Collab with The Abyss (Chapters 1 and 2)

Proofread by Neko Majin C and edited by The Abyss (Chapters 3 onwards)

Twilight Sparkle has always ignored Hearts and Hooves Day, seeing it as just another normal day with extra chocolate and the occasional broken-hearted friend to comfort. But when Rarity convinces her that not having a date during the holiday is contrary to proper princess protocol, Twilight rushes to do everything in her power to live up to the expectations presented to her.

There’s just one problem, though: Twilight has never been on a proper date before.

After a few rather disastrous attempts to find a date in Ponyville, Twilight goes to her mentor in Canterlot in a last ditch effort in the hopes of finding the answers she seeks. Princess Celestia, however, may have something more for her than either of them had anticipated.

Twilight after witnessing the summer sun celebration as a little filly, she decides to try and get into Celestia’s academy for gifted unicorns. Opening a book with a title that was missing a single letter on it's cover, Twilight picks up a rather interesting passion while studying for the entrance exam.

That's when things start to slowly 'grow' out of control.

This is a fic based on the Time Loop Files, the format of which was first codified by Innortal on fanfiction.net.
Here's a brief guide.
The basic idea is, one character (the Anchor, usually the main character of a fictional setting) is looping back to the very first moments of their parent series every time either they die or some kind of time limit expires. They of course end up monumentally stir crazy given enough time.
Eventually others start to loop as well.
The reset is not always perfect. Sometimes a loop's history will be different to the "prime" loop, or canonical plot.
"Crossover" or "Fusion" loops also occur, randomly. These can involve the home loopers having a guest, or the anchor for one universe spending time in another, or replacements of one character by another.
Vacation Loops are where the Anchor (or others) decide/s "buck it" and lets off steam by doing whatever comes to mind. There's little or no attempt to maintain the original timeline.

In addition, and particularly more recently, it should be known that this story has a collaborative element to it - people may submit loop ideas or loops, ideally at the Spacebattles thread (a link to the current version of which is on the Trope page), and they may become included.

There's two page image options, thanks to Filraen - the current page image has been edited by the original creator from this work of theirs.. The other one is here:
http://hourglass-vectors.deviantart.com/art/MLP-Loops-466030169