re different, Cheerilee. I can tell by the way Winter goes on about you.” Gust leaned forward just a little, his voice fervent. “It takes dedication to teach foals. You got to be right there with them. In their now.”

“Well, I try,” Cheerilee replied. The smoldering intensity of his gaze made it a little hard to follow the conversation. “Some foals struggle a little with their attention spans. You have to put yourself in their horseshoes. It’s no use planning an hour about ancient pony history when half the class will be looking out the windows. There’s plenty of time for that when they’re a little older.”

Gust grinned. “Exactly! There’s a time and place for everything, but I think when ponies are trying to make a connection, they should be in the present. Sometimes I think Equestria has just gotten too complicated. So many distractions.”

“Dad, can I go over to Sky Blaze’s? I’m all done with my—Whoa! What are you doing here, Ms. Cheerilee?”

Cheerilee started, nearly spilling her wine. She set her glass down on the table while running her other hoof through her mane a few times. “Oh, um, hi, Winter. How are you?”

Gust knocked a hoof against his forehead. “I’m so sorry, Cheerilee. I got so swept up in our conversation that I forgot to have Winter come in and say hello.”

“How did you get up here?” Winter said, squinting at Cheerilee for a moment before poking at the pillowy cloud floor? “I thought only pegasi could walk on clouds.”

Setting her hooves on her knees, Cheerilee leaned forward a little, putting her a little closer to the foal’s eye level. “Don’t you remember when we talked about Clover the Clever and what he did at the Great Tribal Summit?”

The foal thought for a moment before perking up. “Oh, yeah! The hospital spell!”

“Hospitality,” Cheerilee gently corrected. “And what did that do for pony-kind?”

Winter raised a hoof. “Oh, I know!”

“Winter, you don’t need to put your hoof up. You’re the only foal here.”

“Oh. Oh, right.” Winter’s pale blue cheeks darkened to a deep purple. “But, um, it made it so that other ponies could visit pegasus houses as long as they were invited. That way, the pegasi wouldn’t feel so lonely and we could all become better friends!”

“Very good!” Cheerilee said, clapping her hooves for the foal. “And as for how I got up here, your father carried me.”

“Dad’s strong!” Winter said, grinning. “This one time, he bought so many apples that—”

Gust cleared his throat. “Did you finish Ms. Cheerilee’s homework, Winter?”

“Yeah.” Winter fished through her tiny saddlebags for a moment before placing several pieces of parchment on the table. They were covered back and front with scrawling quill strokes. Cheerilee’s gaze traveled down the length of the page. From here, she could nearly read the foal’s answers.

Gust smiled a tight smile and nodded. “Good girl. And did you ask Moonbeam if you could come over?”

“Um, no, but Sky said that it would be okay ’cause his mom told him that I could come over whenever I wanted to.”

The tight smile retreated just a little. “Winter, what have I told you? You still have to ask. You can’t just show up.”

“But he said!”

Gust sighed. “Cheerilee, would you excuse me for a moment? I’d like to write a note to send along.”

Cheerilee ripped her eyes away from where the completed homework sat on the coffee table. “Huh?”

Gust paused for a moment, his expression tightening slightly. “I need to step away for a moment to write a note.”

“Oh, sure. No problem at all!” Cheerilee lifted her glass once more. “I have this excellent, um…” Her gaze dropped down to where the foal sat. “This delicious grape juice to entertain me.”

Winter rolled her eyes. “I know what wine is, Ms. Cheerilee.”

“That’s plenty of that tone, miss,” Gust said, prodding Winter out of the room. “I apologize for this. It will only take a second.”

“Mmhmm,” Cheerilee replied. Out of the corner of her eye, she could see the creamy parchment. As the sound of father and daughter receded, the assignment seemed to call to her. A hoof drifted over and pulled the sheet closer. What was the first question? Oh, that’s right. ‘Who was Equestria’s first princess?’ What did Winter put down for that? Princess Serenity! What a smartie! She got it right! Now, what about the next—

Hey!

Cheerilee jumped and let out a small scream. The crimson-inked quill that she hadn’t realized that she’d been holding dropped into her lap.

Gust placed a steadying hoof on her shoulder. “I’m sorry, Cheerilee.” I called your name three or four times, but you didn’t seem to hear me.”

Cheerilee felt the hot rush of blood in her cheeks. “I’m sorry, Gust. I was just lost in thought.”

