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.

There are only two ponies not joining in on Rainbow's break down. One's a stoic, so the reason is obvious. But what about the Princess of Friendship? Isn't empathy in her job description? And not a single tear.
From Season 5 Episode 5, "Tanks for the Memories."

Inspired from Crying on The Inside By Arwhale.

Yes, I know it's late. As always, your criticism and praise is welcome in equal measure. I do mention shipping, but I think you'll quite like it.
There's also a tiny bit of swearing because in my head canon Twilight would use it for the sake of hyperbole.

I have a video review! Yes, I did watch it, Yes, I know it says don't read it, and frankly you should listen to him! YouTube
Frankly I'm surprised anybody thinks this is good. As mentioned in a tiny blog blurb, I don't plan on revisiting this story because I have other terrible crap to write. I'm sorry for subjecting the internet to this.
But if you think this is bad, just be grateful I don't publish the droll I wrote in High School.

Celestia is struggling to come to terms with her true feelings for Twilight.

Unwilling to watch her sister suffer under apathy and indecision, Luna takes it upon herself to help Celestia confront her newfound feelings.

Applejack has always had a secret dream, one that some ponies would find strange for the tomboyish farmer. She's always wanted somepony to treat her to a special romantic night, while being treated like a real lady. Turns out all she had to do was have a certain rainbow-maned pegasus catch her in a dress. Such an awkward moment will lead them to a night neither will ever forget.

WINNER OF THE APPLEDASH CONTEST!

Also on Equestria Daily

Dismayed after her loss to Chrysalis, Celestia departs the royal wedding reception early, retreating to her royal chambers to console herself with a bottle of wine. Concerned for her sister, Luna soon follows to check up on her...

(Rated Teen for tipsy princesses, and thanks to Junglepony for the cover art!)

Twilight has something she needs to tell Princess Celestia--something that means a chance at getting everything she's ever wanted, or of losing everything she's ever had.

Something so terrifying that the only way she could say it was in a letter...and so wonderful that she had the courage to send it.

(Thanks to Cenit V for the cover!)

Cadance didn't know what to expect when her formerly banished Aunt Luna returned from her thousand year banishment. But, she's quite entertained by the hilarity. Especially if it means a chance to play a little joke.

Edited by Habanc. Preread by The Albinocorn, Foals Errand, and Timaeus

Cover art was done by Silfoe and used with permission! In fact, this fic is a gift for her!

Now with Spanish translation by SPANIARD KIWI.

After arriving in Canterlot, Cadence joins her Aunt Celestia for some good 'ol fun pranking Luna and Twilight, Canterlot's newest love birds. However, in the midst of their good fun, it all goes bad. Cadence ends up getting more than she bargained for.

The two ponies I care for the most, my dear sister and most faithful student, have betrayed me. My most loyal guard says I'm just being paranoid, but what would he know that I don't also? I thought the nightmare was over, but now it's clear it never went away. In fact, it's only gotten stronger and more cunning, as evidenced by how it's turning all that I hold dear against me. Well, it won't succeed, and I'll do whatever it takes to make sure of that. Mark. My. Words.

Co-Written with Razalon
Edited by Razalon
Pre-read by Razalon

The real Nightmare Moon has returned during Nightmare Night, and she plans to get revenge on Twilight Sparkle. However, she hasn't been aware of any events past her demise. Or the secret feelings a certain mare has that she's hated for over two years.