Episode 18: Dr. Whooves on the Daily Show

The wind blowing against his face was no longer that of the nature’s natural flow but from the wings of a lone figure hovering on high, looking down on Jon. At first he heard the sound of flapping wings but didn’t give it much thought, with the assumption being that it was a bird on its merry way.

But soon Jon would be awoken from his moment of silent meditation by that very same guardian angel addressing him. Slowly this lone figure opened her mouth to announce her arrival. However instead of the perfectly pitched angelic voice one would reasonably expect from a servant of the almighty, this particular angle spoke in a muffled and quazzy tone which was difficult to hear but still loud enough to get Jon to open his eyes.

“I brought you a letter!” she screamed, causing Jon to jolt in surprise whereupon he rammed the top of his head on the side of something metallic, making a loud banging noise like someone hitting the side of a shed with a frying pan.

“ARGH! Son of a bitch!” Jon yelled as he grabbed his head with both his hands, his karmic pain going up and down his spine. “Hey buddy what’s the big ide--”

The sight before him made the famous TV host stop and stare in shock and complete disregard for his own throbbing head. In his time spent in Equestria he had seen many different wonders, from Pegasi and Unicorns to Minotaurs and Dragons (all of which could talk) with magical abilities he thought impossible.

But nothing could have prepared him for what he was currently beholding, for it was the strangest thing he had seen to date. A floating mailbox, hovering just over head as if possessed by Lord Voldemort himself.

But this wasn’t any ordinary mailbox, but one with its own body. Yes the more Jon looked upon this seemingly haunted item the more he noticed some telltale signs of organic life, like the fact that it had a body, legs, tail, and the most glaringly of all a pair of wings keeping it afloat.

Body of a Pegasus and head of mailbox; Jon was starting to get a clear idea of what he was dealing with, or rather, who he was dealing with. Without even checking the Cutie Mark of this sudden individual he already concluded as to who it was, so to confirm his suspicions he tentatively reached forward to grab the lid of the mailbox, whereupon he opened it to see for himself what contents it concealed.

What he saw wasn’t a letter, as one would assume would be in a mailbox, but the head of a pony looking straight at him, her blonde mane covering most of her face. Though Jon knew what he was looking at, his suspicions were undoubtedly confirmed when he saw a pair of eyes that seemed to be looking in any direction but forward.

“Hello Mr. Stewbert!” she announced.

“... Derpy,” Jon sighed. “Fancy seeing you again so soon.”

There was always a special place in Jon’s heart for Derpy. Her childish innocence and limited understanding of what was going on around her were matched only by her loving nature and respectful disposition. However it was her simplistic nature that also made it somewhat of a chore to talk to her, where at any moment she’ll space out, or forget who she was or what she was doing. Jon loved Derpy but right now he was in no mood to be dealing with her.

“Hey, hey, hey!” she struggled to get his attention. “Guess what, guess what, guess what, guess what, guess what!”

“... What?” Jon forced himself to answer as he got up to dust himself off.

“NO! You have to guess!” Derpy demanded. Turning his head to the side Jon glanced over at the two patrolling guards to see if they would do anything about this. Both of them just responded with a weak shrug of the shoulders.

“Okay uh, let me see,” he humored her. “You brought me a le--”

“I BROUGHT YOU A LETTER!” she announced with a level of enthusiasm as if this was her first day on the job, something which (given her short term, and long term memory problem) Jon feared she might truly believe.

“Gee, you don’t say,” he added as he got up to his feet only to try and sidestep her. “Well that’s nice but I really should--”

“Wait! I didn’t give it to ya yet!” she exclaimed as she flew in front of him, blocking his path. The momentum of her brief redirection caused the door of the mailbox to slam shut over her face, transforming her once again to her previous form. “Hey?... where did you go?”

Jon’s frustration had reached its tipping point; he seriously didn’t have time for this. Thinking that perhaps he could escape, Jon formulated a plan to tip-toe around his confused friend and make a break for Canterlot City. However the thought of leaving Derpy in such a state made him feel guilty, after all she wasn’t the one who had let him down. Again, Jon felt frustrated.

“Okay, you know what!?” Jon exclaimed as he reached forward and grabbed Derpy with both hands. Quickly he tucked the wayward delivery mare under his arm like a football, and with his free arm grabbed the mailbox and in one motion yanked it off her head, messing up her already messy hair.

Letting go of her, Jon watched as both she and the letter she was carrying fell to the ground, apparently she had the mail tucked under her head.