“Happens to us all, I suppose. Anyway, where were we?” Gust said before pausing to think for a moment. “Ah, yes! The ‘Now!’” Scooping up his wine glass once more, Gust reclined into the couch and threw a foreleg out across the back. “I just find it concerning that everypony seems so caught up in what’s happening tomorrow that they miss today. I mean, sure, you can’t live without plans, but life isn’t meant to be nothing but, either. Have you studied any of Cantor’s writings?”

Cheerilee nodded. “Yes! I took a year of philosophy in college.”

“Then I’m sure you understand my concern,” Gust replied, grinning. “It was Cantor who first pointed out…”

Cheerilee took another sip, allowing the wine’s warmth to creep through her. She was doing her best to keep the dopey smile that she could feel inside from spreading too quickly across her face. Here she was, talking philosophy with this gorgeous hunk of a stallion for what might be three or four uninterrupted, secluded hours in a luxurious cloud house. Nothing here except the excellent wine, fine company, and the neatly stacked pages of Winter Wind’s homework, each page meticulously filled out in the neat hoofwriting that only little fillies seemed to possess. Now what was her second answer…

“Is something wrong?”

Cheerilee blinked several times at the hoof Gust was waving before her face. “What? Oh! Oh, I’m… I apologize, Gust. It’s just Winter’s homework caught my eye and I got a little lost thinking about the lesson plan.”

Gust’s look of concern cooled slightly. “And here I thought we were having a pleasant conversation.”

“We were! Are!” Cheerilee scooped up the pages, folded them, then tucked them into her saddlebag. “There. Wasn’t it Cantor himself who said that a mind free from distraction is a canvas upon which greatness is made?”

The rigidity seemed to melt out of Gust’s posture, and sank back into the couch once more. “It was! That was in his second essay on the workings of the mind. Now you’ve got me curious, Cheerilee. What did you take away from those writings? A lot of ponies seem to think that he was implying that physical fitness was subordinate to education, but I personally found it to be saying the opposite! For the mind to be at it’s best, the body must be in tip-top form, and that’s why the ‘Now’ is so important! We must be present, really listening to what our bodies need! Nourishment! Exercise! So many ponies are just cooped up all day in offices, skipping meals and missing sleep. Is that what you’re seeing, too?”

Cheerilee tipped her head to the side, thinking for a moment. “Well, yes and no. I do think that Cantor’s second essay implied pretty clearly that the mind wasn’t separate from the body, but he did take a rather solid stance on Winter Wind’s homework.”

“Excuse me?” Gust said, his brow furrowing.

Cheerilee shook herself. “A solid stance on the elevated role of education and mental stimulation, I mean. He didn’t want ponies to neglect their bodies, but it does say that a fit body housing an undeveloped mind is like a beautiful but empty vase.”

“Right, but—” Gust went to sip his wine, but noticed that the glass was empty. Glancing at Cheerilee’s glass, he rose. “Looks like we need a refill. I’ll be back in a moment.”

The moment that Gust disappeared into the kitchen, Cheerilee dove for her saddlebag. Okay, just one question! Pulling out the pages, she flattened them out of the table with one hoof while digging out her quill wit the other. Now what did she have for the second question? Oh… Cheerilee frowned. It was always like this with the wrong answers. Her heart just felt a little heavier. What could she have done to make the correct one a little more memorable?

Why did she think that Princess Serenity brought knowledge to Equestria? Her name is Serenity, for pony’s sake. She’s the embodiment of peace! I thought the photo I had of the Canterlot frieze made that pretty clear, but I guess not. Hmmm.

Her eyes traveling down the page, Cheerilee brightened. But she got question three right, and that was a hard one! Licking the tip of her quill, she made a check mark on the page, then scrawled ‘Good job!’ next to it. She must have just gotten Princess Serenity mixed up with her daughter.

Cheerilee shuffled the front page of parchment to the back with practiced ease and absently tapped the feathery tip of the quill against her chin as she read. Name three things that Princess Serenity did that still impact Equestria today. A treaty with the griffon empire. That’s good. The Canterlot garden statue? Where did she get that from? Well, I guess we do still have it today and was commissioned in honor of Serenity, but that’s not exactly what I was going for… Half credit. What’s her third?

Cheerilee’s eyes jerked from the page as Gust cleared his throat pointedly. Scowling, he had his forelegs folded across his chest. “I don’t think this is going to work out.”

“What? No, I—” Cheerilee crammed the partially-graded homework back into the saddlebag “—I just thought I’d get a little work done while you were away.”

“This is not the ‘Now’, Cheerilee. I thought you’d understand, but you’re not living the moment.”

Cheerilee grit her teeth momentarily. “I wanted to take a look at your daughter’s homework and so I did. What could be more ‘in the moment’ than that?”

