The New Babysitter

by Junglehero

Chapter 1: The Beginning

In a seemingly normal house in the middle of suburbia, (which actually was anything but) a small, blond child walked down the steps of his home. Wearing his striped pajamas and dragging his stuffed Tiger behind him, he walked up to a dinner table where his babysitter, an equally blond teenaged girl, was attempting to work on a school project.

"Rosalyn," he asked the teen, trying to sound as cute as possible. "Could you please check outside? I think I saw a monster out there."

"Calvin," Rosalyn said reassuringly, turning around. "There are no monsters out there. It was probably just a raccoon or something. Go back to sleep."

"Could you PLEEEAAAASEEEEE check? Just in case?" He made his eyes look so big and adorable Bambi would be proud.

"Oh, ok, if it'll make you feel better," The babysitter replied. She walked to the nearby back door and stepped outside, looking around into the darkness before her. All she could see was the vague outlining of various trees.

"Calvin, I don't see any..." Suddenly, She heard the door slam behind her, followed by a faint clicking sound. Rosalyn rushed to the handle and twisted it. Her suspicions were confirmed, it had been locked from the inside.

“CALVIN!!! You let me back in the house this INSTANT!!!"

"Don't worry Roz," The boy said through a closed window. "There's only 50% chance of rain tonight! Ha ha!"

"YOU'RE INSANE!!!"

Calvin laughed and left the window to go enjoy the spoils of victory. Rosalyn shouted out more threats and a few obscenities at him, but he wasn't listening. He was too busy savoring the moment. This child wasn't new to mischief, in fact it was his favorite past time. However, his rivalry with his babysitter was something special. They antagonized each other from the very beginning. She would scold him, ruin his fun and send him to bed nearly two hours early. He in turn did everything in his power to spite her. He stole her study material, said bad things about her to her boyfriend, and even called the cops on her one time!
But even with all that under his belt, he viewed this most recent event as his greatest triumph! With Rosalyn locked out of the house he could watch TV and eat cookies all night with his best friend, Hobbes the tiger, and boy was it fun! Even though the plot was eventually foiled by the return of Calvin’s parents later that night, and although he did feel bad while was being punished, Calvin grew to be extremely proud of his latest victory against his eternal adversary.

Unbeknownst to him, it would be the last time he ever saw Rosalyn ever again.

---

High leadership roles are always deceptive. You believe you'll be out doing things, making all the important decisions, really making a difference. Then when you get the position, you realize all it amounts to is doing a ton of paperwork. Royalty complains about this, presidents complain about this, and even principals such as Celestia complain about this. This thought just entered her mind as she was finishing the last contract that would finally cover up what was becoming popularly known as the "Equestrian Incident." When she got this job she thought she would make a big impact in young people’s lives, and in many respects she does. But she soon learned not only did this job require spending more time in a office then she would have preferred, but just the very word "principal" creates a bad taste in young people’s mouths. It’s like how most Queens in fiction take after the evil one from Snow White, the title simply implies nastiness. Celestia was able to subvert this trend and gain the adoration of her students, but it just was another reminder that leadership isn't all it was cracked up to be.

She was about to start another sheet when her phone began ringing, saving her from her eternal boredom. She took her phone off of its stand and put it up to her ear.

"Hello? Principal Celestia of Canterlot High speaking. How may I help you?"

"Tia? Hi, its me!"

"Oh!" Celestia exclaimed, recognizing her friends voice. "Hey! How are you? I haven't heard from you in forever!"

"I've been good. Incredibly stressed out, but good. You?"

"The usual. School dance drama, paperwork, aliens from another dimension fighting giant orange demon people. Its been pretty good."

"Uh huh," the voice on the line said, hoping Celestia was being sarcastic. "Anyway, I would love to chat, but I desperately need your help!"

"Is Calvin giving you trouble again?"

"Actually that's what I wanted to talk you about."

