• Published 5th Nov 2018
  • 3,082 Views, 156 Comments

Five Crazy Trials to Date Pinkie Pie - B_25

Spike endures five trials to understand what intimacy with a mare is really like.

  • ...

II - Two Hundred and Fifty Rules

~ II ~

Two-Hundred and Fifty Rules.

“Alright then, Spikey!” Pinkie's hoof slammed against the desk; I felt her eyes narrowing on me. “So you head about the challenge then, huuuuuh? Thought you of all my friends would go for my lips!” Her hoof raised to said lips, impressing on them. “How dare you! What have they ever done to you anyway?!”

“Nothing?” I slumped into the wooden chair, its armrests stabbing into my sides. “Sure, they kinda talk a lot, but I don't really mind that.” I scratched my throat. “Actually, I kinda like that. Because you talk a lot, then I get to talk a lot, and then we always have something to talk about, y'know?”

Why the heck was I talking so weird? Fake words poured from my mouth again, and like always, I was helpless to stop them. They just came and went, standing on their own, hoping to make sense or, at the very least, trying to fool those who heard them—me especially.

The strange thing was, even though my words felt like lies, they weren't. What I had spoken were my feelings, despite how vague and unfinished that they were, so much so, that they just felt like lies instead of incomplete thoughts.

Crud. Overthinking again. I had to stop that.

“If that isn't just the sweetest thing on icing cake!” Pinkie's stern expression shifted to closed eyes and a wide smile. “I like talking to you too, Spike!” Her eyes reopened, and her mouth slipped a heavy breath out. “But we should probably start talking about dating. Like how you're going to date me, and how I'm going to date you!”

“So it's true?” I arched an eyebrow. “You'll date anyone who asks?”

“Careful there, Spike, it's not that easy.” Pinkie rolled her blue eyes. “I just think if someone is willing to give me a chance, then it's only fair that I show them the same kindness in return!” She stepped to the right, stopped at a filing cabinet, pulled out a long drawer. “No pony or griffon or even dragon has won the challenge before! But we always do end up learning something, or something about something.”

“F-Fair enough.” I sat silently, watching her hooves flicked through upstanding papers. What the heck was I getting myself into here? This was new and different, which was Big Mac wanted from me, but I never expected things to get so... weird. “So, uh, what's the closest someone's come to winning this?”

Pinkie glared at me from over her shoulder.

“Winning your heart, I-I mean.”

She looked down at the papers. “It's hard to say. I've had a lot of stallions that were very excited at the beginning, but when we got to the first trial, they kinda flunked out.” Her hooves lifted a stack of paper to the air. She then turned around, closing the drawer with a smack of her rump. “But we had fun while it lasted!”

“Wha... what's the first trial?”

“Oh silly, it changes!” Pinkie dropped the stack on the desk, which created a thud. “They always depend on how I'm feeling and who I'm with.” She took the chair on the opposite side of the desk. “I can't have you boys giving each other hints! That's just cheating and totally unfair to me.” She leaned slightly over the desk, closing one of her eyes and widening the other. “You don't plan on cheating now, do you?”

“Cheating on you or the rules?”


I glanced down for a moment. I didn't actually plan on going out with Pinkie Pie full-time—just enough to shake up my life and grant me some experience. Rarity was the goal, the reason for all of this, and I wasn't about to give her up for some games.

But I needed to win those games to win Rarity herself.

“I promise not to cheat,” I said, lifting my claw. “You have my word!”

“Good enough for me!” Pinkie smiled. She then dug her muzzle into her mane, plucking out a quill between her teeth, bringing and dropping it over the papers. “That's rule one and two agreed to then and there! I love then and there—they're always at the same place and time!”

“Same here I guess?” I shook my head and picked up the quill. I glanced at the contract, squinting at the small letters. “So I just check mark in the boxes and sign at the bottom of every page?”

“You got it!' Pinkie cheered. “Now that you've agreed to the challenge, I need to hear you say that you agreed to the challenge.” She scooted her chair forward. “Or else I don't know that you agreed to the challenge.”

“But I already agreed.”

“But you need to say it.”


“Because I need to hear you agree to the challenge.”

“I agree to the challenge.”

“I also agree to the challenge!”

“So we both agree to the challenge?”

“We both agree to the challenge!”

