• Published 23rd May 2022
  • 522 Views, 15 Comments

Twilight's Dating Diary - qiley



Twilight's single, and she wants to do something about it.

  • ...
2
 15
 522

I'm Single?!

Something terrible had just dawned upon Twilight. It’s more terrible than the dragons attacking Equestria (if that would ever happen). It’s more terrible than the day Twilight found out Nightmare Moon was real. It’s more terrible than if Cozy Glow, Tirek, Queen Chrysalis, and Sombra all came back with Grogar to attack Equestria at once. It’s more terrible than quesadillas (and that’s saying something, at least for Twilight).

“I’M STILL SINGLE!” Twilight shouted in the vacant Friendship Map room, slamming her head onto the map.

A few moments later, the large double door creaked open, Spike and Starlight both entering the room. In front of them was Twilight, face still stuck on the map.

“Uh, Twilight, we heard a shout and a loud slam, so we thought we’d check up on you,'' Starlight chuckled awkwardly. “Everything alright?”

Twilight slowly faced their direction, her head still on the table. She stared at them, not saying a single thing.

“I don’t think everything's alright,” Spike whispered to Starlight.

Starlight sighed, the two of them approaching the map. Both Spike and Starlight took a seat in one of the thrones, and looked at the slumped alicorn.

Starlight cleared her throat, going into counselor mode. “So, what seems to be the issue, Twilight?”

“I’m single,” Twilight said so quietly that Fluttershy would be proud.

Starlight smiled. “I’m sorry, what was that?”

“I’m single,” Twilight repeated, slightly louder.

“Maybe a little louder?” Starlight held her smile.

“I said, I’m single,” Twilight repeated, still barely audible.

“One more time for me?”

“I SAID I’M SINGLE CELESTIA-DAMNIT!” Twilight shouted.

“That’s what you’re so worried about?” Spike tilted his head. “I thought Equstria was going to get blown up or something. I’m out of here!”

Spike hopped out of the throne, waddling out of the room.

“So, you’re stressed that you’re single?” Starlight repeated.

“Yes,” Twilight sighed, sitting up. “I know it’s stupid.”

“It’s not stupid, Twilight,” Starlight reassured her. “No problem is stupid to me. So tell me, what prompted you to get so bugged by this? It didn’t seem to be a problem to you before.”

Twilight sat up straighter, getting comfortable in the throne. “Remember when I went to visit my parents the other week?”

Starlight nodded.

“Well, one thing led to another, and my parents started talking about how they wanted more grandfoals,” Twilight frowned. “They looked at Cadance and Shiny, then me.”

“Okay…” Starlight replied mindlessly.

“Then they started asking me if I was seeing anypony or if I was interested in anypony, so I answered honestly of course.”

“Uh huh…”

“Then that was the end of the conversation,” Twilight finished.

“I’m assuming you didn’t think much of it then, but when you got back you suddenly started thinking about it more and more?” Starlight asked.

“Exactly!” Twilight huffed. “I thought about how I was getting older. I mean, I have a niece already! I’m not the young mare I used to be. In a few years no pony would want me!”

Starlight rolled her eyes. “Twilight, you’re being a little dramatic.”

“I mean, I was just too busy to think about things like this!” Twilight continued on, ignoring Starlight’s comment.

“Twilight.”

“If I don’t find somepony soon I’m going to die lonely, then I’ll be known as the princess who died without getting hitched. Imagine that? Dying just to be known as the virgin princess. That would be-”

“TWILIGHT!” Starlight yelled, shutting the alicorn up. “As I said earlier, I think you’re being a little dramatic.”

Twilight sheepishly smiled, rubbing the back of her neck. “Maybe I was.”

“No, you were,” Starlight simply smiled.

Twilight took a deep breath, exhaling it slowly. “You’re right. Thank you, Starlight.”

“Of course,” Starlight said. “Now that you’re calm, let’s continue discussing.”

“Okay,” Twilight sat up straight.

“Now Twilight, from what I understood from your little rant, you want to find your special somepony.”

Twilight nodded.

“But you’re worried that you’re not going to find them, and end up all lonely.”

“Exactly!” Twilight exclaimed. “You’re right on the nose, Starlight.”

Starlight smiled. “So what are some solutions you can do to prevent that from happening?”

