Twilight and Pinkie's Awkward Date

by Pony-Berserker

First published

Pinkie and Twilight are not into mares but end up going on a date.

Twilight and Pinkie are not into mares. But much to Twilight's dismay, she is forced to go on a date with Pinkie. Can Twilight get out of this nightmare? Why does Pinkie seem to be happy about their date? Something is not right...

The Most Awkward Date

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“Cupcakes? Check! Punch? Check! Balloons? Check! A bottle for ‘Spin the bottle’? Check! Phew! That’s the last thing on the checklist,” said Pinkie Pie as she showed Twilight the agenda.

“You see, Pinkie? Twilight said, grinning. "A good checklist makes everything easier."

“I don’t get it, Twilight.” Pinkie was slightly confused. “Why do I need a checklist. I always know what I need to prepare for a party and I keep that in my head.”

“Um...” Twilight felt embarassed but she managed to make an awkward grin. “Yeah... Memorizing can sometimes work too until you forget something.”

“My parties usually need just several things, Twilight. How could I forget about them?” Pinkie inquired.

“You know,” Twilight said, taking the checklist and crumpling it up. “Checklists are usually used by well-organized ponies. You don’t need them.”

Pinkie frowned and stared at her friend for a while. “Do you say I’m not well-organized?” she asked.

“Um... No, no, no. I didn’t say that,” Twilight wished she could teleport out of Sugar Cube Corner. She thought for a while, facehoofed and then teleported out of the confectionery.

Pinkie folded her forelegs on her chest and groaned.


Twilight appeared just next to Sugar Cube Corner but she was out of Pinkie’s reach. She sighed and started to trot home. How many times more was she going to embarass herself in social activities. Apparently, advices from the book did not work well in reality. She read that a good friend should always be ready to give an adivce to smeone else. Either the book was wrong, or the advice was not good.

Twilight arrived at the library. She opened the door and...

“How long shall I wait!?” Pinkie shouted at her.

“Gaaah! How? When? What!?” Twilight was so startled that she flinched and fell on the ground.

“Twilight! You, you, you insulted me! I’m not that stupid. How could you do that!?” Pinkie was on the edge of crying. That confused Twilight as Pinkie was rather angry when she left her in Sugar Cube Corner. The unicorn had always suspected that her friend suffered from a bi-polar disorder she had read about in one book.

“Well, I’m sorry, Pinkie. I’d just thought I could help you,” Twilight felt awful. She looked away from Pinkie and took a deep breath.

“Oh, Twilight. You never learn, huh?” Pinkie was in normal mood again.

“Y’all not gonna believe!” Applejack shouted as she trotted up to her friends. “Big Mac asked Rarity out!”

“What!?” Twilight and Pinkie could not believe and were visibly shocked.

“Yep, he just went to her and did it! Rarity was so shocked she couldn’t say no!” Applejack said excitedly.

“Oh, that’s... great,” Pinkie let a small grin appear on her face but she quickly saddened.

“Well, that was unexpected,” Twilight said.

“Y’all don’t seem to be happy ‘bout that,” Applejack remarked.

Pinkie and Twilight instantly protested and assured her friend that they are happy for Big Mac. Applejack was not so sure about that but she finally shrugged and trotted away.

“You look concerned, Pinkie,” Twilight said. “Don’t tell me you had a crush on...”

“No, no, no, no ,no!” Pinkie suddenly brisked up. “Twilight, please. Me and Big Mac? I wouldn’t date him even if he was the last stallion in Equestria.”

“Well,” Twilight hesitated if she should continue but after a moment she added: “Maybe you like, you know, Rarity?”

Pinkie jumped as if something stung her. “Are you crazy Twilight!? I don’t swing that way!” she shouted at her friend.

“I’m sorry, I’m sorry! I should really stop talking!” Twilight blushed and nervously closed her eyes. She couldn’t look in Pinkie’s eyes. She was ashamed of her behaviour toward her friend this day.

“If you want to know, I’m just jealous,” Pinkie said. “Well, I hope they make a great couple and so on but...” Pinkie sighed and started to bit her lip.

“What’s that, Pinkie?” Twilight was curious.

“It’s that I haven’t dated anyone since, um, I remember,” Pinkie said and started to sob.

“How’s that even possible?” Twilight couldn’t believe her ears. “You party nearly every night. You should have already met somepony you could date!”

“Yeah but I’m always busy with organizing parties and assuring myself that everyone has a good time that I don’t have time to meet anypony,” Pinkie said sadly.

“Oh, Pinkie. You will finally meet somepony at some other occasion. Besides, you are not alone. Spike has never dated anyone as well.” Twilight grinned.

“AAAAAH! HOW COULD YOU!?” Spike, who overheard the conversation, shouted from inside of the library. He ran upstairs to his basket and hid under a blanket.

“Do you want to tell me that you have dated somepony?” Pinkie didn’t expect that from Twilight.

“Yes,” Twilight said proudly. “But it was long ago.”

Pinkie gazed blankly at Twilight and then cried loudly.

“Um, Pinkie. Please, stop! Please!” Twilight asked Pinkie and then looked around as if looking for some help. “It’s all my fault! That was not an okay thing to say to you! Stop crying and I will do whatever you want, just stop crying!”

Pinkie stopped crying instantly. “Everything?” she asked.

“Well, yes,” Twilight answered with a smile.

“Ok, then date me!” Pinkie said happily.

“Say what!?” Twilight sat on her hindquarters in disbelief.

“Date me!” Pinkie was till grinning.

“But, but, but, you said you didn’t swing that way!” Twilight tried to refuse on the proposal.

“Well, yeah but you are an egghead who couldn’t help me find a stallion to date but you can actually date me!” Pinkie giggled. “This way I won’t be sad that I haven’t dated anypony. Besides, when was the last time you dated somepony?”

“Um, well,” Twilight tried to avoid eye contact with Pinkie. Because she couldn’t find a good answer, she finally gave up. “All right, Pinkie. I’ll date you,” she said resignedly and added nervously: “But nopony can know!”

Pinkie frowned. “Twilight! How could I date somepony who doesn’t want to be seen with me?”

“So, maybe date Spike then?”

“Please, he is a baby! And a dragon. A relationship between a pony and a dragon would never work out!” Pinkie said as if it was something obvious.

“WHAT DO YOU KNOW!?” Spike shouted angrily from inside of the library.

“What’s got into him?” Pinkie wondered but quickly forgot about the dragon and asked Twilight again: “So, where do you want to go, Twilight?

“Maybe, let’s go indide?” Twilight suggested uncertainly.

“Oh, silly. We can’t do that on our first date!” Pinkie laughed. “Let’s go to the restaurant! I’m gonna pay!”

“Oh, horseapples...” Twilight murmured and followed Pinkie.


Pinkie led Twilight to the restaurant. Both mares sat at a table and waited for the waiter.

“What a lovely place, isn’t it?” Pinkie smiled.

“Uh, Pinkie, we eat here quite often,” Twilight said. She was nervous because she hoped that she won’t be forced to do anything that would reveal the fact she was actually dating Pinkie and not just eating dinner with her.

Unfortunately for Twilight, that fact was revealed very quickly. By Pinkie of course. When the waiter came, he asked what they wanted to eat and then Pinkie exclaimed:

“Something special! This is our first date!” Obviously, many ponies overheard that. Twilight blushed and covered her face with her hooves.

After the waiter had gone, Twilight whispered to Pinkie: “You didn’t have to say that.”

“Oh, silly! What kind of a first date would that be, if we didn’t do something special?” Pinkie asked rhetorically.

Twilight sighed and began overhearing conversations. She couldn’t hear everything exactly and was under the impression that everypony in the restaurant talk about her and Pinkie.

“Ohmygosh, ohmygosh, please make it stop, make it stop,” Twilight murmured with a muzzle under her hooves.