"Oh." Celestia started to get nervous. "What is it?"

"Well, you know how Calvin can be a little..." She paused to pick a proper word that would be safe for work. "rambunctious, at times.

"Rambunctious? You told me that he somehow managed to flood the house. MULTIPLE TIMES!!!!”

"OK, you have a point. Because of his... energetic personality, we could only find one person in town that would babysit him. And three months ago she moved! She went off to college and now I can't find anyone to take care of him!"

"No one? Out of all the people in your town?"

"I've been looking for weeks, but it seems Calvin has grown quite the reputation around here. Anyone who I ask just ends up bawling on the ground laughing at the very idea."

"Its that bad huh?" Celestia asked.

"I'm afraid so." The woman lamented. "So I was wondering if you could help me out? I know my house is a little bit away from the school but..."

"I'd love to babysit him and all, but I don't know much about children his age. I work with mostly teenagers." While this was true, Celestia also made this excuse because the thought of her babysitting that child filled her with a amount of fear that she never thought a six year old would be able to give her.

"I thought you might say that," Calvin's mom has learned from her past experience and can now read potential babysitters like a open book, "but that's not what I meant. You know a lot of teenagers, it's literally your job, so I was wondering if you could find someone responsible and ask them if they want the job. There has got to be somebody in your school who's up to the challenge."

"Admit it, the reason you want someone from here is that no one here has heard of Calvin."

"You got me," Calvin's mom admitted.

Celestia sighed. "OK, I'll think of someone. But it might take some time."

"Please hurry" the woman begged, "I've had to spend 3 WHOLE MONTHS without going out. I honestly think its effecting my mental well-being."

"I'll do the best I can." The bell suddenly rang, echoing throughout the halls, signaling the end of school day.

"I gotta go." Celestia said quickly. "I'll call you back."

"Alright. See you later."

Celestia hung up, gathered a few essential items, and began to walk out of her office and to her car. On the way, she thought about which of her students would be the best fit for watching Calvin. Celestia makes it her duty to get to know her students personally, it makes the learning experience more tailored for each individual, so no research was necessary.

"Fluttershy works with animals a lot," She began, "so she has experience in this sort of thing. But she's too soft; she won't be able to take Calvins insanity. Applejack is both responsible and tough, but I doubt she'd want to add a job to her workload, considering she has to balance both her schoolwork and running her family's farm. Rainbow Dash? Ha ha no. Um, who else? Who else?"

She was in the front courtyard thinking when a sharp cry sliced through her thoughts. She looked around to locate the source and her eyes fell on a student named Derpy (Celestia was still unsure if that was a just a nickname or not. If not, her parents must be very cruel people.) However, the cry did not come from her, it originated from the baby that was in her arms, which actually looked a lot like her. Derpy was trying to calm the baby girl down but to no avail. She looked like she was about to panic when another student walked up to her.

This girl was completely pink: her hair, her clothes, even her skin, was all differents shades of that color. The only area of her not pink were her eyes, which were a light blue, and a design on her skirt made to look like a bunch of balloons. Her aforementioned hair was so poofy it strongly resembled cotton candy and she mostly skipped to get places instead of walking. It was none other than Canterlot High’s resident party planner, Pinkie Pie.

She said something to Derpy (Celestia couldn't hear her because of both the distance and the child's crying) then she turned her attention to the baby. Pinkie smiled at her then began making a plethora of silly faces, many of which would be impossible for a normal human being to accomplish. The baby almost immediately stopped crying and instead started to laugh, which was so much more endearing. Derpy thanked Pinkie and walked away to her car.

Celestia began to rack her brain for everything she knew about Pinkie. She ran nearly every party related committee on campus, so she knew she was responsible. Pinkie got decent grades and rarely got in trouble, and even when she did it was only for an harmless prank. (She rarely did anything actually malicious.) She was one of the six students that stood up to the demon Sunset, so she was brave. And the moment Celestia just witnessed was prove that Pinkie was good with kids. It was a perfect match!

