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Following the events of "Traveler," Twilight goes to Canterlot to deliver her report on what has transpired since the Doctor's arrival in Ponyville directly to Princess Celestia. She leaves the Doctor in Spike's capable claws, asking him to show Equestria's newest arrival around town while the TARDIS rests and repairs itself from the trials of the previous day.

Although at first distraught at being stranded in the seemingly serene township of Ponyville, the Doctor finds himself reexamining his initial assumptions about the ponies, the land of Equestria, and his compulsive need to travel when he is confronted with the miraculous, impossible events surrounding Ponyville's resident party mare: Pinkie Pie.

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The Pinkie Conundrum is the first in a series of continuity branching off from the foundations established by the Doctor Whooves stories: Number 12 and Traveler by the very talented Squeak-anon and all references to these two works of fanfiction is credited to him. Also, while this is a separate continuity from any future works by Squeak-anon, it is strongly recommended to read these two fictions before reading Pinkie Conundrum.

This work has been developed and published with permission and blessing of Squeak-anon, my original inspiration.
Doctor Whooves Intro posted on YouTube by: Cshep99
Cover art provided by FoxInShadow from deviantart.com
Proofreader, Editor and Number One Assistant: 2dextreem

If you enjoy this story as well as my other works, please leave a comment. Constructive critique is encouraged as well as any questions or remarks that may occur.

Chapters (7)
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==Originally written spring 2011== Equestria Daily Post==
GLaDOS is free of Chell, free to continue testing, when she discovers a portal gun Wheatley tried to repair with duct tape. When the portal gun catastrophically fails, the enrichment center, GLaDOS, and Chell are literally dropped in the middle of Equestria. The mute test subject soon finds the world of ponies far more welcoming than the human world. But GLaDOS sees possibilities. Let the testing begin... for science.

Chapters (10)
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Sunset Shimmer has always been a hot-headed, impetuous girl. She's always been prone to making snap decisions, and later finding herself regretting them. It was exactly this temperament that had brought her to the human world, penniless and alone. When the opportunity to get back on her feet presented itself in the form of a stranger's outstretched hand, she leaped at the chance.

This is the story of a woman who has made many bad choices, and the life those choices have made for her.


Tags, and even rating, may change as the story goes on.

Thanks as usual to Magello for the cover art!

Chapters (13)
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A lone vampire bat sneaks through the mirror portal and ends up in the human world. Instead of apples, it now craves something far richer. And unfortunately for Sunset Shimmer, she's its next snack.

Sunset can't remember any of her activities past sundown. The light hurts not just her eyes, but burns her skin. And she's thirsty.

So very thirsty.

It's up to the Rainbooms to save Sunset from herself before she drinks the whole city dry. Too bad Twilight Sparkle is her primary target.


Thanks to Saro0fd3monz for the inspiration!

Edited by DrakeyC and HenryAnthonyCourtler

Now with a TVTropes page!

Now with a French translation!

Chapters (10)
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While lounging around Twilight's castle and airing some friendship-related grievances, Discord stumbles across a magic book containing letters from an inter-dimensional pen pal. As it just so happens, this pen pal also had sinister designs for Equestria, but was quashed by the Elements of Harmony. What's more, she's made amends since that day, and she's now Twilight's friendship student. Eager to bond with someone who can relate to him on a personal level and grow into a better draconequus, Discord packs his bags and heads off to the human world with Twilight's semi-blessing. His mission: Befriend Sunset Shimmer.

However, his plan has a bit of a snag. See, Sunset hasn't been keeping up with Equestrian events, and she never got the memo about Discord turning over a new leaf. As such, she believes that his sudden appearance doesn't bode well for Equestria, Canterlot High, or herself. Not only this, but the Sirens are privy to Discord's return as well, and they see this as a golden opportunity to bounce back from their own recent defeat. Well, Adagio does, anyway. Sonata doesn't want to live in a world that makes no sense, and Aria would rather maintain what little dignity she has left by not getting involved (or so she claims).