“Twilie, our date has barely started! Oh, look! The waiter is coming!” Pinkie exclaimed.

The waiter brought two plates with a half of a heart made of hay and daffodils on each one. Twilight rolled her eyes and facehoofed. “This is not happening.” She groaned. “It can’t be any...” The unicorn bite her tongue as she realized that every time somepony says that cliche, something worse actually happens.

At that moment Rainbow Dash stormed into the reastaurant. “Dinner time!” Rainbow exclaimed. She saw Twilight and Pinkie. “Hiya, girls!”

“I haven’t finished that sentence!” Twilight yelled. Everypony looked at her. “Don’t look at me!” she said resignedly and covered her muzzle with her hooves.

Rainbow flew up to her friends’ table and what she saw confused her a bit. “Girls? Why are you eating halves of heart?” she giggled. “Are you having a date?” Rainbow waited for her friends’ reaction on her joke but instead of nervous denials, she saw Pinkie Pie grinning and Twilight slowly hiding under the table.

“No way!” Rainbow fell on the ground and began rolling on the floor laughing. After a while she bounced back and asked: “No, girls, are you serious?”

“Yeah! That’s my first date ever!” Pinkie exclaimed and hugged Twilight over the table.

“Pinkie, please... Ponies are watching,” Twilight whispered.

Rainbow looked around nervously. “Oh, I, I, I didn’t know that you two, you know, um, swing the other way, so, um, I’ll be going now, heh,” Rainbow Dash said as she was slowly going back toward the door. When she was close to it, she abruptly flew out of the door with a panick in her eyes.

“Gah, now everypony will know,” Twilight whined.

“That’s great, isn’t it!”

“Pinkie. That was going to be only one date. Not two, not three! One!” Twilight was getting angry.

“Sure thing! The only date!” Pinkie acknowledged the number.

“So why do you want everypony to know that we dated! They’ll think we prefer mares! How are we going to find stallions then!?” Twilight started to breathe deeply.

“Hm... Well, I haven’t thought about it,” Pinkie said, “you should have thought about it. You are the smart one in this couple!”

“We are not a couple!” Twilight yelled.

Everypony looked at them again. One of the clients said: “Why do you embarass your marefriend in public? You should solve your problems at home.” Other ponies present in the restaurants nodded in agreement. “You should apology to Pinkie no matter if you dump her or not.” Ponies made agreeing noises.

Twilight gnashed her teeths, took a deep breath and said softly: “I’m sorry, darling.”

“Oh, that’s nothing, sweetie!” Pinkie smiled.

Everypony in the restaurant started to applaud. Twilight was embarrased as she had never been before. “Please, somepony kill me...” she murmured and... began to eat her meal.

“Great date, isn’t it? Pinkie asked after a while. “Firstly, you didn’t want to go, then everypony stared at us and then applauded. How cool is that?”

“Yeah. Cool,” Twilight answered coldly.

“I’m so happy you enjoy it, Twilight,” Pinkie said calmly. “I always wanted my first date to be fun-tastic! And it is!”

Twilight grinned awkwardly. Well, she was helping her friend after all. She repeated in her mind that she was saving Pinkie from being depressed. It kept her sane.

“All right. Now tell me what you like in me!” Pinkie exclaimed.

“Say what?” Twilight was actually too tired to look confused. She just look at Pinkie in disbelief.

“Well, Twilight, you should compliment me. For example, you could say something about my eyes. Or my coat. Or my mane. Do you like my mane?”

“Meh, I like your mane,” Twilight said coldly.

“Oh, you need to put more heart into it!” Pinkie looked leniently at Twilight.

“Gaah, AAAAAAaay looooooooooooove your mane,” Twilight said sarcastically.

“Well, A for an effort.” Pinkie smiled and stuffed her mouth with hay.

Both friends fnished their meals in silence. Pinkie smiled happily all the time, while Twilight was visibly angry and was giving murderous looks around.