Holding the mailbox in his hand, Jon found himself looking over at the castle, imagining where he thought Celestia would be and, out of left over anger, tossed it at one of the open Castle windows. His aim was spot on, but what he didn’t know was he had chucked the metal compartment into the nurse’s lounge, where it terminated on the head of the nurse who was previously looking after Trixie.

While this was happening a delirious (more so than usual) Derpy watched as the small piece of paper that was previously in the mailbox fluttered down and landed on her nose. Her eyes adjusted on it in rare synchronization and her brain jump started, reminding her of why she was here.

“OH THAT’S RIGHT!” she yelled, as she grabbed the letter and burst upwards like a rocket.

“GAH!” Jon screeched, surprised by Derpy’s sudden outburst. “Don’t do that!”

“Oops, my bad,” she apologized as Jon grabbed his heart. “But I’m just so excited because I just remembered that... I BROUGHT YOU A--”

Reaching forward Jon threw his palm across her face, his hand large enough that he was able to grab her head while at the same time silencing her.

“I know,” Jon grunted as he snatched the letter from her hooves. “You brought me a letter.”

“How did you know!?” Derpy earnestly asked once Jon released her. Ignoring her, Jon tore open his envelope and without looking grabbed the first thing he felt out which was indeed a letter. With a flick of his wrist he unfurled the piece of paper to reveal a row of boxes with corresponding letters and subjects. Adjusting his eyes to account for his lack of reading glasses, which he forgot he had in his pocket, he began to read the letter out loud.

“‘Social studies: B+, Math: A-, Science: C+, English: A+ PE... wait, what the hell is this?” Jon wondered out loud as he skipped the middle portion to bottom section where it had more writing. “‘Young Nathan has shown a great improvement in his math and english subjects but still continued to struggle with science and...’”

The letter went on to describe about how the school provided tutoring services for all ages and how the next parent-teacher conference was in a few weeks. Glancing upward at the logo of the school that his son went to, Jon finally reached the correct answer.

“This is... this is my son's report card,” he concluded.

“That’s right!” Derpy said. “A nice man in Ponyville told me to bring this to you! It took me a few days but I finally found ya!”

Temporarily ignoring the fact that it was Jon himself who had sent the letter, there was something more immediately pressing that had him almost speechless.

“You mean you... you actually did your job?” he asked in utter shock.

“I sure did!” she proudly announced. “I always promise to do my job the best I can! Rain or shine, snow or feet, I deliver your mail!”

“It’s ‘sleet,’” Jon corrected.

“Wah?” asked Derpy.

“The motto you’re thinking of is ‘Rain or shine, snow or sleet!’” he emphasized. “It’s sleet, not feet.”

“What are feet?” asked Derpy.

“Just... nevermind,” Jon said. Even in her confused state Derpy looked happy with herself for doing her job, which didn’t help Jon one bit.

Seeing her sheer determination made Jon feel somewhat guilty for his actions. The last time he was in Equestria he was trying to sneak into the castle but ended up going to the spa with Rarity. Along the way he met Derpy and, much like right now, tried to get rid of her by giving her an obviously fake delivery which she took just as seriously as anything else.

“Yeah... uh listen Derpy, I’m sorry for wasting your time,” Jon admitted as he placed the report card and the envelope that it came in inside his pocket. “I shouldn't have sent you on a wild goose chase like that.”

“What goose?” she asked. “I was just doing my duty as the mail mare!”

“Well all the same I shouldn't have given you that letter in the first place,” he continued.

“Oh youse just a big silly!” Derpy chuckled as she tussled Jon’s hair. “You didn’t give me the letter! That weird guy did!”

“Derpy... that weird guy was me!” Jon revealed, feeling slightly offended.

“... Wah?” she responded as if she was given a particularly difficult math problem.

“Jesus Derpy!” he exclaimed. “How do you not remember that the guy who gave you the letter is the same guy who you delivered it to!?”

“Ooooooh I get it now!” she exclaimed before tilting her head to the side again. “You must be the weird guy’s twin brother!”

“No! Derpy I... okay, how am I weird? I-I mean I... I don’t have a twin brother!” he exclaimed, his back and forth with her making him frustrated all over again. “It’s me your friend... Jon... Jon Stewart!? Come on, I know you remember me.”

“I love Jon Stewart!” she exclaimed as if she was talking about him rather than to him. “I watch that guy’s show everyday... I’ve always wanted to meet him.”

As if he lost control of his lower jaw, Jon’s mouth dropped, where it would stay for several seconds as his mind tried to compute what was happening.

“Derpy I... Derpy I am Jon Stewart!” he exclaimed. “For God sake I had you on my show once before! Don’t you remember!?”

