Dear Pen Pal,

I hope this letter finds you well. Maybe I shouldn’t have started like that. I heard ponies do that when writing letters. I’ve already thrown so many of these away, and I don’t want to waste any more of the office’s paper. I’m writing to you, whoever you are, because I’m trying something new. Recently, a new mare has come into town and I think I like her. I barely know her, though. I pretty much only know of her, but I want to try. That’s why I’m writing to you.

The truth is, I don’t have many friends. I don’t have time for them. I’m a mare who works at the Ponyville Express and have a daughter at home. She’s my pride and joy, but between work and her, I don’t have much time for me anymore. Maybe I’ll tell you about her sometime if you want to know, but I want to be a little selfish right now if that’s okay. My little muffin top deserves the world, but I want to have a little piece for myself sometimes. I think that’s okay, right?

About this mare. She’s a unicorn from Canterlot and really out of my league. Like, she’s become a little bit of a local hero and ponies just seem to get pulled towards her. Maybe I’m being pulled in too, but it’s more than that. Even though she’s popular, she’s also a shut-in kind of like me. I think she likes books more than ponies. I get that. Ponies can be mean if you’re different. I’m not really that smart and get made fun of because I’m clumsy. I like to think I’m good at what I do though. Maybe that will be enough. This mare is really, really smart. Opposites attract, right? I heard that once.

I think that’s enough for now. I’ll put a stamp on this and pick a random address to send this to. I don’t know if this is against the rules or not. Please don’t be mad. If you don’t want this, just send it back and I’ll try again.

Sincerely,
Your New Pen Pal

Hi New Best Friend!

I guess we are doing a little bit of secret stuff since you didn’t tell me much. I don’t know where Ponyville is, but I’m in Equestria too! Maybe we could meet up if it’s not too late. I always like making new friends, and I know how lonely being lonely can be. Trust me.

And don’t worry about me being angry. I love surprise letters. It’s not the first one, but that one kind of dropped on me from the sky. Being a mailmare sounds very cool though! I don’t know many of those since we don’t send a lot of mail unless it’s something big. I should ask my friends about mailing more letters. Speaking of which, I’d love to be your pen pal! You can check the top if you missed it, new best friend!

As far as your love problem is concerned, she sounds like a cutie. Just go for it! The worst she can say is no, right? Besides, I know you sound all scared and insecure, but I can already tell that you’re just the most loveable pony. If you weren’t, how could you have a filly of your own? And little muffin top? That’s an adorable nickname! I love muffins too. So take all that muffin-y goodness and go get your mare, mare!

Lots of love from your new best friend forever,
Your Bestest, Mysteriest, Pen Paliest Gal Pal

Dear Pen Pal,

I finally worked up the courage to talk to her again. Really talk to her instead of hellos and stuff. You remember how I gave up for a long time after that shipping accident got dropped on her head? It was bad. I don’t want to think about it. But when I went there to her house, I was too shocked to say anything.

When I got there, she had just gotten done with a really big spell or something because she had wings like me! She was a unicorn before, but now she’s an alicorn! I don’t even know how that works. She must’ve just been so smart and wonderful that she got them. Everypony was so excited. I was too. So much so that I couldn’t talk to her.

I’m sorry. I know I said I’d finally be brave, but how am I supposed to talk to her now? I think she’s going to become a princess. But me? I’m just a klutzy mailmare with bad eyes. Maybe before I might’ve stood a chance, but after something so amazing happened? I can see it now. I walk up to her with a bouquet in my mouth doing my best to ask her out only for her to look at me with uneasiness and pity. I don’t think she’d be rude about it, but I’d be rejected immediately.

Pen Pal, I don’t know what to do. Should I try anyway? I couldn’t take being rejected. Please let me know what you think.

Thank you in advance,
Your Pen Pal

Cheer up Bestest Pen Gal Pal!

Neigh way! You too? My best friend turned into one of those. It was all glowy and rainbow-y! She’s the one I met through a balloon message before. She was my only friend for the longest time, and when I finally got to meet her, she was even better than I imagined! And even when she became an alicorn, she didn’t change at all though on the inside. That’s what matters.

Alicorns aren’t unreachable, unless they’re up in the air and you don’t have wings. You might need a helicopter then. But really, they’re ponies just like you and me, and they want friends just like we all do. I said it before in the first few letters you wrote, but you should totally tell her how you feel. And being a klutz? Psshaw! I think that’s how you write that. Yeah! Psshaw and pbbt! Just because you drop something on somepony’s head doesn’t mean it’s completely broken. You just have to put it back together and make something new! Even ponies when they break things on themselves can heal. I think you need to pick up that heart of yours and give it to her. If she gives you a chance, she’ll find out just how sweet and special you are.