“Us!” Gust replied, passing a hoof back and forth between them, “Here, making a connection!”

Cheerilee set her hoof on her hip. “Oh, so the ‘Now’ only counts when you’re involved?”

Gust squeezed his eyes closed for a second. “No, that’s not what I’m saying. I just think that you should be focusing on what’s important.”

“And that’s what here, exactly,” Cheerilee said, arching an eyebrow, “besides you?”

“Well…” Gust fidgeted for a moment. “Well, it is me, I guess, but I’m focusing on you because you’re the important thing to me.”

Cheerilee sighed. “Look, I’m sorry. I’m just… I have this thing about homework. I don’t like to leave papers ungraded, and they were right there!

“So what’s you're saying is that I’m always going to be second behind all of these distractions? Well, I’ve flown in that jetstream before. No thank you!”

Cheerilee hopped off the couch and scooped up her bag. “I don’t think you’re going to have to worry about that.”

Gust rose and made his way to the door. “No, I suppose that I won’t. I think you should go now.”

Cheerilee threaded the saddlebag’s tip through the buckle. “Well, that’s one thing we agree on, at lea—”

The rest of the sentence was lost in the skyfall. Cheerilee was suddenly plummeting down through the clouds while Gust’s wide-eyed, shocked face rapidly receded. She kicked and flailed, searching for anything at all to hold onto. Far away, she thought that she could hear Gust shouting, but the rushing wind and blood pounding in her ears made understanding it impossible.

After glancing down, Cheerilee wished that she hadn’t. Equestria was both dizzyingly far away and approaching too quickly for any level of comfort. She ripped her eyes away from the toy-like scenery and focused back where she’d come from. Gust, his form tiny, was straining to catch up to her.

He’ll never get here in time! Cheerilee flailed a bit more, but only ended up sending herself into a spin. The sky and ground flipped each other over and over again. The phrase “terminal velocity’ kept raising to the forefront of her thoughts. If I run into Clover the Clever in the afterlife, I’m going to kick him in the teeth for his hospit—OOF!”

Stars swam before Cheerilee’s eyes, and her tongue throbbed where she’d apparently bitten it during the impact. Below her, a pegasus was sputtering out surprised curses, but gasped when Cheerilee grabbed ahold with as much strength as she could muster.

“Why don’t you watch out where you’re flying, Cheerilee?” Rainbow coughed out. “You could hurt somep—wait.” Rainbow twisted her neck around to get a better look. “Cheerilee? What are you doing up here?”

“Falling to my death, or I was until I ran into you!” Cheerilee tightened her grip, and Rainbow’s eyes bulged. “Could you take me down to the ground now? I think I owe you a dinner or something.”

“Sure thing,” Rainbow’s voice sounded strained, “but maybe loosen up a little, okay? I can barely breathe. How did you even get up here.”

“Well, I was having a glass of wine with Gust, but he kicked me out of his house.”

“I didn’t kick you out!” Gust said, finally catching up. “We agreed that you should leave!”

Rainbow tucked Cheerilee under a foreleg, and set her other hoof on her hip. “You numbskull! Were you raised on the ground or something? Every pegasus knows better than that!”

“I forgot that she was an earth pony! I’ve never dated one before! I was living in the moment, you know? Really feeling that argument! I just—”

“Oh, here we go!” Rainbow rolled her eyes. “Gust is back ‘in the moment.’”

“Could we put the earth pony back onto the earth now?” Cheerilee said. Tucked as she was under Rainbow’s leg, she dangled uncomfortably. The wide jigsaw of Ponyville’s agricultural region was interrupted by things like cloudtop and the top of soaring birds. Things that Cheerilee was feeling distinctly unsettled to be seeing.

“Yeah, just give me a sec, alright?” Rainbow replied. “I gotta get a few things into Gust’s thick skull before we go.”

Gust scowled at Rainbow. “Look, it’s not my fault you can’t get over me. I’ve been telling you forever that you need to be in the present instead of wallowing in the past or wishing about the future.”

“Can’t get over you?” Cheerilee’s stomach lurched when Rainbow swooped down to poke a hoof into Gust’s chest. “Buddy, I was over you the minute I figured out all of your ‘Now’ stuff just meant do whatever you wanted to do.”

“What we wanted to do!” Gust replied, batting her hoof away. “There I was, trying to bring us together, and it was always, ‘Oh, I gotta go practice!’ or ‘I have time trials!’ or I need to help save Equestria!’ Where’s the time for actually living?”

Rainbow brushed her bangs aside to glare at the stallion. “Hey, just because I wanted to be somepony…”

Cheerilee sighed. Below, she thought she could make out the tiny specks of happy earth ponies trotting back and forth on whatever missions the day had chosen for them. She reached out for the ground. It seemed so far away, but somehow almost within her grasp. Isn’t that just life, though? You just try to keep putting one hoof in front of the other, but what good does that do you at thirty thousand feet?

Above her, the argument roared on, but something tickled at the back of Cheerilee’s mind. Twisting, she worked her hoof back to the clasp on her bag. As it opened, she snatched her red quill out of the air and pulled out Winter’s assignment. Licking the neb again and gripping the wind-rustled pages tightly, she let her eyes travel down the page to question four. Well, might as well make the best of the time...

PreviousChapters
Comments ( 56 )

It updated! YAY!

And is it gonna be Gust's fault? ... And Yes, it sorta is. But sorta Cherrilee's fault too!

Hospitality Spell is interesting. ... Twilight should really make it permanent or something.

... How much of Ponyville's Pegasus population has Gust dated? ... did Winter's mom leave 'cause of Gust's issues, or something else?

7850747 I actually wrote this specifically to be both of their faults. I don't think I've done that before, so I thought it would be interesting.

I'm not sure I completely understand the part with Winter asking permission to be...in her own house? Or does she live with her mother?

Anyway, this was a fun little trip. Never cared for the overly critical, full-of-themselves type, but then, I suppose Cheerilee should get her grading habit in order. Does Cheerilee's comment mean that there's a Rainbow Dash chapter in the future?

7850750

It is successfully interesting! Good for you! :pinkiehappy:

... How many of her students' relatives has she dated now... Apple Bloom, Winter, Diamond Tiara... Well, most of them are from married couples, so not many opportunities there, I guess?

Princess Serenity, and note at the naming customs reflecting the people! Always nice to see that lampshading or whatever!

I guess the Equestrian Royalty changed their naming customs from metals to qualities after the Unification. Or is it a Sailor Moon ref... Or both.

And possibly Luna and Celestia arrived a while after the Unification...

Interesting notes from Cherrilee's mind on how test-marking and marking works! Needing to make answers memorable.

Once a teacher, always a teacher.

7850775 She's asking to go over to Sky Blaze's house, who is a friend of hers. Moonbeam is Sky Blaze's mother's name.

Rainbow Dash chapter is probably likely. I mean, Cheerilee would need to date the whole of Equestria before this would be done...

Well I guess that spell means that Pegasus / other tribe divorces are simple, and rather terminal.

A hospitality spell huh, interesting. And it's such a shame, Gust seemed like such a nice stallion at first. :ajsleepy:

I'm incredibly to see more of this. :pinkiehappy:

I love the idea of the hospitality spell. It explains a lot of the handwaving the show does with cloud houses and it makes sense in context.

As for the date itself... yeah, Cheerilee's not blameless, but Gust is a pretty flagrant case of post hoc rationalization, and not just the usual gut reaction justification. It says something about someone when he crafts an entire personal philosophy (or at least misinterprets someone else's) to excuse his behavior.

At least Cheerilee's making good use of her time.

Oh, hey! You're back! We missed you, buddy! :twilightsmile:

And, well, it looks like Zephyr Breeze isn't the only one who a, makes passes and Rainbow, and b, can't take a hint. Though really, Cheers. Is during a date the best time to grade papers? You have to admit, some of this is on you. Silly, silly Cheeriliee. :ajsleepy:

7851166 Nah. He was just smooshed a bit. He went to the hospital.

Not Cheerilee's fault. It's what her cutie mark is telling her to do. Can't stop that.

7851038 Cheerilee can't help it! She has a grading problem!

And thank you. It's nice to be back. Hopefully I'll be able to continue on a semi-regular basis. I'm trying to write at least for an hour or two on the weekends.

7850985 She did indeed try to date a guard. It was date forty-five.

7850903 I generally have Cheerilee date ponies with serious personality problems, but I wanted to make this one kind of her fault, too. Also, it leaves me with an interesting weakness to play with in the future. Cheerilee just can't pass up ungraded homework.

7850890 They all seem that way at first. But they are all terrible. Or unlucky. Or terribly unlucky.

7850843 Luckily pegasi do have their own groups of patrolling guards to watch out for falling guests. One of the teams would have spotted Cheerilee eventually.

I hope...

7850786 I hear that Chris has the same issue. He just can't not grade papers.

r u shitting me there are no more chapters this triggers me

Will this whole story be 1000 chapters? I would to see that happen!

Mmmm mmmm, philosophical excuses for being a self absorbed dick.