“Um... I... I don’t know,” she guilty confessed.

“You... I mean you... how can...nevermind,” Jon sighed as he turned his head back to glimpse at the castle, then at Derpy who was rubbing her head. “Do you at least remember how you got that mailbox stuck on your head?”

“... What mailbox?” Derpy asked.

Feeling like he had lost an impossible battle, Jon stood and marveled at the advanced level of ignorance from this one individual. Taking advantage of this momentary bout of silence, Jon quickly inhaled and with deep breath threw his hands in the air as if to say “I give up” and then proceeded to walk forward down the path that lead towards Canterlot City.

The road that lead from Canterlot Castle to Canterlot proper was a long stretch of scenery that was purposely left mostly untouched, aside from the cobblestone road and occasional bench. Being the only path leading into Canterlot, with its abundance of fields which eventually dipped into the lower section of the area, as well as the castle itself being built on the side of a mountain, the whole stretch of land would give Canterlot a strategic advantage should it be caught in a war, but nowadays is recognized only for its mosaic nature. There weren’t many trees on the road to Canterlot City, which gave Jon a good view of the surrounding fields, and he could guess where their parameters lie.

This was rather therapeutic for Jon since the scenery was luscious enough to somewhat calm his still trembling mind. However there was now another factor eating at him, and that was although Jon was done talking with Derpy, she wasn’t yet done talking with him.

“Where ya going?” she asked with an innocent smile as she hovered just overhead.

“Heading into town,” he answered as he increased his speed.

“Why?” she asked.

“Because I need to find someone who can help me,” he answered once more.

“Why?” she asked.

“Because my friend is in trouble,” he answered, now getting annoyed.

“Why?” she asked.

“Because she’s sick,” he gritted.

“Why?” she asked.

“Because mind your own business that’s why,” Jon barked in her direction. Given what he’d been through today, Jon wouldn't usually have felt guilty about snapping at Derpy, but the look she gave in response sent a jolt of regret right through his heart. To Jon she was the essence of innocence, so when she scrunched her nose and lowered her head with a face like she was about to cry it made him feel horrible inside, sick even.

“A-are you mad at me?” she sniffed, which only made Jon feel worse.

“N-no, no, no, no, no I’m not, Derpy,” Jon confessed as he stopped to face her with a saddened expression of his own. “It's been a rough day and I’m just... I’m just really sad right now.”

As if their brief altercation never happened, Derpy immediately perked up and patted Jon on the head.

“Well then I have just the thing for you!” she proudly announced as she buried her head into her mailbag, littering the ground with several sealed letters in the process.

Eventually she emerged with some kind of pastry half in and half out of her mouth. Jon recognized this culinary treat all too well.

“Hearf ew pho!” she mumbled before plopping a saliva spattered muffin into Jon’s hands. “This will cheer you up. It’s the last one I have and I was going to eat it for lunch... but you can have it.”

As unappetizing as it looked, with half of it dented from her teeth, Jon was still greatly moved by her simple gesture. It was touching because although to him it was just a plain looking snack he knew that to Derpy it meant so much more.

“Thanks Derpy,” Jon smiled as he continued to walk down the path with muffin in hand. “I’ll uh... I’ll eat it later.”

“Oh, oh, oh, maybe you can give a muffin to your sick friend,” she offered. “I bet that would make her happy.”

“I don’t think that’s going to help her much. Her illness is something that... well, requires a more technical approach,” Jon countered as Derpy flew in closer. “Muffins aren’t the answer to everything my young Padawan... someday you’ll realize this.”

As the two passed by a tree which momentarily gave them some shade, Derpy sported a look on her face like Jon was talking crazy.

“But muffins make everything better!” she argued. “Mama said so herself.”

Jon momentarily recalled how Derpy’s mother was the one who originally got her obsessed with the culinary treat. He remembered how during the interview she explained that whenever she was picked on for being different her mom would whip up a batch to cheer her up.

“Ah yes, that’s right,” Jon commented, determined to carry the conversation further as a distraction. “But tell me Derpy... have you ever been so sad that even muffins didn’t help?”

This was actually a question he wanted to ask her during their first encounter, when he had her on the show for an interview. At the time he didn’t ask it because he felt it might be too sad a topic to delve into on only his second interview with an Equestrian citizen.

As he predicted back then, the question itself proved to be so powerful that it caused Derpy to stop in her tracks. Realizing that he was no longer being followed, Jon turned to find her just floating in place, stationary in the air as she began to think carefully for an answer.

“Um... well... sometimes,” she guilty answered. “Sometimes when I’m really, really, really, really, really sad I don’t feel like making any muffins.”