You got this!
Your Supportive Bestest Pen Pal Around

Dear Pen Pal,

I feel like a stalker. I just keep watching Princess Twilight whenever she comes back to town. She’s so beautiful and she keeps getting more every year. The Princess of Friendship is a magnificent mare who everypony is friends with. Maybe that’s why she’s getting taller every time I see her. Dinky said her magic power comes from friendship, so the more friends, the more magic. She’s also managing the days since Celestia and Luna retired. She’s just everything I’m not.

I’m jealous. More than that, I’m angry at myself. I’ve wasted so much time being a coward and now Twilight is actually out of reach. I’d have to fly up just to kiss her. I dream of doing that sometimes, like how I used to dream that she’d tutor Dinky since I couldn’t keep up with her studies. It worked out in the end. My little muffin top went to both Canterlot’s School for Gifted Unicorns and the School of Friendship before recently becoming one of Twilight’s personal students. She’ll spend more time with her than I ever will at this rate.

Pen Pal, I’m scared. I’m getting older and Twilight is getting further and further away. Age doesn’t matter for her anymore now that she’s an alicorn. I feel like by the time I work up the courage to talk to her, I’ll be a withered, old mare giving a box of chocolates to an immortal goddess. Please, if you have any words of encouragement, I could really use them. Before it’s too late. I hope it’s not too late now.

Waiting for your reply,
Ditzy Doo

Dear Ditzy Doo,

I’ve read so many of your letters. I just want you to know that no matter how things go, you’re a good pony. I can’t imagine what you’re going through right now, but it’ll be alright. You are beautiful just as you are. If you don’t think so, just read all the letters I’ve written back to you. I don’t know how I’m going to get them to you, but we’ve got magic again, so maybe there’s a spell.

Speaking of, Dinky sounds so awesome! Just this morning I was reading about how adorable of a little filly she was, and now she’s all grown up? And she did all those things that I don’t have a clue about? You’re always telling me why Twilight is so lovely to you that it makes me forget sometimes that she’s also an important pony. By the way, those schools sound absotively sparkly!

Even if you haven’t worked up the courage to ask her out doesn’t mean it’s too late. If you don’t feel like your best self, then you’ve come to the right friend! My other best friend Pipp can make you look like your best self and I can unicycle something fantastic that will turn all of the heads. I’m almost certain it will be in a good way! So, please. Don’t be so hard on yourself. You are a lot. Missed opportunities don’t mean others won’t come your way. And who knows? Maybe the next one will be perfect! Even better than what you thought possible. If we ever meet, I will give you the biggest hug because I love all of my friends, and that means I love you a whole lot, too. You’re very loveable, so don’t be hard on yourself. Please.

Your bestest and caring friend,
Izzy Moonbow

Dear Pen Pal,

Dinky found the letters. We were packing up to go somewhere safe and then found my box. After reading a few, she really got onto me for keeping everything to myself. I thought it was good to let my emotions out, but she thinks I’ve been torturing myself for all these years since I was too scared to send them to you. So many unsent letters sitting in my little box in the attic, pining away for a princess who has vowed to never marry anypony now.

It’s sad. It wasn’t even her fault. For some reason, ponies are at each other’s throats and she doesn’t want to show favoritism towards any kind of creature. Maybe you wouldn’t like me now too if you weren’t a pegasus. There is so much hatred just bubbling up now for some reason, and I’m worried for my little muffin top. What kind of world is she going to live in if we all start hating each other because I don’t even know why? Some unicorns are already making fun of her for having a featherhead like me for a mom. She defends me, but deep down, we both know she must’ve inherited her smarts from whoever her father is. None of that big brain of hers came from me. She has to rephrase everything just so I can understand what she says, and it can take a while before it’s dumb enough for me. I know she isn’t talking down to me on purpose, it just happens. The princess would probably have to do that all the time if I’d ever ended up with her. I’m just so stupid.

And this was stupid. Here I am, writing this letter that I know I’ll never send because I’m too scared of your judgment and rejection, Pen Pal. I’m sorry that I didn’t trust you. This is my final letter to you. I don’t know if it was good or bad that I wrote so many of these. I like to think it was cathartic. That’s one of Dinky’s big words. She’s letting me write this last one while we’re packing. We’re leaving Ponyville and going to Canterlot, but we won’t be staying there. A lot of unicorns are really starting to hate pegasi and earth ponies there. Dinky says there’s a place we can go after that where our differences are erased and we can live peacefully again. She went on a field trip there once and said it was like a different world. Maybe that’s just what I need.