“Well, that was great! Now, I should walk you home!” Pinkie exclaimed.

“Might I walk you home instead? You live closer to the restaurant,” Twilight asked indifferently. She knew she’s not going to convince Pinkie.

“No, silly! I asked you out and I gotta walk you home! Let’s go!” Pinkie encouraged her friend to leave the restaurant. After they had went out, Pinke quickly returned to pay the bill.

“That’s my chance!” Twilight thought and galloped away. Unfortunately, Pinkie was already waiting for her hidden behind a wooden crate.

“Where are you going, Twilie? We shall WALK home.” Pinkie giggled.

Twilight sighed. “Okay, let’s get this over with.”

Twilight walked slowly toward her house while Pinkie jumped excitedly around her. At one moment they saw Rarity and Big Mac walking from opposite direction. Big Mac looked like the happiest stallion in Equestria while Rarity, well, was horrified. When both ‘couples’ passed each other, Rarity whispered to Twilight: “Help me!”

Twilight understood her friend. That day was a real nightmare but it was going to end. She decided she was going to think later about probable gossips but they were not important right now. She could alredy see her house what made her feel relieved.

When they finally arrived at the door, Twilight took another deep breath and said: “Well, Pinkie. It was the weirdest date ever. I hope you had a good time. And I hope this was our last date.”

“Okie-dokie!” Pinkie exclaimed. „But there is only one thing left!” Pinkie giggled.

“What now?” Twilight groaned.

“Well. I walked you home, right? Then you we need to kiss each other before I leave! That’s how it usually goes!” Pinkie explained joyfully.

“No way! I agreed on the date, I was embarassed in the restaurant and the whole town is gonna gossip about us for weeks! I’m not gonna kiss you!” Twilight shouted in anger.

“Oh, come on, Twilight! You’ve been through so much today! You’re gonna feel better after the kiss!” Pinkie encouraged her friend.

“I said no!”

“Twilie, Twilie! Pleeeeeease! That’s gonna be my first kiss! I think I should kiss someone special!” Pinkie fell on the ground. Her eyes became wet.

Twilight groaned. “For Pinkie,” she thought and said aloud: “One short kiss. And nopony can know.”

“Sure thing!”

Twilight closed her eyes and leaned forward. She felt disgust. She was not into mares at all. But she was not too assertive as well and now she was about to kiss Pinkie.

She felt even more disgust as she touched Pinkie’s mouth. These few seconds seemed to last forever.

“Gotcha!” Pinkie shouted and began laughing.

“What!?” Twilight opened her eyes. She was touching Pinkie’s elbow with her muzzle. “Pinkie!?”

Pinkie laughed hysterically. “I can’t believe, Twilight! You’re so naive! You really thought I was dating you for real!?” Pinkie giggled. “You are such a crack-up! I had a great time! That was like my est joke ever! Well, see you later” Pinkie trotted away laughing.

Twilight stood in place for a longer while. She couldn’t think of anything.

“T’was a... j-j-joke?” she stuttered and after a few seconds, she went into her house. “Gotta read something before I freak out...” she thought and opened the first book in sight.

THE END

Later at Sugar Cube Corner.

“Pinkie, we need to talk,” Mr. Cake said grimly.

“What’s up, Mr. Cake?” Pinkie asked with a grin.

“Well... Our sales went down recently and, um, how to put it delicate... We need to fire you, Pinkie,” he said.

“Oh, silly. You can’t do that!” Pinkie giggled.

“What? I’m the owner!” Mr. Cake frowned.

“Yeah! But, you know, I’m into mares! Everybody’s seen that! If you fire me, that will mean that you discriminate against me! You know what I mean?” Pinkie said jumping excitedly around Mr. Cake.

"Um, You are ggoing to sue me, if I fire you?" he asked uncertainly.

"Exactly!" Pinkie exclaimed and giggled.

“Oh, horseapples...” Mr. Cake said and closed his eyes.