• Published 15th Nov 2013
  • 8,726 Views, 2,787 Comments

Cheerilee's Thousand - xjuggernaughtx



Cheerilee goes on one thousand terrible dates.

  • ...
19
 2,787
 8,726

PreviousChapters Next
Date Thirty-Four - Speed Dating (Guest Chapter by Metool Bard)

Guest chapter written by Metool Bard

Dear Ms. Cheerilee:

I have heard about your predicament, and I wanted to do something to help you out. I’ve taken the liberty of setting you up on a blind date with a good friend of mine. He’s someone you might be familiar with, actually.

His name is Crescent Moon, and he works for the Wonderbolts. I think you two will hit it off just fine. Meet him at his place at 17:00 (that’s 5:00 your time) if you’re interested.

~A friend

Cheerilee couldn’t help but read the anonymous letter over and over again as she walked through Ponyville. It had warning signs written all over it. Not only did she not know the pony who sent it (it could be a prank, for all she knew), but going on a blind date meant not knowing what to expect. And in Cheerilee’s experience, that was a recipe for disaster.

Even so, she had to admit that this Crescent Moon fellow seemed like a nice pony. She had often seen him flying around town while she was out at the marketplace. He certainly looked attractive enough and had an aura of politeness about him. Plus, he worked for the Wonderbolts; the most prestigious team of elite flyers in Equestria. The Wonderbolts wouldn’t hire just anypony to work for them. How weird could he be, really?

“I guess I’ll find out,” Cheerilee mused as she approached a small house at the edge of the town square. Pausing, she shook her head. “No, think positive, Cheerilee. Remember what happened the last time you let your paranoia get the better of you. He’s probably a swell guy, and we’ll both have a wonderful time together. If something completely unexpected doesn’t happen, that is…”

Cheerliee’s voice trailed away a she chewed at her bottom lip, a series of escalating disasters running through her imagination. As her heart began to pound, she tapped her forehead smartly with her hoof.

“No, don’t think about that,” she said. “Just focus on the present.”

After taking a while to get herself in the right mindset, she knocked on the door. Straight away, it flew open, revealing a handsome yet rather ragged-looking pegasus stallion.

“AhyoumustbeMsCheerileehowareyouI’mfinepleasecomeonin!” said the stallion in one breath.

Before Cheerilee could respond in any way, shape, or form, the stallion grabbed her shoulders and pulled her into the living room. Cheerilee hopped, barely avoiding a mountain of paper laying on the floor. Everywhere she looked, timesheets, calendars, and events planners were piled in precarious stacks. Every inch of the wall space seemed to have stats and charts pinned on it, and an overabundance of clocks of all shapes and sizes ticked out a mad rhythm.

“Pleasepleasehaveaseat!” said the stallion, gesturing to a blue couch behind Cheerilee.

“Oh. Well, thank you,” said Cheerilee, still having difficulty processing the situation. “Um, you wouldn’t happen to be Crescent Moon, would you?”

“IndeedIam,” said the stallion. “AndmayIsayit’sapleasureto…”

“Hold on, hold on,” interrupted Cheerilee, raising her hoof. “Could you... slow down a bit? I’m having trouble keeping up.”

“Hmm? Ohrightsorry,” said the stallion, taking a deep breath. “I’m just in such a rush right now. Anyway, as I was saying, it’s a pleasure to finally meet you in person.”

“Um, likewise, I guess,” said Cheerilee, rubbing the back of her head sheepishly. “Uh, Crescent… Do you mind if I call you Crescent?”

“Not at all, not at all! It saves time,” said Crescent. “So, I was thinking we could go somewhere nice for dinner.”

Cheerilee’s expression brightened. “Oh, well that sounds…”

“Wait, sorry. Nix that idea,” said Crescent, looking at one of the calendars on the wall. “I forgot that I have something important tomorrow morning. I can’t go out to dinner. How about a movie instead?”

“Oh. Okay,” said Cheerilee. “I’m actually interested in seeing…”

“Wait, wait! No, we can’t do that, either,” interrupted Crescent, checking another schedule. “I have to go through academy applications later this evening. I don’t have time for a movie. How about we just sit here and talk?”

Cheerilee blinked in confusion. If we’re not going out, then why did you bring up the possibility in the first place?! she thought. She took a deep breath and let her rage dissipate in a great sigh.

“That... actually sounds quite nice,” she said. “After all, nothing crazy can happen in the safety of one’s own home.”

Crescent raised an eyebrow. “What do you mean by that?”

“Nothing!” said Cheerilee, hastily casting her gaze upward. After a few awkward seconds, she cleared her throat. “So, I hear that you work for the Wonderbolts.”

“Yes, indeed. I am the Wonderbolts’ official caretaker,” said Crescent Moon, taking a seat next to Cheerilee.

Cheerilee tilted her head. “Caretaker?”