If I meet Princess Twilight while we’re passing through, I’ll do my best to confess to her just so I stop holding onto this hopeless feeling. Thank you again for everything, Pen Pal. Again, I’m sorry I never sent these to you. If you ever find these and can find me, I’d love to hear from you. Just ask around Canterlot for somepony named Sunset Shimmer. She’ll know where we are.

With love and harmony,
Ditzy Doo

Dear Ditzy Doo,

I’m sorry to have reached the end of this. I really enjoyed writing to you. And I know it’s scary for you right now, but I want you to know that everything will be okay in the end. Not going to lie though, it might be bad for a very, very long time. But the Equestria I know is a wonderful and magical place filled with friends everywhere you look. So, you don’t worry about that at all, okay?

I know for a fact you didn’t read through these letters before you wrote this one, because if you did, you’d realize how special you really are. You raised an incredible filly who takes after her mommy’s kindness all the way through. And you know what else? It’s really cool having smart ponies around you. I told you about Zipp before, and my earth pony sometimes, alicorn other times friend Sunny is really smart too! They’re both pretty, athletic, and big-brained. Two total packages! Misty is really smart about certain things and can learn stuff like there’s no tomorrow. And Hitch? He knows a whole lot about taking care of creatures. Then Pipp knows everything about bringing out the best in anypony. Super duper important!

It’s a little jinxie for me to say this, but to tell you the truth about me, I don’t feel like I’m the brightest crystal in Bridlewood. A lot of ponies thought I was weird growing up, too. Lots of ponies still do. I guess what I’m saying is that it’s okay if you think you’re a little stupid. I’m a little stupid, too. But you can bet that nopony can unicycle like I can, just like nopony can deliver mail with a smile like you do. That’s not nothing. Never think that’s not valuable. You can’t be a really stupid pony while being really good at a thing. That’s against the rules!

So you went through Canterlot, huh? We went there before too, but we didn’t find ponies. Just a lonely dragon-something named Discord. Next time I see him, I’ll ask about Sunset Shimmer. He’s been there for a long time, so he might know.

When you read these, I know they’ll make you smile. A bunch of your letters made me, even when they got sad. Wherever you wind up, I hope you have nothing but love and harmony there. You deserve it. Hoof to heart, we’re really the best of friends forever and ever, Ditzy Doo.

Love,
Izzy Moonbow

“I wonder if I should add a little heart,” Izzy pondered aloud to herself. She giggled to herself. “What am I saying? Of course I’m going to add a heart! Maybe a whole border of them!”

The bubbly unicorn doodled away with a hum on the last reply. She wanted to make it special. After all, Ditzy Doo had sent her so many. More letters than she’d ever received in her life. There might be even more if any were missing. The box was very old after all being in the mail so long. It’d taken a very long time for Izzy to get her hooves on it. It only seemed fair that she made sure to show her appreciation. Hearts, stars, horseshoes, balloons, she just let her imagination take the wheel all the way around. It was totally worth it. Ditzy Doo was totally worth it.

As she whiled away at the border, there was a light knocking on the door to her unicycling workshop, also known as the closet she’d commandeered in the brighthouse for a little privacy.

“Hey, Izzy. You still in there?” Zipp asked warily. “It’s been hours.”

“I know! My magic and hooves are absolutely wiped out. But, I’m just about done. I can almost taste it!”

“Taste? Okay that’s it! You better not be making your surprise closet cake after the last time!”

Zipp stormed through the door and was surprised to see the little, makeshift desk Izzy had thrown together. Her eyes immediately started scanning for illicit baked goods when a waft of something awful crossed her nose. She recoiled from the stench and backed off.

“Oh gosh. I think I’m gonna be sick.”

“I know right? I was wearing a mask at first, but I got used to the smell eventually.”

The pegasus covered her muzzle with her feathers. “It smells like a library made of rotting driftwood in here!”

“You’re almost right! But what you’re missing is the fungus that was growing on the side of the crate I bought at the night market!” Izzy spun the crate around to proudly show off the stinky shroom to her friend. “Super smelly right? It came with the letters.”

Zipp tilted her head, her curiosity winning out over her disgust. “Letters?”

“From Ditzy Doo, my pen pal.”

“Okay, first question. Who in Equestria would send letters in a crate like that? Second. How could she be your pen pal if you bought them at the night market?”

“They just came like this when I got them. And Ditzy Doo really needs a pen pal, so I’m writing her back.”

Zipp took a deep breath away from the closet and ventured in to see what the mare was on about. As she approached the desk, her jaw nearly dropped seeing the ancient letterhead pages sitting beside Izzy’s fresh paper. Zipp didn’t dare open her mouth, or else she might get too much of the musty air in it.

“Izzy? How old are these?”

“Really, really, really old. Some of them are from before Princess Twilight was a princess.”

“Seriously? How do you know that?”

