• Published 12th Jun 2012
  • 2,976 Views, 70 Comments

The Mailmare And I - MaxBeezy



A Writer travels to Ponyville, and starts an unlikely relationship with Derpy Hooves.

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First Date

The morning came, and the clouds dissipated. The storm that had plagued the night had passed. I awoke to find myself in the same position I was in when I slept; on my back, and Derpy still gripping my body. I gently caressed her face, waking her up. She slowly opened her eyes, and looked up to me, smiling.

“Good morning.” she said to me, “Did you sleep okay?”

“I slept just fine.” I replied, “Yourself?”

She yawned, but her smile never left.

“Very well, thank you.” She rested her head on my chest, like she did before.

“How about I make some breakfast?” I asked her.

She loosened her grip of me, resting a hoof on my chest.

“Are you sure? I don’t have much.”

“I’ll manage.”

Looking through her kitchen, I found everything that I needed to make a good breakfast. There were eggs, flower, various fruits, and my birthday muffin, which hadn’t been touched since the single bite I took of it last night. It luckily survived the storm. Interestingly enough, the kitchen was one of the few places that didn’t have leaks in the ceiling. “Not much” she said? What I saw was a feast.

In what amounted to mere minutes, I made a plate of scrambled eggs, cut up some strawberries, and split my muffin into two, with the bitten side given to myself, of course.

Derpy walked into the kitchen as I set up the table, wrapped in a blanket, avoiding any water filled pots on the way in. Her eyes widened at the food that I prepared.

“Wow!” she gasped, “You did all this?”

“I may not be a five star chef, but I can make a mean scrambled egg breakfast.”

She giggled that wonderful giggle as she sat down.

As we ate, I made occasional glances at her taking a bite of the eggs. She reveled in every bite; I was glad. At first, I thought she was being nice, but then I saw her looking at my egg plate, with that familiar look of somepony wanting more. I gladly gave her what was left. The fruit and muffin half more than made up for it.

Derpy wanted to clean the dishes, but I would have none of it. She spent the last couple months doing things for me, keeping me company, and making me feel wanted, that it was now my turn to do things for her.

I was finishing cleaning up, when I turned to see her still at the table. Her face in deep thought.

“What’s wrong?” I asked, “Are you feeling okay?”

“I’m fine. It’s just….” she paused.

“It’s just what?”

Her silence was palpable, like she was trying to form her thoughts.

“Now that we…kissed, and slept together, and you made me breakfast, does that mean we’re…” she paused one more time before delivering the final word, “Together?”

“Of course!” I chuckled, “We wouldn’t have done all that if we weren’t going to be together.”

“Does that mean we’re dating too?” she asked enthusiastically, with a wide smile.

“Exactly!” I replied, attempting to mimic the same amount of enthusiasm. As enthusiastic as I was, I could never match her.

Suddenly, she went silent again, looking very confused.

“So…” she trails off, “What do ponies do on dates?”

Before I could say a word, I went silent as well. The confusion she had on her face made its way onto mine.

“I…have no idea. I’ve never dated before, to be honest.”

“I guess that means we’ll find out together, right?” she smiled; undeterred by my admission.

“Right!” I said, putting my hoof down on the table. She found my determination rather amusing.


We walked into town, spending most of the day watching other ponies; ones that were in relationships, or what looked like relationships. You might call it voyeurism, we called it research. We found a couple subjects in town to watch, but none more so than in the more common hang out place for dating ponies; the park. There, we saw others having picnics, cuddling, nuzzling their noses together like they were Eskiponies.

Picnics in the park, we could do, but that bit with the noses looked rather strange to us. Giving it a try, Derpy and I nuzzled our noses together, doing our best to mimic our subjects.

"This is very strange." she said.

"Yeah, I'm not sure what the big deal is."

"Actually, this kind of tickles!" she chuckles.

I could feel a sneeze coming on any second, so I pulled away out of fear that Derpy would be blasted by any possible snot. I was right, I sneezed a powerful one into my arm.

"Celestia bless you!" Derpy laughed.

In the end though, our most valuable finding was that this dating thing actually wasn’t all that different to when Derpy was giving me a tour of the town, albeit with fewer stops, and with more romantic intentions.