“I see,” he commented as he motioned for her to continue down the road. “Might I ask what you do to cheer yourself up if such a scenario occurs?”

Without Jon noticing, Derpy’s frown turned upside down, and it wasn’t because she was flying at a weird angle. She knew the answer to Jon’s question, the mere thought of which placed a bright smile on her face.

“That’s an easy one!” she giggled, as her face turned a shade of red. “Whenever I’m sad, and muffins won’t help, I just talk to the bestest, kindest, most huggable, sweetest pony to ever live.”

“Who, Applejack?” he jokingly asked.

“No you silly filly!” she chuckled. “I’m talking about my husband... Mr. Whooves.”

This was definitely a side of her that Jon hadn’t seen before, he wanted to see more of it, too.

“Oh you’re married huh? Well, join the club,” Jon commented as he flashed his wedding band.

“What the!? I didn’t know there was a club!” she exclaimed and Jon continued to flex his fingers in the air to show off his proof of marriage.

“There sure is, we get together every Thursday to come up with new and inventive ways to annoy single people,” Jon chuckled. “You know it’s funny... I always pictured you as the single mother type.”

“Nope! Me and my husband raise Dinky together!” she replied.

“What’s he like?” Jon asked.

“Oh, he’s the bestest ever!” Derpy roared as she tried to hide her still blushing face. “He’s always nice to me and he always makes sure Dinky goes to bed on time if I’m out late. He knows just the right way to rub my head to make it feel good and, and, and, this one time he made my favorite breakfast ‘cause it was my birthday.”

“Wow... he sounds like a real upstanding kind of guy,” Jon commented. “Seems like you bagged yourself a real keeper.”

“I sure did! He’s my favorite pony ever!” she squealed as she did a quick loop in the air. “I love him sooooo much! I’m so lucky to be married to someone like him! He's the best pony, husband, father, doctor and friend a girl could ever--”

This time it was Jon who stopped walking midway, only he didn’t stay still for long. Quickly he turned around to face his floating friend with a face like he’d seen a ghost.

“WAIT WHAT!?” Jon roared, interrupting Derpy and startling her so suddenly she forgot how to fly. “'Doctor!?"' Did you say... y-you’re married to a doctor!?”

“I am?” Derpy commented, still stunned from Jon’s outburst. Familiar with how her mind worked (something which terrified him) Jon immediately ran up to Derpy and grabbed her head with both hands and drew her in close.

“Derpy... look at me... look at me... now with both eyes,” Jon demanded, his request being met head on by his feathered friend now looking into his eyes. “Good... now then, I want you to listen very, very carefully. This husband of yours... what kind of doctor is he?”

“He’s the best kind!” she answered. “He can do anything! This one time I was real sick and he made me feel all better.”

“Okay, okay so he deals with medicine then!?” Jon continued. “So he’s like an psychian?”

“Um... I think so,” Derpy answered, her understanding of the subject spotty at best.

“Okay... now try to answer this next question as best as you can,” he continued. “Can your husband perform or at least know anyone that can perform an Entropy spell? I’m looking... for someone who knows how deal with Clausus syndrome... can your husband help me with that!?”

With excitement Derpy began to flap her wings, though since Jon still had a firm hold on her head all she managed to do was raise her body a few inches upwards.

“Well sure he could!” Derpy assumed. “My husband can do anything!”

Ordinary Jon would have been highly skeptical of Derpy’s claims, as far as he knew she didn’t have a husband, let alone one that could specifically help him. Her claims seemed too good to be true but Jon was so desperate for help that he blindly took her answer at face value.

“Perfect!” he exclaimed with joy as he threw his hands in the air, momentarily sending Derpy floating away. “Okay Derpy, I need you to do me a big favor! I need you to get your husband and tell him that I want to meet with him. I need to set an appointment with him... do you think you can do that for me?”

“Weeeell... I don’t know,” she responded as she rubbed the back of her head. “I still have to deliver a whole heap of mail and Ponyville isn’t on my route just yet.”

Tilting his head to the side, Jon was confused to see her responsibility for her work at a time like this, since she had been slowly leaving a trail of abandoned letters like Hansel and Gretel leaving bread crumbs to get back home.

“Tell ya what,” he said as he raised his hand with the muffin that she herself had given to him. “You set up a meeting between me and your husband and I’ll give you this muffin, right here, right now.”

Strolling through the verdant scenery with the innocent Derpy had mellowed out Jon somewhat. He was still anxiety ridden and upset with Celestia, but his mind was clear enough to break through Derpy’s web of logic. His plan worked.

