How NOT to Confess to an Alicorn (or anypony, really)

by Hyper Star

Rating: everyone
Tags: Romance, Comedy, Rarity, Pinkie Pie, Twilight Sparkle, Slice of Life, My Little Pony: Friendship is Magic
Length: 1649

If something works in old cheesy romance novels there’s no way it can’t work in real life, right?

Pinkie asks for Rarity’s help confessing her feelings to Twilight. Rarity is an avid reader of old romance novels, naturally this means she thinks she knows exactly how to charm a pony.

This can only go wrong.

Random story I wrote, matchmaker Rarity is very fun to write.

Inspired by Leave No Trope Unturned

Published 2024-04-04 09:50:01 UTC
Last updated 2024-04-04 09:50:01 UTC

Hyper Star Presents: How NOT to Confess to an Alicorn

“That is your crush?”

“Mhm.”

“Is this another prank?”

“Nope.”

“Well... I never thought bookish alicorns from Canterlot were among your tastes! You seem like somepony who’d want someone a little more like you, like Rainbow Dash.”

“Is that a compliment?”

“I did not mean to offend her or you, darling, I’m just... surprised, but oh well, you know what they say, opposites attract. Shock aside, this is wonderful news! I take it you need my help confessing to her?”

“Yeah!”

“But how did this all come to pass?”

Pinkie let out a sort of wistful sigh, “It just happened, you know? I’ll tell you, ever since–”

“Ah, ah, stop, darling, what are we doing? This is no time for stories! You can tell me later.”

“Oki doki.”

“I have read millions of romance novels,” Rarity continued

“That’s a good thing, ri–?”

“I know exactly what to do! It will be amazing!”

“Rari–?”

“Come along now! No time to waste!”

“All right, darling, it’s simple, what you need to do is just give her the cupcakes you baked.”

“That’s it?”

“Yes, why?”

“Uh... when I said subtle I didn’t mean *that* subtle; how can she tell these are a confession?” Pinkie Pie held up the box of cupcakes, scrutinising them.

“They’re pink and purple with hearts on them and a note attached saying 'I love you', I cannot think of anything *less* subtle!”

“If you say so.”

Pinkie Pie peeked in to the window of Twilight’s castle library, she slowly opened it and placed the cupcake box on the windowsill.

“There, now you must wait for her to find them, she’ll come to talk to you about it, and you’ll have the perfect moment to sweep her off her hooves!”

“Should I do that?”

“Metaphorically, darling.”

━━━━━━━==♡☆⊱✿⊰☆♡==━━━━━━━

“Make sure not to drop any, Spike!” Twilight said, placing various books and scrolls down onto a table.

Spike stumbled into the room, carrying an equal if not larger amount of items.

Twilight looked over to the window, she noticed a small box placed on the windowsill, she levitated it from there to in her hooves. The box was from Sugar Cube Corner.

“Is that from Pinkie Pie?”

“Must be. That’s weird, I don’t remember ordering anything.” she opened the box it had two pink and purple cupcakes with frosting hearts on them, “She really is something isn’t she?” she looked fondly at the note attached.

Spike rolled his eyes, “Yeah, yeah, would you mind helping me up?” he said from under a pile of books and scrolls.

━━━━━━━==♡☆⊱✿⊰☆♡==━━━━━━━

“Well that’s strange,” Rarity said, peeking in from the castle library’s window.

“What? What happened?”

“She didn’t even bat an eye at the cupcakes nor the note. Perhaps our dear Twilight is a lot more romantically inept than I had assumed.”

“Oh, yeah, uh... is it too late to mention I always make pink and purple cupcakes with hearts on them for her?”

“That was information I could have used a long time ago.”

“What? She’s pink and purple and I make hearts on everything! Don’t you remember your birthday cake?”

“What about the note?”

“'I love you' doesn’t necessarily mean you love somepony romantically, I’m always telling ponies how much I love them.”

Rarity sighed, “Not to worry, Pinkie, we shall try again.”

“Plan B, listen, I am going to set you two up on a picnic, a date, if you may–

“D– date?! W– we’re not even–!”

“Don’t interrupt, darling, I shall tell Twilight to come on a picnic, on which I will not show up, leaving her and you alone. You can enjoy some friendly bonding time and when it’s all done, you will be feeling comfortable enough to ask her out!”

“I dunno, that sounds like something that would happen in a fanfic, speaking of that, when did this actually work for somepony?”

“Well... I mean... it must have once or twice...”

━━━━━━━==♡☆⊱✿⊰☆♡==━━━━━━━

Twilight waited by the tree Rarity had instructed her to, she was being quite vague as to why, and to add to her confusion there was a picnic blanket laid here, perhaps it was just a weird way of asking her to get some fresh air?

“Oh, hi Pinkie.”

“Hi Twilight!”

“Did Rarity send you here too?”

“Mhm,”

“Did she say why?”

“Uuuhh... no... hey, Twi, I’ve been meaning to t–”

“Oh, hi Twilight, hi Pinkie.” Fluttershy greeted them.

“Hey, Fluttershy! Care to join?” Twilight motioned beside them.