“Make a stallion version of myself and date it?” Twilight suggested. “Or just a clone of myself. I’m not one to discriminate.”

“I don’t think that’s the most rational answer,” Starlight chuckled. “I’m not one to talk about being rational, though.”

“No, you’re right,” Twilight sighed. “I think the most reasonable answer is to go out and try and find somepony.”

“That would be a step in the right direction,” Starlight nodded. “I’m sure there’s a lot of ponies who would love to be with you.”

“I doubt it,” Twilight said dejectedly. “Ponies probably think I’m a nerdy bookworm.”

“Do you even hear yourself right now?” Starlight cocked an eyebrow. “First of all, you're a princess of Equestria. That already puts you above a lot of ponies. Secondly, you’re pretty attractive. You have a nice figure, although you have been getting a little pudgy recently.”

“I’ve been a little stressed,” Twilight snorted.

“Oh really?” Starlight smirked. “Anyways, not only do you have a good figure, you’re also a beautiful mare.”

“You really think I’m beautiful?” Twilight asked.

“Yeah,” Starlight shrugged. “I’m sure everypony thinks you are.”

Twilight nodded silently.

“Lastly, you’re smart. Like really, really smart. I’m sure you could solve all of Equestria's problems if you were given enough time and enough resources,” Starlight said. “And that’s not even everything that’s great about you. I mean, you forgave Discord and I after the things we’ve done!”

“I never thought about myself like that,” Twilight said, looking down.

“As I said before, there’s lots of ponies that would love to be with you,” Starlight placed a hoof on Twilight’s shoulder. Twilight looked up to Starlight, who was smiling warmly. “You just have to find the right one.”

“You’re right,” Twilight smiled back.

“I know,” Starlight chuckled, sitting back in her chair.

“But how will I find them? There’s a lot of ponies in Equestria,” Twilight said, worried.

“You could, I don’t know, go on some dates?” Starlight suggested. “That would be a good start.”

“You know, I never thought about that,” Twilight chuckled.

“No wonder you’re still single,” Starlight mumbled.

“Hey!” Twilight frowned, crossing her forehooves. “I heard that.”

“I know,” Starlight replied. “As for finding the ponies, how about you compile a list of ponies you were even somewhat attracted to? I’m sure you can do that, knowing how much you love lists.”

“That’s a great idea!” Twilight’s face brightened up. “You’re on a roll today, Starlight.”

“Heh, thanks,” Starlight smiled at the compliment.

“I’m going to get a scroll and quill, I’ll be right back!” Twilight enthusiastically hopped out of her throne, trotting out the room. Starlight was left there by herself for just a bit before the alicorn came trotting back in, a grin on her face. She levitated the quill and scroll onto the map, taking a seat.

“So, did you think of anyponies on your way back?” Starlight asked.

“A few. I wrote their names down already,” Twilight slightly blushed. “This is kind of embarrassing now that I think about it.”

“You aren't going to back out, are you?”

“No, of course not,” Twilight sighed. “If I want to change, I have to be ready to be uncomfortable!”

“That’s the spirit,” Starlight smiled. “So, who do you have in mind?”

“Well, the first ponies that came to mind were the girls,” Twilight said. “They were my first friends, and I wouldn’t mind being with any of them.”

“That makes sense,” Starlight nodded. “Starting out with ponies you're comfortable with is definitely a smart move. Don’t want to jump head first into it.”

“That’s exactly what I was thinking!”

“I think you may have to cross Pinkie out though,” Starlight chuckled. “I heard she’s already dating Cheese Sandwich.”

Twilight crossed out Pinkie’s name. “Fair point.”

“Alright, who else?”

“I know it might sound weird, but I put Discord down,” Twilight said.

“Do you two even talk?” Starlight cocked an eyebrow.

“We do,” Twilight paused. “Occasionally.”

“Uh huh…” Starlight nodded slowly. “I mean, I’m not against it, but as you said, it sounds a little weird.”

“Let’s just move on then,” Twilight dryly chuckled. “Next I put Celestia and Luna.”

“Can’t say I’m surprised,” Starlight said. “Especially with Celestia.”

“Heh, yeah,” Twilight sheepishly smiled. “I had a little crush on her a while back.”

“And for Luna?”