“DEAL!” Derpy roared as she snatched the muffin from his hand and plopped it in her bag. “Oh yummers! Now I have two muffins for lunch!”

Shaking his head, Jon rubbed his hands together to get rid of the combination of drool and crumbs left behind by his once acquired soggy treat.

“Alright, so what’s the best way to meet up with Mr. Whooves,” Jon asked. “Should I just follow you to your place or what?”

“Nope! I need to go talk with him first! He doesn’t really like guests coming over,” she explained. “Oh! I know, I’ll tell him to meet you at his favorite restaurant! It’s this place near our house.”

“That’ll work, I could use a bite to eat actually,” he admitted. “What’s this joint called?”

“Uuuum... I forget,” she said.

“Of course you have,” Jon commented.

“Don’t worry, it’s really easy to find!” she explained. “It’s the one with the red roof and white fence out front.”

“Alright, I’ll find it. Well I think we all have our homework assignments for the day!” Jon said before clasping his hands. “You go get your husband and I’ll meet him at that restaurant. Okay, break!”

“Break what?” Derpy asked.

Ignoring her, Jon continued down the path to Canterlot, only now he knew exactly where to go. He would go to the lower end of the city to catch a tram ride all the way down to Ponyville. From there he would be one location away from getting what he needed.

As he went over in his head his pitch for when he finally met with Derpy’s doctor husband, he was cut off by Derpy herself flying in front of him, blocking off his path.

“Uh, Derpy... I don’t want to sound rude but... shouldn't you be off getting your husband right now?” he asked.

“Don’t worry I will,” she assured him. “It’s just... before I go... can I... can I have your autograph!?”

At this point Jon was willing to part with anything if it meant he would be one step closer to saving his friend. So to him a quick signature was both simple and to this day still oddly flattering.

“Yeah sure,” he agreed as he reached into his jacket pocket to retrieve a sharpie.

“YAY!” she chirped, as she did a quick backflip to show off her excitement.

“Do you have a piece of paper?” he asked though he didn’t get a response with Derpy still fidgeting with giddy anticipation. Jon waited for her to produce something worthy enough for him to scribble over, with him convinced that she would use someone’s letter as stationary.

With arm stretched out ready to sign, Jon watched as Derpy just flew in place, too exciting about her soon to be acquired autograph to actually produce something to write on. Jon considered himself to be a patient man but even he had his limits, so to get things back on track he quickly signed his name across Derpy’s forehead.

“There ya go!” He placed his pen back in his coat. “Now will you get your hubby?”

“You bet I will!” she exclaimed as she rocketed off to her left, leaving a trail of envelopes in her wake. She flew off so fast Jon barely had time to follow her movement, but he did hear a loud noise like someone crashing into a hedge bush. Following the trail of sealed letters on the ground, Jon saw that Derpy had blindly flown into the side of a tree, her head now stuck in its trunk.

“Well, that solves the mystery of the mailbox,” Jon said as he walked up to the tree to lean on it, turning his attention now on the still stuck Pegasus. “Need any help, Derpy?”

Although she did respond he could not make out what she was saying.

“Okay, here comes Mr. Muscle,” he said as he effortlessly pulled Derpy from her branchy prison.

“Thanks!” she chimed with embarrassment as she stuck out her tongue out. “It was dark in there.”

“Don’t mention it,” Jon said.

Walking a few feet forward to the edge of the cliff, Jon lifted Derpy in the air Lion King style to show her the scenery before them, which contained Ponyville several miles below.

“See that Derpy?” he asked. “What’s that town called?”

“That’s Ponyville!” she answered.

“Good job!” he complimented. “And what are you going to do once you get there?”

“Imma get my husband and uh,” she stammered, trying to remember. “OH RIGHT! I’m gonna tell him to meet you at his favorite restaurant.”

“Correct!” Jon said, arching his back to get some momentum. “Now then... GET TO IT!”

Using all his strength, Jon threw Derpy forward where she fell a few feet, thus earning him the right to cross “tossing a pony off the side of a cliff” off his bucket list.

“Weeeeeeeeee!” Derpy exclaimed before expanding her wings and launching herself skyward, then back down at an arch.

Jon watched as she dive bombed downwards to a segment of land just below the castle. Because of how high up he was on the mountain, he had to squint his eyes to see where she was heading.

He knew she’d come through for him but he’d have more faith in her if it wasn’t for the fact that she was heading in the wrong direction, with Ponyville being at least a mile away from where she had landed.

“Wow,” Jon sighed as he made his way back to the main road. “I hope her husband isn’t as... naive as she is.”