Pinkie looked at the bushes behind them from where Rarity was observing, Rarity was desperately trying to get Fluttershy’s attention, making various gestures and mouthing the words 'No!' and 'Go away!'

“If it’s not too much trouble, then I’d love to.” Fluttershy sat down with them, oblivious to Rarity’s signals.

“Great, Rarity should probably be turning up sooner or later.”

━━━━━━━==♡☆⊱✿⊰☆♡==━━━━━━━

“Why didn’t you tell Fluttershy to leave?!”

“Sorry! But, what if both she and Fluttershy got mad at me for telling her to leave like that?!”

Rarity took a deep breath, “Okay, okay, no worries, darling, it’s time for another approach.”

“You see this, Pinkie? This is a potion.”

“Ooh, so that’s why you went into the Everfree Forest. how’s this gonna help me?”

“It is a love potion.”

“Love potion?! No, no, no, Twilight told me how dangerous love magic can be! That thing the Cutie Mark Crusaders used, the Want It Need It spell, it can make *HUGE* problemos!”

“No, no, darling, this is not a love potion per se, it simply boosts confidence to help ponies express their feelings.” Rarity handed her a bottle filled of pink liquid. “Now, you must–”

Spike exited Twilight’s castle, holding a quill in his mouth since his hands were too full of scrolls. The feather of the quill tickled his nose, which after a while caused him to sneeze, lighting the scrolls on fire. “Oh boy.”

Pinkie looked around and finding nothing of use, poured the potion bottle onto the scrolls, extinguishing them.

Pinkie and Spike sighed in relief while Rarity did in disappointment.

“Hey, what is this stuff anyway?” Spike picked up the bottle and took the last sip remaining.

“Uh, Spike, maybe you shouldn’t–...”

Spike licked his lips, shrugging. He turned to walk away but suddenly his eyes dilated and slipped into a dreamy state.

“Spike?”

Spike turned towards Rarity, “Oh, Rarity, have I ever told you how beautiful you look? I mean, I have never met a more amazing and generous and pretty than y–”

“Seems like we need Plan D. Let’s leave, the effects should wear off after a while.”

“Now this one is one of my favourites. Twilight occasionally stargazes, right? The protagonist — in this case Twilight — is sitting all alone of the balcony, that is until, her lover, or atleast the pony who *will* be her lover — that is you — arrives on her balcony to sweep her off her hooves — again!”

“I dunno, Rarity, your last two plans failed pretty ba–”

“Hush, darling, now do you know where to find flowers at this time?”

━━━━━━━==♡☆⊱✿⊰☆♡==━━━━━━━

Pinkie wasn’t quite sure what exactly Rarity was imagining when she said 'Twilight’s balcony', there wasn’t any ground to stand on, so she now found herself hanging from it since the balloons she used to get up there had all popped, to top it all off she had dropped the bouquet Rarity told her would be 'perfect for Twilight!'.

Rarity sighed, coming out of her hiding spot to help Pinkie, that is until Twilight came out onto the balcony, to which she retreated to her vantage point.

“Twi? Could you, uh, help me out?”

“Pinkie? What are you doing?”

“... Nothing.”

“Okay, I’ll try pulling you up, hang on.”

“Yup, doing that already.”

Twilight pulled her up onto the balcony, falling backwards and now having Pinkie standing over her.

Twilight blushed, “Uh, would you mind...?”

“Sorry!” Pinkie moved off of her.

Rarity smirked, watching from below, this plan seemed to be going smoothly.

“So, what brings you here?”

“Just thought I should...” Pinkie looked down at the bouquet she had dropped, “... come visit.”

“Oh, well I was–”

The flowers Pinkie had dropped suddenly levitated onto the balcony, surrounded by a blue glow and was set in front of them.

“Weird, that looked like Rarity’s magic, right?” Twilight asked, poking the flowers.

“Wait, Twilight, I have something to tell you...”

Yes.

“Oh, well, I might too...”

Yeees.

“Twilight! Letter from Princess Celestia!” Spike called out.

No. Why am I not surprised.

“I– I better go see what it’s all about, tell me tomorrow!” Twilight walked off.

Rarity facehoofed. “Plan E then.”

Ah, a brand new day and a brand new start, why her last plans had gone so badly, they had decided to call it a night! But these new ones will surely work exquisitely. Pinkie should be arriving any time s–

“RARITY!” Pinkie flung open the door and bounced over in front of her, “Rarity! Rarity! Rarity! Rarity!” she pranced in place, looking even more giddy and joyful than usual.

“Erm yes, darling?”

“SHESAIDYESHESAIDYESSHESAIDYESSHESAID–”

“Pinkie Pie, calm down, and say it slowly and once.”

“She said yes! Twilight! I asked her!”

“Wh– but how did you do it?”

“Oh, y’know, I said I wanted to talk to her and then I told her how much I loved her in a more-than-friends way and I really really wished that she would go out with me on a date!”

“You mean you’re...?”

“Yeah! I guess this means we’re dating now!” Pinkie squealed, “I can’t believe I actually get to say that! She immediately said that she does too and that she’d love to!”

“So you just walked up to her?”

“Mhm!”

...

If that worked, perhaps her Plans E, F and G were a bit too much.