7851279 Caramel is still the only one that makes sense after all this time :P

7850843 If your new pegasus wife insists on keeping the cloudhouse, you should definitely get a prenuptial with some rather strict codicils about death by falling and inheritance.

7851276 Like vampires and piles of seeds.

7851281

Well that eventually better have happened within about the next 30 seconds or so before Cheerilee hit the ground.

7851366 But remember an earlier chapter where she had six unlucky dates in a row? She could have multiple dates in the same week.

This was even better than I remembered. :pinkiehappy:

Pseudo-philosophers are even worse than actual philosophers. Even if Cheerilee is not blameless here, she did dodge a bullet by not making the relationship continue.

Dodged a bullet by falling nearly to her death, but dodged it nonetheless!

7851129 1000 chapters is actually the maximum limit. We know this because of https://www.fimfiction.net/story/149893/appledashery

7852400 Has anyone warned kudzuhaiku? The Chase doesn't feel like it could be wrapped up in an another sixty-some chapters.

7855046 You may have that honor if you like. I'm sure he'd be interested.

7855046 then he'll do a book two ^-^ and I aint complainin

Y'know, this story reminds me of another, older story that popped up on the featureds a little over two years ago. It's called "Help! I'm Trapped in a Shipping Card Game!" Ironically enough, it also features Cheerilee with a few other ponies as a pairing. However, this story is better because Cheerilee has individuality and its not a one shot! So yay!

Well, that was interesting.
I can understand Cheerilee getting distracted by the homework. Nice new history with the two pegasi.
The hospitality spell reminds me of vampires, honestly. So I guess public places that other ponies would be welcome anytime they're open? At least that probably trespassing on clouds if you're not a pegasus is hard.

This is my favorite thing in 2017 so far, please continue it!

Cheerilee grading papers while on the date reminds me of one of my firmest dating rules (back in the geological eras that applied) Never, ever date a woman with kids & a job -it just flat out doesn't work.

8124086 Seether00 would certainly agree. That guy can't get enough Gilda.

8127062 Yeah, it's not one of the better chapters. Sometimes the ideas don't come together as well as I'd like. I still think it's fine, but it's not a favorite.

8127093 Most of the ideas for the chapters are hilarious. The chapter that got me to like and favorite the story was Closed Encounters. it was the one that made me laugh the most, and I found Caramel to be the most likable of the dates so far. This one just felt like the backside of an early chapter -- at least that was my main issue.

And I hope this story is able to reach at least reach a hundred chapters. You're doing a really awesome job so far.

8127111 I'm very busy these days and mentally tired from my job. I'd like to keep this going, but I don't have much time these days. I'm hoping to get back into the groove once my work situation has calmed down some.

And Closed Encounters is one of my favorite chapters.

8134377 Inquisitor M is a challenging writer. He makes you work for you comprehension, but it's always in there if you can decipher it.

8133288 Caramel chapters are my favorite chapters to write.

8135310 They're my favorite to read. :derpytongue2:

Welp, finally done reading it! And pardon my french, but I wrote a review!

Now that I am completely caught up, I am eagerly awaiting the next Date.

I am looking forward to the ending though. I am holding out hope that there may eventually be a force behind these horrid dates, and it's not just left down to luck.
Perhaps it's a Zebracain curse or something, like, she has to go on one thousand terrible dates before she will ever have a good one. That would be an interesting ending.
It might even work out in the end, like, you write one final chapter, set about a month after her one thousandth date, and at this point she's stopped counting, believing she'd never make it to one thousand.
She goes out once more, and has a successful date, free of the curse.
I dunno, it was just something I thought of...

8291113 Unfortunately, I'm working twelve to fourteen hours a day at my job, so writing is pretty much a no-go for the time being. I'm hoping to get back to it in the future, though.

8295920
No problem, that's completely understandable.

Absolutely brilliant!
Made me laugh, made me sad for poor Cheerilee .
Some wonderful writing from both you and the guest authors, especially the Romance Reports reference. Hope you have the chance for some more soon

Random ideas for more bad dates...

A sexist
A pony in witness protection
A married pony wanting an affair
A pony who is into bondage
An underage pony

8544290
One who's REAALLLY into the fact that she's a teacher and asks her if she has a paddle...

Even if you don't come here any more, I'd just like to say thank you for making my 1,000th review such a fun one to write. Here's the fuller review, but in brief: very entertaining, and for the most part it rattles along at a fair old pace. Maybe the chapters get a bit long for my taste by the end, but that's a minor peeve. Definitely one I'm happy to fave! :pinkiehappy:

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