"Pinkamena Pie!" Celestia called across the courtyard. "could you please come here?"Pinkie cringed at her name being called by the principal, which Celestia has gotten use to. "Don't worry you're not in trouble." When Pinkie heard that, she immediately lost all her anxiety and bounced over to where the principal was standing.

"Whats up?" Pinkie asked casually.

"Pinkie I have a question for you."

"OOOO! OOO!" She suddenly burst out, "I know this one! Um, 27. No wait, 1892! No wait, Pineapple!"

"Pinkie, this isn't a pop quiz. I was just wondering, you've worked with kids before right?"

"Yeah, of course!" Pinkie declared proudly. "As a ultimate party planner, I have been in charge of a TON of kids birthday parties, plus I regularly babysit Mr. and Mrs. Cakes twins."

"Perfect! Pinkie, would you be interested in another babysitting job soon? A friend of mine really needs a good babysitter for her child."

"Absolutely!" Pinkie replied, "I'd love to help out! I need some cash to buy more party supplies anyway.”

"Great!" Celestia gave Pinkie the number she needed to contact Calvin's mom, then the party planner began to bounce away. But Celestia felt like she had forgotten something.

"Oh wait! Pinkie!" Pinkie stopped and turned around. "I forgot to warn you, the kid you'll be babysitting, he's can be a bit... misbehaved at times. So be ready for anything.”

"Don't worry Principal Celestia!," Pinkie said "I've met a lot of different kids in my life. And if I can handle the Cakes twins, there's no kid I can't handle!"

‘She has obviously never met Calvin.’ Celestia thought.

Comments

[Flying Fantasy Horse]

awesomegifs.com/wp-content/uploads/Ron-Swanson-is-excited.gif

This is going into my favourites.

[Wacky]

Oh the potential this holds...

[Dragon Spire]

This can only end with the 4th wall being torn down, I know it . . .

[HB_DS2013]

Oh, this is the EGverse. Why do I forget that?

[TheMainManeMaineBrony]

This pleases me. Continue.

[Saltyoven]

Creative, and loads of potential.

[Synthetic Soul]

This is going to be good.

[The Nightmare has Come]

Ohmygosh! More?

[LtMajorDude]

Good story so far.

m.quickmeme.com/img/5c/5c3af071d5956eb1924f5730648158e70ea1ec1ff8995dbf11ad9d71d0637e4d.jpg

[SuperWeegeeWorld]

Calvin and Hobbes getting a replacement babysitter in the form of a human version of Pinkie Pie. That is a disaster just waiting to happen. And, to be honest, I don't have any idea which side, if either, I should be feeling sorry for. At any rate, I'll wait and see what the future holds in regards to this story.

[Toobert]

The only way I can see a more chaotic crossover pairing for babysiter and child is if Dan was babysitting Calvin. This, I am unashamed to say, is going to be positively Chaotic.

[Warrior of Stone]

*Sees title, cover photo, and description*

I LOVE YOU WITH MY ENTIRE BEING.

[ArcIsDead]

4743246 WHAT HE SAID!!!

[butterfield pancake]

4742631 either that or Pinkie's pranks put Calvin to shame

[The Cardboard Box]

Nice to see this getting regular updates.

OH WAIT.

[Junglehero]

4863605 I'm almost done with the next couple of chapters.

[Lady Maria]

MOOOAARRRR!!!!!!!

[Warrior of Stone]

4864906
Wait, next COUPLE?!?!
*Literal scincere applause*
THAT EXPLAINS THIS, now im 100% ok with this taking a while.
Im being very honest right now, hard to tell but I am.
Keep on rolling

[Chaos da FaceWhacker]

Since when did having the actual,physical,living embodiment of random insanity,(also known as Pinkie.) babysit Calvin and Hobbes a good idea?I LOVE IT.