“I think she’s cool and fun to talk to,” Twilight shrugged. “So why not?”

“Alrighty,” Starlight simply said.

“Next up is…” Twilight looked down at the list, then up at Starlight. “You.”

“Woah, can’t say I was expecting that,” Starlight grinned.

“I mean you’re also my good friend, so I kind of just mindlessly put you down like I did with the girls.”

Starlight nodded. “I mean, it makes sense. I’m not against trying something either.”

“That’s reassuring,” Twilight smiled.

“How many more names have you jotted down?”

“Just a few more,” Twilight answered. “I’m sure I could think of some more later, but these are all the ponies I thought of so far.”

“Arlight, let’s just rapidfire the last few then,” Starlight suggested.

“Sounds good,” Twilight nodded, taking a deep breath. “So the rest of the ponies are Sunburst, Sunset, Cheerilee, Trixie, Flash Sentry, Ember, Thorax, Tempest, Spitfire, Soarin, Thudnerlane, Cloud Chaser, and Flitter.”

“Woah, that’s actually a lot of ponies,” Starlight chuckled. “Wait, actually not all of them are ponies.”

“I don’t discriminate.”

“You’re telling me you found all these creatures somewhat attractive?” Starlight asked.

Twilight shrugged. “I guess. I kind of just thought of the friends I’ve made over the years.”

“Well with this many ponies, it’ll take a while,” Starlight chuckled. “I’m sure you won’t have to think of any other pony to write down for a while.”

“I definitely will write down some more,” Twilight said. “I’m sure there’s some ponies I’m missing.”

“Well now that you’ve got your list, you just have to choose one to ask on a date!” Starlight clapped her forehooves together. “Though, that’s easier said than done, though.”

“I’m getting nervous just thinking about it,” Twilight muttered. “Imagine the princess of Equestria, getting nervous over something as simple as this.”

“I wouldn’t say it’s that simple,” Starlight said. “I mean it takes a lot of courage, that’s for sure.”

"I guess you’re right,” Twilight smiled weakly. “I think the easiest way would be just to go from the top to the bottom.”

“Well that would definitely make choosing less of a pain.”

“That’s for sure,” Twilight said. “Guess that means I’m staring with one of the girls.”

“It’s settled then!” Starlight said. “So, who’s at the top?”

“It’s…” Twilight looked down at the list. “Well, it would’ve been Pinkie Pie but next up is Fluttershy.”

“Oh boy, that sure is going to be fun,” Starlight snickered. “I can’t imagine what Fluttershy’s like on a date.”

“I’m not sure if she’s ever been on one,” Twilight tapped her chin. “I don’t recall her ever saying anything during our spa talks.”

“Wait, what do you girls talk about at the spa?” Starlight cocked an eyebrow.

“Just simple gossip,” Twilight answered. “It’s mainly led by Rarity.”

“Of course,” Starlight rolled her eyes.

“So when should I ask her?” Twilight said. “I don’t know how to really bring up anything like this. Maybe I should read a book or something?”

“A book will only get you so far, experience will definitely help more,” Starlight said. “I’d say just be ready for a bit of awkwardness and stiffness at first. It’s definitely not going to be easy.”

Twilight sighed. “You’re right. Guess I’ll just have to suck it up and ask her.”

“You two are having tea soon, right?”

Twilight nodded.

“Why not do it then? That would be a perfect time to bring it up, since it’s just the two of you.”

“I guess I could…” Twilight said slowly.

“Just go for it Twilight,” Starlight smiled, placing a hoof on her shoulder. “Just be you and everything will be alright.”

“You’re right,” Twilight smiled back, resolve and determination in her eyes. “I can do this.”

Author's Note:

That's the end of the first chapter of my newest fanfcition! Chapters will usually be around 2500-4000 words long. I'll try and update the story every two to three weeks, but that depends on both my motivation and work schedule. :twilightsheepish:

This story will be very slice of life. It's mainly just Twilight interacting will alot of ponies (and creatures) one-on-one, trying to find her special somepony (or somecreature). So that means there will be all kinds of Twilight ships here! I hope you all are as excited as I am! I can't wait to write the upcoming chapters.

Feel free to comment and constructive criticism you have, or anything else you have to say about the story.

See you all in the next chapter :twilightsmile: