Why won't everypony leave Cheerilee alone about being single?!

(Featured on EqD.)

(Audio versions by Mr Kenyon and FarnesyFudge.)

One night, on Hearth's Warming, Diamond Tiara returned to her hometown of Ponyville.

She'd hoped that some things might have changed.

She didn't expect somepony to change so much.

Part of the Jinglemas 2019 collaboration.
Written for LIGHTNINGinTHEdark, who requested a story about Diamond Tiara and Cheerilee.
Edited by Anon Y Mousse, Present Perfect, Cold in Gardez and Regidar.
Big thanks to Ara for the cover art.

Cheerilee has, by and large, been detached from the events at the School of Friendship. She heard the rumors about a total meltdown at the school, and even worse ones about a diplomatic incident that followed, but by and large, she's simply wished Twilight well and went about her business of helping all the young ponies of Ponyville grow.

Then, one day, not too long after the School of Friendship reopened, a new young mind flies into her life.

Special thanks to Cynewulf and Skeeter for giving this story a once over and assuring my stress addled brain that it wasn't total garbage, and to Jack of a Few Trades, for whom the story was written, and whose own work served as an inspiration.

Written for Jinglemas 2018.

Cheerilee knows two things: she's an earth pony and she loves being a teacher at Ponyville Elementary. Nevermind the fact her mother was a pegasus and both her father and older brother are unicorns, the latter of whom just got married to an earth pony with a better teaching job than Cheerilee. It doesn't bother her, because she just loves being unable to find a higher paying job than what she has now. Really. She isn't that serious when she absentmindedly wonders if being a unicorn would improve her job prospects.

So with all that in mind, she isn't happy at all when she wakes up to discover she has spontaneously turned into a pegasus, a change that goes far deeper than just sticking wings on her back. And the trials she has to go through as a result of her new status will make her call into question just who she is and what she really wants out of life.

Rated Teen for references to alcohol and minor sexual humor.

Credit for the Cheerilee vector used for the cover image goes to J-Brony

*Featured 7/18/14 and 7/19/14*

It was only a few days ago when I lost my voice and Fluttershy had to sing in my place with the Ponytones. Then, just the other mornin', Rarity's asked me out to a big fancy dinner in downtown Ponyville. What could this mean? Have I done somethin' wrong? Is she finally kickin' me out of the quartet? Or, even worse, could an elegant unicorn like that actually be interested in a stallion like me?

I ain't no good at reading ponies, and I'm even worse at speakin' my thoughts out loud. Rarity is a nice, elegant lady, and I'd be a plum fool to hurt her feelings. Still, the truth's gotta come out somehow. There's only one mare in this-here town who strikes my fancy, and it ain't her.

Based on an idea given to me by Propmaster.

Filthy Rich is good at a lot of things...
Investments.
Trades.
Stocks.

He always considered himself to be a good parent as well.
But when Miss Cheerilee requests a meeting with him, he may have to face the fact that his darling daughter isn't as perfect as she seems.

Featured 3/16/14 - 3/19/14

Twist has been waiting for something for a long long time. Now, it appears that that day has finally come, and the little filly can barely contain herself throughout the school day.

Fair or not, most classes have that one perfect student, that one little flower that the teacher can't help but adore. Cheerilee's class is no different.

Lengthened version of the third-place winner in /fic/'s first minific write-off, "What Lies Beneath."

Featured on Equestria Daily!

Thanks to Uma for critique and cover art.

A Cutie Mark is meant to represent the personality and special talent of each pony that has one. Cheerilee's flowers symbolize her desire to help her students bloom, and the smiles represent the cheer that she hopes to bring to their lives.

At least...that's what she tells everypony who asks.

[SEMI-SAD]

It's the end of the week and Cheerilee is enjoying a drink at the bar. Her mellow mood is soon disrupted. The seat next to her is taken by none other than Princess Luna, who has her own drama to unload on anypony who will listen. Or understand her...

Rated Teen for drinking and adult situations
Cover art by me.

Reading by McClain Media.
Featured in an article on Equestria Daily on 12/21/2022.