The same old Cheerilee, in the same old classroom, looked out onto the same old playground and saw what were essentially the same old foals rushing around. The bully shouting. The manic running around. The quiet one. The nutcase scribbling furiously.
In their midst, Captain Pip, pirate of the five seas, on forays to strange lands after rare treasures.
Cheerilee sighed and returned to the same old desk. Since no one was around…
She took out an old framed photograph. Her, and five fillies from her school days. Fruitbasket. Honey Drop. Cotton Top. Blueberry Swirl. And Rarity.
Her brow hardened. So Captain Cheerilee she’d be.
As soon as the foals poured in, she put on her best smile. The Five used to love her smile. She wouldn’t abandon them.
During those summer holidays, Captain Cheerilee set sail. Set a course for pony number one: Fruitbasket! Town of Tall Tale.
Fruitbasket was a safe bet. Used to be the quiet one. She’d never been the adventurous type…
Wait, what!?
Cheerilee hurried back. Examined the poster.
Went inside the Pineapple Palace.
Fruitbasket!? Exotic dancer!?
Right there on the stage. Still using the kicks and turns Cheerilee had taught her long ago!
Cheerilee asked around. Fruitbasket: the most beloved mare in town. Exotic, exciting, and endlessly pursued: stallions tried to climb onto the stage.
Burning inside, Cheerilee fled.
Once again, Captain Cheerilee set sail! Pony number two: Honey Drop. Manehattan.
Honey Drop was their nutcase, drawing impossible contraptions. Ashamed for thinking it, Cheerilee suspected such a nutcase wouldn’t possibly become famous.
Hungry, Cheerilee went to a diner.
Pancakes? Pancakes, please.
With honey? Please.
Honey Drop’s finest?
A pause.
Honey Drop’s…?
Cheerilee asked around, ran, found the Tower of Honey: a hexagonal prism. Rushed inside.
Honey Drops. A room filled with beehives. A factory, taking and replacing slots of beehive, filling jars.
“My patented Honey-o-Matic Machine!” Honey Drops shook her by the hoof. “You told me to believe in myself, Cheerilee! And here I am!”
Cheerilee wore the smile for as long as she could.
Wearily, Captain Cheerilee braved stormy seas. Someone had to be in the same boat as her. A backwater schoolmarm, not a superstar dancer, honey emperor, dressmaker extraordinaire! Perhaps pony number three: Cotton Top!
And pony number four, it turned out. Groaning, Captain Cheerilee learned about Cotton Top and Blueberry Swirl. Canterlot Celebrities.
Defeated, Cheerilee arrived. Still, for the sake of old friends, she had to reconnect. It had been too long. Their old days had been her best days, when she could shout and scream at the world and spit on the idea of being respectable.
Years ago, all of them had formed a band. The Cheerilee Five were once singers! They’d started the Rockin’ Beat. They’d given the movement its philosophy. Their philosophy. They’d told the world – the stuffy, traditionalist, old-mare’s world – that they were free!
She attended this concert this night, more out of duty than anything else.
Blueberry Swirl, shouting orders on the stage. She’d always been a bully. Cotton Top rushing about with costumes. Always the manic one.
Then the show started.
The new band were magnificent.
And she? Stuffy, traditionalist, old mare.
She left.
The same old Cheerilee, in the same old classroom, looked out onto the same old playground and saw Captain Pip. Oh yes, he’d rally them today. And tomorrow, he’d be an accountant, or something, while they went on to have amazing adventures instead.
Cheerilee forced her smile when they came in. She went through another forgettable lesson.
Eventually, all the foals left. She ventured outside, trying to look on the bright side. At least her students loved her. She had a cosy town with good neighbours. She had her health.
She had…
Five friends, waiting on the path.
Fruitbasket. Honey Drop. Cotton Top. Blueberry Swirl.
And Rarity.
All there. All beaming at her. All reaching forwards for a group hug she wasn’t remotely prepared for, but which took her back.
But how? Why?
They’d liked seeing her again. She’d always inspired them, loved them, pushed them up to be more than they thought they’d ever be. To see her come looking for them had made them realize what they were missing.
They made her Captain Cheerilee again. They asked her where to? Old Sugar Cube corner? For old time’s sake?
Stunned, but smiling for real this time, Cheerilee forced herself not to cry. She had to hide the pain she’d felt. Shame on her for feeling it!
For now, she’d pretend. For them.
Captain Cheerilee’s crew set a course: Ponyville. Cradle of their youth.