“Because I read her letters! I actually just got done replying to the last one. See?” Izzy flashed the paper up to her friend to show off her excellent doodle-work. “I even drew all of us together. She was really worried about the ponies getting along, so I wanted to show her all my friends.”

Zipp took a long look at the letter, skimming over the content before her eyes drifted down to Izzy along with all of them in front of the brighthouse door. She turned back to her friend with a little apprehension. “But, if she’s from Twilight’s time, then you know she can’t be… she won’t be able to read these, Izzy.”

“I know. But Ditzy Doo needs a pen pal,” Izzy tapped her hooves together as she kept her smile on. “Just because they got a little lost on the way here doesn’t mean I shouldn’t reply to them. She’s lonely, Zipp. And scared. Everypony should have a friend, especially when they’re lonely and scared. Right?”

The pegasus looked at the letter then back at her friend with a soft smile. “Yeah, Izzy. And I can’t think of a better pony to have as my pen pal.”

Izzy bounced back with a wide smile. “Really?”

“Without a doubt. You always brighten up my day in your Izzy way.”

She took Izzy’s reply in hoof, admiring the little picture of all of them together. Izzy herself was waving with Misty smiling by her side. She’d drawn Zipp flying above Sunny, Hitch, and Sparky. Pipp was in the front since she was the pony taking the selfie with all of them. It might’ve just been a quick, crudely drawn picture of everypony, but Izzy had put all of her heart into showing Ditzy how happy they were together. Nopony could doubt the warmth of their friendship.

“You said her name’s Ditzy Doo, right?”

Izzy nodded enthusiastically. “And her daughter, Dinky Doo, too!”

“Can’t forget her,” Zipp noted with a giggle. “You know what’s better than a letter from one pen pal?”

Izzy tapped a hoof on her chin as a wry smile crossed her face. “Maybe a letter from two pen pals?”

“Try six.”

The unicorn gasped excitedly and coughed only a little from the slightly noxious fumes. “That’s hextuple-rrific!”

“Exactly. But maybe not every letter. It’d be cool if we all wrote at least one to her.”

“Yeah.” Izzy’s wide smile tired as she turned to the stacks of letters sitting in the deteriorating box. “To be honest, it was hard to read at times. I wish I could get a time machine and go back to give her a big hug.”

“If we had a time machine, I’m sure there’s a lot of things we could do. I know I’d want to ask Princess Twilight about this whole Opaline situation and how we can stop her.”

“I don’t think you’ll find anything like that in the letters, but I know you’d want to read them anyway, Miss Investigator Extraordinaire.” Izzy waggled her eyebrows.

Zipp looked away and scratched the back of her head. “Yeah, yeah, read me like a book. But seriously, I think I’d like to write back to Ditzy first.”

“But you said she’d never be able to read them.”

“Maybe. Maybe not. Like you said, that isn’t a reason to not write her back. Besides, it’s always good to make more friends.”

“Great! Then let’s get out of my hidey-writey closet so we can get to everypony replying!”

Zipp blinked at the name. “Were you cooped up in here just because you knew I’d want to dig into these for clues?”

Izzy froze and plastered on her best smile. “Maybe just a teensy, little bit?”

“Well, next time, maybe try finding a hidey-writey open field or something. Pipp’s gonna throw a fit when she finds out all of her favorite clothes smell like rotten mushrooms.”

“Don’t forget about the driftwood library musk!”

Zipp blanched and shuddered. “I wish I could.”

Izzy magicked the crate onto her back, carefully resting it on her back so it and the years-worth of letters wouldn’t break down any more than they already had. It was nothing less than a miracle that they’d held together so long in the first place. Zipp helped out by grabbing Izzy’s stack of replies and carrying it for her. As the two friends trotted together, Zipp took another look at Izzy’s last letter and smiled tenderly.

“You’re really amazing, you know that, Izzy?”

“Aww, shucks. You’re going to make me blush, Zipp! You’re not too bad yourself,” she added with a silly wink.

“No, Izzy, I mean it.” She put a wing on Izzy’s shoulder. “And I know Ditzy will be so excited when she gets these.”

The happiness Izzy was wearing slipped off, replaced by a bittersweet melancholy. Feeling the wing shift around her neck into a supportive hug, she sucked in her lips and nodded, doing her best to play along despite what they both knew deep down.

“Yeah. I can’t wait to hear back.”

Author's Note

This story is dedicated to the ever important "Audience of One". The one whose life may be made better with a momentary escape from reality. Whoever that one happens to be, I hope you enjoy this story. I will do my best to tell it. - Lord Regulus

If you find a simple mistake in the GSP (Grammar, Spelling, or Punctuation), please let me know through a private message rather than leaving it in the comment section.