As we watched a couple, whilst hiding in the bushes, we came to a conclusion.

“I think I could get the hang of this.” I confidently told her.

“Me too. It doesn’t look too bad.”

“What doesn’t look too bad?” A deep southern voice said behind us.

Shocked, we stood up to look at the source of the voice. Behind us, was a big red stallion, with a halved apple for a cutie mark, staring at us with the mother of all stares. I had no idea what to do or say, but just then, Derpy called him by his name.

“Big Macintosh?!” she said, “What are you doing here?”

His name was Big Macintosh? The stallion certainly lived up to the name. He was tall, muscular, almost made me feel inferior to him.

“I could ask you the same thing, ya two snoopers. What are ya’ll doin’, spyin’ on a couple ponies?”

“Well…uh…you see…” was all I could say before…

“I’m sorry Big Mac…” Derpy interjected. “You see this here is my coltfriend and we’re not really knowledgeable on the subject of dating so we decided to spend the day walking around town to see what dating was actually like and now we have and think we’re ready unless you have some dating advice for us maybe?”

She said it so fast, that she didn't make any attempt to pause, or add commas to her massive run on sentence.

Big Macintosh was wide eyed, like a massive bombshell that just rocked his world was dropped.

“He’s…your coltfriend?” he quietly said.

He was quiet for a few moments. I didn’t know what he was thinking during that time. Suddenly, he grabbed us both, embracing us at the same time.

“Congratulations!” he happily yelled.

His grip was unbearably tight. I couldn’t breathe.

Big Mac…” I gasped for air. He let us go.

“I’m sorry. Don’t know my own strength sometimes.”

“It’s…” I wheezed. “…quite alright.”

Big Macintosh chuckled, but then his face got serious.

“Alright, now listen here, mister. Ya better treat her right, now. Ya hear?”

I quickly nodded. I had no intention of mistreating her, but I had to respond quickly, or risk getting on this stallion's bad side.

“Now here’s what ya do. Ya take her to a nice restaurant, preferably with candles and nice music, and get whatever she wants. It doesn’t matter how much it is, you get it! You’ll find plenty in Canterlot. Nod if ya understand me.”

I do so.

"Good. What are ya standin' around for? Get moving!"

“Big Mac, I didn’t know you were dating somepony. Who is it?” Derpy wondered.

Big Macintosh became shifty eyed before responding with an “Umm…” and then galloping away.

That was a strange encounter. Still, if that's was what I needed to do, I guess that was as good advice as any.


We had our first date that very night. I took her to a nice restaurant in Canterlot, just as Big Mac told me to. It was called the Fleur De Lis, owned by somepony named Fancypants. Being a restaurant in Canterlot, Derpy and I attempted to dress in less than casual wear. I put on my nicest tie, while she wore a simple white dress, which looked very good on her. Upon entering however, the place was still more than enough to make us feel a little out of place in. The ponies around us wore such fantastic suits and dresses; we thought we accidentally stumbled into the Grand Galloping Galla.

The pony that seated us wasn’t too pleased with our attire, but he led us to our table nonetheless. We could feel the eyes of others staring at us. I was about to stare at them back, but I fought myself not to. We were there to have a good time, and it was best not to spoil it.

I admit, the table was nice, and there actually were candles on it. I wondered if this was the exact place Big Macintosh was talking about.

“I think we’re a little underdressed.” she whispered to me after we were seated. “I’m amazed we were even allowed in.”

“I know. Next thing you know, Princess Celestia is going to walk in.” I whispered back to her, who responded with a quiet laugh.

“I feel like everypony is staring at us.” she looked around to confirm her suspicions.

I placed my hoof on hers, drawing her attention back to me.

“Let them stare.” I said, “Then, they can see how beautiful you are.”

She lightly slapped my hoof away, laughing as she did it.

“Stop it, you.” she coyly said.

The Waiter showed up in a matter of moments, unaware of our little conversation. He was polite, and nonjudgmental, something that we both hoped he would be. He treated us like any of the more debonair ponies in the restaurant. It was a nice contrast to the pony that seated us, and crowd that was still making occasional glances at us.

In all fairness, despite the price, the food was delicious. I would say it was worth every bit, but I was certain the bill would take out more than half of the bits in my pouch.