Pinkie pulled out another quill from her mane, crossing an 'X' over my check-mark on the first box. I glared at her pink face; she only smiled back.

“The heck was that for?”

“I'm agreeing to the contract too, silly.” Pinkie lifted an eyebrow. “Wouldn't be fair if only you were held up to the rules.”

“But you crossed out my check-mark!”

“Only because I agreed to you agreeing to it.”

“But you crossed it! Doesn't thatcancel it?”

“I already know that you agreed to the rule,” Pinkie said. “We don't need a piece of paper to know that as well.”

“I... guess that's okay then?”

“Great! You're already a step ahead most of the stallions.”

“Wait,” I replied. “Am I in competition with everyone who was ever your ex?”

“That's up to you, silly.'

I blinked, remembering this was Pinkie, remembering this was Mac's idea, and how I would not remember drinking all the shots he would be owing me when all this was done and over. Just think of the drinks, Spike, and you won't have to think about anything else afterward.

“Let's go over the rules then.”

“Rule one! Don't cheat on me.” Pinkie lowered her quill to the second box. “Rule two! Don't cheat on my rules.” She crossed that box. “Rule three! You can end our relationship only by sending me a letter in the mail.”

I checked, and she crossed.

“Rule four! You can let no one else date me while I'm, dating you.”

Checked; crossed.

“Rule five! You have to marry me if you win the challenge.”

I stopped checking. “What?”

“Kidding,” Pinkie replied. “You can't come to my wedding if this doesn't work out.”

“Can I be the exception to the rule?” I replied. “Twilight will smack me with a book if I don't show up.” I threw up my claws. “You and I were friends long before this challenge anyways. Wouldn't want... something like this to screw everything up, you know?”

Pinkie squinted. “Hmm. Okay!”

I sighed relief.

“Since you're a special one, we'll make this a special case.” Pinkie crossed out the entire section. “But no more special treatment, Mr. Special. Ya got that!”

“Relax Pinkie!” I replied. “The only more special you're going to get outta of me is my intelligence level, I swear! For however many rules you've got left, I agree to them all!” I glanced back down at the thick stack. “Just how many rules are there anyways?”

Pinkie pouted, crossed her forelegs, and looked elsewhere. “About two hundred and fifty.”

I sighed.

“This is the worst terms and agreements I've seen in my life.”

“I outta beat the crud out of you for that.”

Big Mac lifted his mug. “Was it really all that bad?”

“We talked about rules for four hours!” I lifted my mug, purging the memory with the assistance of booze. “I didn't know dating could have so many... so many complication and stuff! I tell you, most of that crud was probably made up.”

“Ain't all rules made up?”

“You get what I mean.” I slammed the mug onto the counter, turning to face the hazy red thing again. “Those were just silly rules she invented just to be... silly! That's nothing like true romance when you... where you... how you romance a girl!”

“Have ya ever romanced a girl before?”

“Well, no.”

“So how would ya know?”

“Because I've fantasized about it endlessly! You see this head here?” I tapped a digit against my forehead. “Inside here, dating isn't an issue! Rarity and I have gone on countless ones. I'm the perfect prince with the perfect words, and she's the perfect mare with the perfect dress that's not going to be perfect for long.”

Big Mac stared at me for a very long time. “...ya ever get off ta yer own ideas?”

“Shove off.” I turned back, crossing my arms over the counter. “I just imagine how things would go if the world were perfect. Always a nice evening at a restaurant, a pleasant conversation I'm always able to follow, where nothing ever goes wrong for the rest of the night.”

“That ain't how romances go.”

“That's how they should go.”

I felt like a child. “At least, it feels like how they should go. Let me tell you, I may never have been on a date before, but I can guarantee they're not enforced by a bunch of dumb, invisible rules.” I shook my head. “We just do what we want, talk how we pleased, and if that doesn't work, then it wasn't bound to work out in the first place.”

“Ain't that just the truth,” Mac's voice floated to the right of me. “Just a shame it ain't true for you. Why, I don't think I ever heard you swear around Lady Rarity.” He snickered. “Or ever gotten into a fight near her. Why, I reckon you wore a suit of all things just to not knock on her door.”

I wanted to throw a fist, but instead, sunk into my arms. “Fine. You got me.”