So while Discord is trying to earn Sunset's trust and show her what a good friend he is now, Adagio is trying to get in on an evil scheme that doesn't exist. And while that is going on, Sonata is appealing to the Rainbooms behind Adagio's back, hoping that they'll make Discord go away. With so much miscommunication thrown into the mix, you just know that hijinks are inevitable. Good thing Aria made popcorn.

Cover art provided by the amazingly talented Neighthirst.

Chapters (14)
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While relaxing after a performance, the Rainbooms discover Sunset has scars that she definitely didn't have before the Fall Formal.

As of 9/14/2015, this story has a dramatic reading by Goombasa. Give it a listen!

7/7/2016: Now with cover art designed by the very generous Novel-Idea! Thank you so much!

7/23/2016: This story has a reading by Gabriel C Media. Give it a listen!

Chapters (1)
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Twilight had planned to visit Sunset Shimmer and her friends over in the other world for a nice, quiet weekend, away from all the worries and problems associated with being a Princess of Equestria. Unfortunately, things rarely go as planned.

After an accident cuts her off from Equestria, Twilight finds herself stuck in the human world until the gateway between the two worlds can be fixed. Which wouldn't normally be a problem...

...If she wasn't still a pony.


Now with TvTropes page!

Cover art
Proofread by Dusty Old Qrow, RQK, Dusty Tomes (Ch. 2), Emtu, and Doctor Candor.

Chapters (15)
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The wheel of time turns, as destiny and history clash together.

Fifty years into the future, Sunset Shimmer is Princess Twilight Sparkle's most faithful student. She is smart and eager, but doesn't always think things through. Her life had been perfect, right up to the End of the World.

With a ruined future, Sunset travels into the past to alter the course of history. With only her mentor's cryptic word to go on, Sunset and the Elements of Harmony must solve the riddle of the Dark Regalia and stop the mysterious Vesper Radiance from rising to power. But the further Sunset goes, the more she feels like she's been through it all before.

Is destiny set in stone, or can Sunset shape her own future? Only time will tell.

Featured on Equestria Daily 6/16/13
Gratefully edited by JustAnotherTimeLord, Icarus_Gizmo, Cerulean Voice and Bad_Seed_72

The Sunset of Tropes page!

Chapters (27)
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Life is looking up for Sunset Shimmer.

With her grandstanding at the Battle of the Bands, Canterlot High has taken a new approach to her. Amends have been made, friendships have been restored, and Sunset is on the fast track to becoming a better person.

But even now, there are still apologies that have to be said.

For her Spring Break, Sunset returns to Equestria to make up with her estranged family: the parents that raised and provided for her, and the sister she left behind. But a lot has changed since then, and some wounds won't heal by just saying 'I'm sorry.'

Fixing friendships is one thing. Sunset will be put through her hardest test yet when she tries to bring her family back together.

Another one edited by Cerulean Voice.

Stunningly amazing cover art drawn by Ayemel!

Featured on Equestria Daily.

Listen to the audio book here!

Chapters (11)
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Part of The Destiny of the Ancients

When one door opens another closes down, but what happens behind those closed doors? What if you could find out what other surprises destiny had for you behind them?

My name is The Observer, I have existed even before Celestia and Luna, I have found an anomaly and that one is Sunset Shimmer, the first of pony kind to not only travel and reside in another universe, but also a being that has always been shaping and molding destiny around her, a being full of mysteries and danger.

The rules of the game have changed and the multiverse as they know goes beyond anyone's expectation.

I was the one who created them all.

From Celestia and Luna, to the ones who record the story Observer and Keeper.

So many lives and destinies across hundreds of universes, all showing that no matter what could happen, destiny is always fixed, except for one creature.

Sunset was born without a destiny and across the multiverse she has taken many roles; from mentor to guardian, from nightmare to savior. This is her curse and blessing at the same time.

From the scientific bases in Phobos and Deimos, to the frozen mountains of Skyrim. She is a protector of Konohagakure, a fighter wearing the sacred Cloth of the Phoenix, she is the Avatar, she is a singer known as Jem and many, many more adventures.

All of that is found inside this multiverse.

But a darkness that infects all is aproaching and will soon strike with only a few beings aware of the danger he represents to existance in general.

And what's this about a mysterious guest and a tea party?

Chapters (195)