Halfway through our meal, a white stallion, with a moustache and a monocle in his eye, stopped at our table.

“Good evening.” he said, with all the grace a fancy pony such as himself would say, “How are you two? I trust the food is to your liking?”

“It’s fantastic.” I replied.

“Very good. I was passing through, and I couldn’t help but notice that others were giving brief looks at you two. I say, are you ponies famous, or something?”

Both Derpy and I blushed. I wished that was the reason they were staring at us, but from their looks, that definitely wasn't the case.

“As wonderful as that would be..." I replied to him, "I think it might be because we’re from Ponyville.”

The name of the town brought a smile to the stallion's face. This wasn't the first time he's heard of Ponyville.

“Ponyville?!” he said with glee, “It’s so nice to see ponies from that town. Just last week, a red stallion came by with a lovely earth pony who was a teacher at the school there. What was her name?”

As he mumbled the possible names of the mysterious mare that accompanied Big Mac, Derpy quietly said…

“I’m sorry, Mister.”

He was broken from his thoughts to look at Derpy. His kind and gentle expression showed that he was never once bothered by her eye. A welcome sight, indeed.

“My darling, for what?”

“That we’re a bit…not fancy looking.”

“It’s perfectly fine, dear." he chuckled, "It’s rather refreshing, if I do say so myself. In fact, it’s nice that you’re wearing something simple, rather than some of the monstrosities I’ve seen. You look positively radiant!” he turned to me, “Young Colt, doesn’t she look radiant?”

I didn’t need a second thought to answer that question.

“Every day.” I said.

“Ah, young love. It’s very rare to see nowadays. Well, continue your meal, before I overstay my welcome.”

“It was nice to meet you Mister…?” I paused, waiting for the name.

“It’s Fancypants. And likewise, young colt.” he said as he walked away.

Derpy and I looked at each other, wide eyed in surprise and shock. That was THE Fancypants, talking to us!

The moment of elation didn’t last, once the bill came in. As great as the food was, the price almost made me have a heart attack. Still, I had enough to pay for it.

Derpy offered to chip in, but like the dishes at her house, I wouldn’t let her.

“You paid for my first muffin.” I said, “It’s my turn.”

“That muffin didn’t cost 50 bits.” she replied back.

“True. I hate to see how much dessert would cost.”

We didn’t want to find out. After paying the bill, along with a nice tip for the Waiter, we headed out the door, and back to Ponyville, where the food was cheaper, especially dessert.


You’re probably thinking that we made a stop at Sugar Cube Corner, but we didn't get back to Ponyville around the ten o' clock hour, and they closed at nine. Instead, we stopped at a stand of delicious looking apple treats, commandeered by a particularly energetic cowpony.

“Howdy!” she said with a manic energy, despite the late night, “What’ll it be?”

She had the same southern drawl as Big Macintosh, and an apple related cutie mark. Could they be related? I wanted to ask, but decided not to, for one reason or another.

“Hi, Applejack!” said Derpy, “What do you have?”

Applejack was more than happy to run down the list of goodies in the stand.

“Well, I’m glad you asked, Derpy! We got apple fritters, apple pie, apple tarts, apple dumplins, apple crisps, apple tumblers, apple cupcakes, apple muffins, or if ya like, just plain ol’ apples.”

We were both sure that we missed half the things she said, and that was all I can remember.

We ended up getting an apple pie. As Applejack packed it up, she glanced up at me, then back at Derpy.

“Ya know, I gotta ask. Who is yer new friend?”

Derpy giggles. “Oh, he’s not my friend…he’s my coltfriend!”

Coltfriend. It was the second time she called me that, but now, it was the word heard all around Ponyville. As amazing as it seems, everypony around us stopped. Even Applejack, who was almost through with packing up the apple pie.

“Come again?” she asked, after what was seconds of silence.

“He’s my coltfriend!” Derpy said happily, as she tossed a few bits on the stand, taking the boxed pie by its straps.

“Chhhhhank yooouuuuuu!” she muffled, as we headed off.

"I was going to pay for that." I told her.

"Nonthense! I gotch it!"

It was then, that we noticed the other ponies looking at us. The cat was officially out of the bag.

“Didch I thay thomething?”