“Truth of that matter is that everypony changes for one reason or another.” Big Mac shifted in his stool, which squeaked from his weight—the fat red stallion. “We don't always mean to, and we don't always know what those reasons mean. But I reckon we still change anyway—if only ta learn somthin' new about ourselves.”

I glanced up at him from below my wrist. “I thought you went on dates to learn about somepony else.”

Big Mac shook his head. “Ya end up finding just as much out about yerself. It's reason why ponies do it so much.” He chuckled a sad laugh. “Probably the reason why ponies do it so much. It's there one of the biggest challenges ya could ever face up to live.” He smirked at me, or at least, I thought he did. “Including all them villains and problems Y'all faced in the past.”

I sat up at the mention of that. “You mean the challenges the girls faced in the past.”

He blinked. “But ya were always there.”

“Hiding and complaining.”

“How about that one time you went and saved the whole Crystal Empire?” Big Mac put a hoof on my shoulder. “They made ya a statue and everything! That's gotta count fer something or other, no?”

“Because falling to my death is the heroics they talk about in picture books.” My chest clamped, and my heart hurt—I lifted my mug and chugged, drinking the bitterness, letting it taint my tongue. “Aaaack! Oh, all that stuff was just crud I lived off.”

“Boy, ain't you sour!” Big Mac pulled back his hoof, using it lift his mug as well. “Just take the compliment! I swear, you better not be this way around Pinkie.” He went to drink, the mug touching his lips, though he pulled it away. “C'mon, Spike, ya have a marefriend now! Yer first one too!”

“Not a real one.”

“Just take the victory when ya can.” Big Mac threw back the drink, draining it in a few gulps. “Hnnngh. Now, ya have a marefriend, now yer one step ahead from where you were yesterday. Ya may not think it was a step in a good direction, but that's only because you don't have the slightest clue on where ya headin'.”

“So the best idea is just to wander?” I replied in a mocking tone. “Getting in the ways of ponies as I do so. Maybe hurting them?”

“The only way ya gonna find where you wanna go is to go lookin for it,” Big Mac said, “and you ain't gonna see too much from yer bedroom window. Ya gotta do an action to get a reaction... I think? Weren't it Twilight always saying that?”

“I wouldn't take advice from Twilight,” I replied. Behind me, balls from the pool table clacked together. The smell of smoke wafted into the air. “She blew hot air your way, and besides, it's not like she's getting out much either.”

“And that's a shame,” Mac said, “but that ain't a reason fer you to be dissin' family. Or holdin' yerself back for that matter.”

I looked back over my shoulder. At the pool table, four ponies gathered around it. Some had cigars in their mouths. Others had mugs in their hooves. They were all talking, all laughing, like the friends they were, ponies with... actual lives.

“Guess I should stop focusing on the failures of others so much,” I said as I faced forward again. “So Pinkie Pie then? You reckon it's worthwhile putting up with her and her crazy rules?”

“Those rules may not be as crazy as ya think they are.” Big Mac chuckled as he lifted his hoof, signaling to the bartender for another drink. “I never once told ya them mares were not crazy. No. Every mare is crazy in her own right. Question always seems to be if yer willing to put up with their craziness.”

I shook my head. “Feels like there's a bit more to it than that.”

“Then ya better go find out then.”

We sat together for a while. We didn't say much after that. We drank. We ordered more drinks when we had finished drinking. For the moment, we drank, and we thought, something that was better left done alone. For some reason, though, we never ended up doing those two things alone. We never talked, sometimes getting up to move, but it was always comforting to know, that no matter where your thoughts may go, your best friend was sitting next to you, entangled in his troubles.

As it stood, I had a marefriend. Pinkie Pie was my marefriend. It was official—she made me sign and then she crossed out my signature. It felt unreal mostly because it was. Sure, we were dating, but we weren't really dating.

All of this was a game on a slightly more intimate level. Pinkie had some trials for me. They were meant to prove something, or at least, entertain her in some weird way. It'd seemed like a waste of time, but then again, my time wasn't worth much at the moment.

I doubted I would learn anything.

Big Mac thought otherwise.

I'd stumbled home drunk again.

I made it inside the castle without making a noise, which was strange, considering all the pans in the kitchen I knocked over. No one came, so no one heard, which meant the sound never happened, at least to my hungover mind.

After a journey through the hallways which always seemed to shift, I finally found my bedroom. I never locked it, because to be honest, I doubt I could unlock it whenever I got back home. Walking inside and closing the door, I sighed into the midnight, not bothering with the lights.

