May The Best Date Win

by GeodesicDragon

Rating: everyone
Tags: Romance, Human
Length: 2253

You, a human, and Flash Sentry both have a crush on Princess Twilight Sparkle. There's only one way to decide which one of you deserves to win her heart.

Cancelled — because, quite frankly, this was the stupidest idea I've ever had.

You have been in Equestria for many years now, and in that time you have seen Twilight Sparkle - the first pony you ever met - change a lot. She has gone from being a small-town librarian to being the Princess of an entire nation — which doesn't do your courage any good when it comes to telling her how much you like her.

But it would seem that you have some competition, as one of her guards is also looking to win her over. When you both proclaim your feelings to her at once, she simply responds by setting the two of you a challenge: "I want each of you to plan, and then take me out on, the best date I will ever experience."

The result is something that all three of you never expected.

Published 1970-01-01 00:00:00 UTC
Last updated 2014-02-04 20:30:08 UTC

Setting The Challenge

CHAPTER ONE

Setting The Challenge

Three years.

It has been three years since you last saw another human. Three years since you last saw your family or friends. Three years since you last worked that dead-end job you once had. Three years since you last had a chance to sleep in. And three years since you found yourself in the land known as Equestria, populated with many pastel-coloured ponies — much to the surprise, shock and horror (in that order) of an entire town full of them.

Sure, these ponies reacted in a funny way to you at first – if trying to throw you in jail could even be called 'funny' – but you eventually managed to convince them that you weren't a 'Diamond Dog', but a simple human who had somehow got lost during a lightning storm on their way home.

As soon as you mentioned the storm, a surprised yelp came from one of the ponies in the group. It parted to reveal a unicorn, who was walking slowly towards you. She was purple, with a purple mane and tail that both had pink highlights running through them. There was a mark on her flank depicting a star surrounded by five more. This, you would soon discover, was Twilight Sparkle — the one who brought you to Equestria in the first place.

She explained that she had been conducting some experiments in weather control to help out the local weather team. Her spell went wrong and created a surge of magic which caused a fair bit of damage – and apparently made one unicorn, a white one, have what she called a 'bad mane day' – but it also had the unfortunate side-effect of bringing you along for the ride.

Twilight was full of apologies, and insisted that you stayed with her until she found a way to send you back. That was three years ago.

But a part of you is glad that she didn't find a way. For the first few months of your new life, you and Twilight spent every waking moment talking. You taught her all about the world that you came from – the world you left behind – and she taught you all about the world which you now called home.

You also taught her much about human history, politics, technology, science, faith... everything. In return she taught you about the history of the three kinds of pony, their troubles and strife, their eventual unity and then everything which happened up until the very moment you arrived in the middle of Ponyville.

Suffice to say, it was a rather long lecture — but you didn't mind. After all, you were learning new things from a species you thought only existed in ancient myths and legends. Who else could say that they have experienced the same thing?

Fast forward a few more months: Twilight's experiments are yielding little to no results, and your hope of returning home is fading fast. Yet she was always there with a warm smile and a comforting word or two.

"I'll get it eventually," she'd say. "Just you wait."

But it all soon became too much. Far too much time had passed, and with no progress. By all rights you had been declared legally dead back home. Your apartment would have been cleared out to make way for a new tenant, and your job would have gone to someone who could actually show up and do it.

With a heavy heart, you asked Twilight to cease her efforts. She was determined not to, but relented once you explained why. As you finished speaking she began crying — as well as berating herself for 'ruining your life', as she put it.

You were shocked that she would think that way, and began trying to calm her down. You explained that yes, she had taken you away from your old life — but she had brought you to a new one, and given you things you never thought you'd experience.

She smiled upon hearing that and hugged you. But as you returned it, you began to feel yourself getting slightly warmer. You put it down to emotions and shrugged it off, content to simply sit there and hug your first – and best – friend in Equestria.

As the days and months ticked by you tried your best to forget all about your old life, focusing instead on your new one. Your friendship with Twilight grew, and you often found yourself accompanying her and her other friends – the bearers of the Elements of Harmony – on their various adventures.

But it was during preparations for her brother's wedding that you realised your true feelings for the unicorn. Twilight was adamant that his soon-to-be wife, Cadence, was a fraud who was up to no good— and you were the only one who believed her. After crashing the rehearsals, the two of you were shunned by everypony else present — which included one of Equestria's Princesses.

They left the room in disgust as Twilight fell to the ground, sobbing uncontrollably as Cadence strolled over.

"Cadence," she whispered. "I'm so sorry."

"Same here," you added. "I'm sorry."

Cadence simply grinned wickedly. "You will be," she hissed. Her horn flashed with light, and darkness overtook you.

You both woke up in an underground cavern, images of Cadence mocking you from the walls. Twilight shot magic at them and succeeded in breaking a hole in one — revealing a very dishevelled and malnourished Cadence. Twilight leapt at her, ready to attack, only for this Cadence to begin reciting the rhyme she and Twilight did together when the latter was a filly.

It soon dawned on Twilight that this was the real Cadence, and that the one above was indeed an impostor. After escaping from the caverns, the three of you gatecrashed the wedding — and revealed the truth to all those present.