“Yes, you’re not the first pony to get confused by that,” said Crescent with a lighthearted chuckle. “Really, all it means is that I’m responsible for everything that happens behind-the-scenes. I sort their mail; keep their schedules; go through paperwork. You know, that sort of thing.”

“I see,” said Cheerilee, looking around at all the schedules. “So, that’s what this is all about?”

“More or less,” said Crescent with a shrug. “I like to keep myself organized. Believe me, staying on top of all this is hard work, and it’s a job I take very seriously.”

“I can imagine,” said Cheerilee with a giggle. “Actually, the foals I work with keep me on the run, too. I’m actually lucky to be catching a break like this.”

“Mmm. You don’t say,” said Crescent with a nod. “I admire a pony who’s a hard worker. It’s nice that we have something in…”

Cheerliee jumped as the clock at her elbow began to ring.

Crescent held up a hoof, smiling apologetically. “Hold on a moment. I need to proofread Spitfire’s opening speech for the Q&A panel the Wonderbolts are hosting later this week. Back in a jiffy.”

Before Cheerilee could say anything, he dashed off into another room. After a few seconds, he returned.

“There we are. All done,” he said. “Now then, what was it we were talking about?”

“Uh, that you admire hard workers,” said Cheerilee. “Um, Crescent, don’t you think you could’ve done that before our date?”

“Well, that was the plan,” said Crescent. “However, this date was very last-minute, and I had to rearrange my entire schedule. Honestly, I’m way behind as it is.”

“Well, what were you doing before I got here?”

“Getting my place ready for your arrival.”

Cheerilee took a quick look around. Indeed, the living room was extremely neat and tidy, with the exception of all the schedules lining the walls and the papers on the floor. But apart from that, there wasn’t a speck of dirt or dust to be found anywhere. Even the papers were stacked into nice, neat piles.

“Wow. So I see,” said Cheerilee. “Still, you should probably…”

Another clock’s alarm went off. “Hold that thought, Cheerilee. I have to alphabetize the roster for the next Wonderbolt Derby,” said Crescent. With that, he took off again.

“Alphabetize the roster?” Cheerilee wondered aloud.

In a few seconds, Crescent returned again. “So sorry about that,” he sighed. “Now then, you were saying?”

“I was saying that maybe you should consider taking a vacation,” said Cheerilee.

Crescent blinked. “What’re you talking about? I am on vacation.”

Cheerilee’s eyes went wide. “You are on vacation?” she parroted.

“Just as I said,” said Crescent. “Although Captain Spitfire says that I have no grasp of the concept. She’s actually quite a kidder, believe it or not.”

I… don’t think she’s kidding, was what Cheerilee wanted to say. Instead, she forced a smile and said, “So, you get along with Spitfire, I take it?”

“Oh, of course,” said Crescent. “Captain Spitfire is a great boss. She even set up this date for me.”

Cheerilee’s jaw dropped. “Wait, Spitfire set this up?!” she exclaimed.

“In part,” said Crescent. “She said she was worried about me burning myself out or something, and that I had to separate my work life from my social life. Honestly, I have no idea what she’s talking about.”

I think I can hazard a guess, thought Cheerilee.

“So, she suggested that I go out on a date, I heard you were in the market for a special somepony, and we coordinated our efforts from there,” Crescent continued. He looked around nervously for a moment before leaning in close to Cheerilee and dipping his voice. “Just, don’t tell anypony about it, alright? Captain Spitfire doesn’t need the publicity.”

“Noted,” said Cheerilee with a nod. “Um, listen, Crescent. Maybe you should…”

Once again, she was interrupted by an alarm going off.

“Just a moment,” said Crescent, darting into the kitchen.

“Oh, what now?” Cheerilee groused.

In a matter of seconds, Crescent came back with two mugs.

“How about a cup of tea before you have to go?” he asked.

Cheerilee looked at one of the clocks on the wall. It was only ten after five.

“Um, Crescent. I just got here,” she said.

“Time waits for nopony, Cheerilee,” said Crescent with a shrug.

Finding herself unable to argue, Cheerilee stared blankly at the stallion for a moment before taking the cup, frowning. Taking a sip, she fought to keep herself from spitting it back into the cup. “Crescent, this tea is cold!”

“Hey, heating takes time!” Crescent exclaimed defensively. “And that’s time I don’t have!”

Before Cheerilee could point out how ridiculous that was, she found herself being shoved out the door.

“ThankyouverymuchCheerilee,” said Crescent. “Ireallyhadawonderfultime. Weshoulddothisagainsomeday. WellI’dbettergoresearchthatpierecipeSurprisewantedmetolookintoforSoarin’sbirthdaygoodbye!”

With that, he slammed the door.

“Er... Bye, Crescent,” said Cheerilee. She then started for home, wondering what had just happened.

I… I think that was my best date in weeks, Cheerilee thought, staring back at the door. Maybe I should send Spitfire a thank you card…

PreviousChapters Next