I stumbled over to my bed. There was a flask on my bandstand. Sometimes it had water; sometimes it had more booze. I always liked to surprise myself. Usually, by this state of mind, I couldn't tell the difference until tomorrow morning.

So took a big swig. The flask was empty. Putting it back on my stand, I tried to think of when I last drank from it—then I remembered that thinking hurt. Sighing, I let myself fall back into the bed, landing roughly in the middle of it.

Softness matched by warmth embraced me. I smiled as my bed felt different. Reaching around for a pillow to hug around my chest, my claws scrapped around until coming across something plushy. Smiling even wider, I brought the bundle of warmth against my chest, appreciating how it wrapped around my limbs—almost like a living thing.

“Aw, thanks, Spike!” My eyes shot open. “I love hugs too!”

I looked down to see that I had a mare in my bed.

“But you better let go of my quickly!” Pinkie said down from my belly, smiling up at me. “You don't wanna lose the first trial, do you!?”

“A-Ack!” I shot up straight and crawled until my back slammed against the wall. “P-Pinkie! What the heck are you doing here?”

“Dating you of course, silly poke.” Pinkie sat up on the bed, bringing her thighs together. “Today starts the first day of our relationship! Aren't you just excited? Huh? Well are ya, are ya?!”

“Will you get out of my room, mare?!” I closed my eyes and shook my head. “I'm drunk and hungover! Don't you have any decency to give me some privacy?”

“But... but I thought I was a cute mare?”

“You're...” I had to bite my tongue then and there—a place where Pinkie definitely did not want to be. I wanted to curse at her for being so moronic, for being so creepy and weird—how this was probably one of the reasons why most stallions failed to go further with her. “...right, and I'm wrong.”


“Eh, no.” I let myself slumped forward. “I just... I don't know! It feels kinda weird to have you in my room of all thing, y'know?” I looked around in the dimness of my room. “This place is meant for me and me alone. It's where I think and sleep and do... other stuff!”

“I guess I get what you mean.” Pinkie lowered her muzzle. “Would you... like to put this into the rules then?”

“I... no.” I crawled forward, coming just before her. “Look, I'm just a little weirded out about how everything is going.” I sighed, reaching for her hoof. “Just gonna take me a little to get used to it. But, if we can, I don't wanna start... whatever the heck this is with a bunch of rules.”

Pinkie looked up at me and stared into my eyes for a little while. For a moment, we were both silent, alone together in the dimness of my bedroom—right at the time where thoughts and feeling I'd rather repress would come running out. This area was my isolated form of torture, and it didn't feel right to have someone else here.


I shook my head again—the room was becoming blurry again. “Yeah?”

“Are you... are you serious about dating me?”

“I kinda am.” I pulled my claw back, leaving her hoof untouched. “I've never dated a mare before, Pinkie, and honestly, you were the only one who said yes.” I turned, letting myself lie down. “And as far as your craziness goes, I've never really seen you as a mare... per se.”

“Well, that's silly.”

“I know.” I gazed up at the ceiling, feeling my eyes lose their focus. “I'm filled with a bunch of silly thoughts and feelings.” My eyelids became heavy. “But I'm hoping being with you, even for a little bit, can make me a less silly.”

There was silence only for a moment.

“But I like your silly.”

“My silly isn't always likable.”

“Then I guess we'll just have to see about that!”

It was still crazy to think I had a mare sitting on my bed. A member of the opposite sex, just sitting there, looking over me as my eyes came to a close. If my mind weren't a haze, I'd have more to say, but for the moment, I enjoyed the feeling of being alone without being alone.

“And... if you're really serious about dating me, then maybe, maybe I can toss some of the rules.” I feel the bed bounce as she stood up. “But you have to get rid of some of your rules too!”

“I don't have any rules,” I replied, feeling my consciousness fade away. “Cute mares get away with whatever, remember?”

“Does that mean I get to watch you sleep again?”

“Don't pull out a knife and we have a deal.”

There were no more words after that, besides the sounds of me maybe snoring. It's hard to say how much longer I was awake, everything dark and silent. I couldn't feel her in the room anymore, but a part of me knew she was watching. It should have been creepy; I should have been scared.

But the last thing I felt was a smile before I drifted off into slumber.