The fake Cadence unveiled her true form as Chrysalis, Queen of the Changelings. Her plan had been to weaken Shining Armour, Twilight's brother, so that her army could take over Canterlot. Princess Celestia stepped up to defend her subjects, but was defeated by Chrysalis in single combat. Before passing out, the Princess asked Twilight and her friends to fetch the Elements. They nodded and ran out of the room, with you in hot pursuit and Chrysalis' mocking laughter echoing in your ears.

As you ran, the shield Shining had put up around the city was broken — and hundreds, if not thousands, of Changelings began pouring in. The Royal Guard were hopelessly outmatched and soon the invaders had taken over a large portion of the city, including the vault where the Elements were kept.

Twilight and the others refused to go down quietly and got ready for a fight. You cracked your knuckles and got ready as well — only for the Changelings to assume the forms of your friends.

"I'd like to take this opportunity to apologise to you all in advance," you said. "Because I think I'm going to end up punching one of you sooner or later."

With those words, the Changelings rushed you. You moved to meet them, arms and legs flailing like pistons. Shaking off the fact that the Changelings looked like your friends, you began cracking skulls and taking names.

You opted for self-defence, knowing that none of your friends would willingly attack you. As a result, anypony who came charging at you soon got a taste of the business end of your size tens. The Changelings soon decided that you were more of a threat, and began swarming you with numbers in an attempt to take you down.

And it worked. You couldn't cope against so many, and soon fell to their attacks. Defending yourself as best as you could, you prepared to meet your Maker.

But then a loud cry of anguish echoed across the area. The Changelings attacking you were blown off by a blast of purple magic — Twilight's magic. The mare in question rushed over and stood in front of you protectively, nostrils flaring and horn glowing.

The last thing you felt before you passed out from the pain was your heart soaring.

You woke up in the hospital an unknown period of time later to find Twilight sleeping on the bed with you. A doctor came in, pleased to see you sitting up, and explained what had happened.

After you had passed out, you and the girls were taken captive and brought back to Chrysalis. While the Queen was going on about how great her scheme was, Twilight broke free of her imprisonment and sneaked over to Cadence, freeing her as well.

Cadence then used her magic to free Shining Armour of the spell Chrysalis had cast on him to mess with his mind — and then, using the power of love itself, the two of them blasted the Changelings out of Canterlot and into the unknown.

Needless to say, it was one hell of a show — and you missed it. The  doctor went on to explain how Twilight had rushed over to you and teleported you straight to the infirmary, where you had stayed for nearly two weeks.

And also that she hadn't left your side once.

You knew then what that feeling you had felt was. No longer did you see Twilight Sparkle as a mere friend. You saw her as somepony you could trust your very life to, somepony whom you would do the same for in a blink of an eye.

You were in love with her.

Several months passed and Twilight was given the task of finishing an ancient spell, started by Starswirl the Bearded. After fixing up a few incorrect cutie marks along the way, she aced the test.

And then she simply vanished, blasted away by the Elements of Harmony in a blaze of light. You searched high and low for her, only snapped out of your stupor by a bright light in the sky. It touched down to reveal Twilight — who then revealed the magnificent lavender wings which now adorned her back.

The coronation was last week, and now you find yourself in your new position as Princess Twilight's second assistant. This has only made your plan to tell her how you feel that little bit difficult.

How in the hell are you supposed to tell a Princess that you're in love with her? Will she think you're playing a joke? Will you end up falling out with her? Will she even care?

You look around the throne room. Twilight is sitting on the throne, addressing a few ponies who have requested an audience with her. And then you see... him.

Flash Sentry, one of the guards assigned to protect the new Princess, has been acting odd. Any chance there is to get close to her, he takes it. You have also heard rumours that he's been practising chat-up lines in the barracks.

He's in love with her as well, and the smug grin on his face tells you that he's about to admit it. He probably thinks he doesn't have any competition. Time to prove him wrong.

As the last petitioner leaves the room, Flash grins and saunters over to where Twilight sits with a small smile on her face. You also walk over and listen as he addresses her.

"That was the last of your petitioners, Your Highness," he says with a bow. "Is there anything I can do for you?"

"No thank you, Flash Sentry," Twilight replies, glancing at a checklist she keeps on a table next to her. "I don't have anything else to do, so I am going to call it a day."

"As you wish, Your Highness," Flash says. "However... there is something I have been meaning to tell you."

"So do I," you butt in. "And it's something important... something I should have told you a long time ago."

"Excuse me," Flash says through gritted teeth. "I was speaking to the Princess first. Wait your turn."

"I'm her assistant," you shoot back. "You're just a guard, so I have more authority to speak to her than you do."

"Be that as it may," Flash growls. "But I was still speaking first."

You glare at each other for a moment before you both turn to Twilight and shout at her in perfect unison:

"I love you, Twilight!"

Her jaw drops and her cheeks flush red at this sudden proclamation from her best friend and her guard. You and Flash, meanwhile, start getting in each others faces — pushing and shoving the other in a vain attempt to assert your dominance.

You hear the soft hum of magic as Twilight picks you both up in her levitation aura and separates you. "I had no idea both of you felt that way," she says softly, before looking directly at you. "Especially you. Why didn't you tell me sooner?"

You shrug. "I guess I was nervous," you reply. "But it's true, Twilight, I love you with all my heart."

Flash goes to say something, but Twilight stops him. "There is only one way to settle this," she sighs. "Only one way to decide which of you deserves to win my heart." She pauses for a brief moment. "I want you both to plan, and then take me out on, the best date I will ever experience."

You and Flash glare at each other again. Challenge Accepted.