Act 1: Back in the Game
Cheerilee liked to think she was in pretty good physical shape. She was a teacher, yes, but she went jogging every day after classes were over. Okay… every other day. Or a few times a week. Alright, whenever she felt like it and her flanks looked too big in the mirror. Point was, she thought she was exercising plenty. In a small town like Ponyville, she got plenty of it just going to and from home anyway. But small towns lacked certain things that a small town mare would never get used to. Like crowded streets, crosswalks, taxis… and the most evil thing in all of the universe, the true blight upon equine kind that hid in the Crystal Empire.
Stairs. Flight upon flight of stairs in each and every building.
As Cheerilee huffed and puffed and panted and dragged her hooves up the hotel’s main staircase, she was both grateful that skyscrapers hadn’t been invented before the Empire vanished a millennium ago, and cursing architects and engineers long dead for not inventing the elevator a thousand years sooner.
When she finally reached the right floor, she took a minute or eight to catch her breath before straightening her mane and continuing her journey. She muttered under her breath as she trotted, rehearsing what she was going to say as she so often had to do before parent-teacher conferences.
“Miss Harshwhinny, I just came to say I am so, so sorry for my students’ behavior,” she practiced. “I know how much you must hate sore losers, and Diamond and Silver… no, no, can’t outright blame the kids.” She sighed. “Diamond and Silver aren’t normally so bratty… no, not bratty… ill-tempered, and… no, no, I can’t tell a lie that big.”
Her ears perked up as an idea occurred to her and she cleared her throat to start again. “Miss Harshwhinny, I just came to say I am so, so sorry for my students’ behaviors. You know how rich kids can be, and there’s only so much I can do in the classroom. Still, they’re my responsibility, so how about I make it up to you?” She nodded and smiled. “Yes, I’ll go with something like that.”
She silently counted the door numbers before she reached her target. Sitting in front of the door and clearing her throat, she knocked on the door. “Excuse me, Miss Harshwhinny?” she called.
“Just a moment!” an increasingly familiar high-class voice called back. Less than a minute later, the lock clicked and the door swung open.
“Good afternoon, Miss Hhhh…” Her voice trailed off. Before her was definitely the games judge, but she was… different. Judging from the faint feel of steam coming from the room, the mare had just stepped out of the shower. Water clung to her fur and mane, both still damp. Her coat glistened slightly from the crystal windows of her hotel room, and her mane laid flat and somewhat seductively over one eye as she dried it with a towel. “…hubba hubba.”
Harshwhinny raised the brow of one of her perpetually exhausted eyes. “Pardon?”
Cheerilee quickly collected her composure before it dropped so hard it drilled holes in the floor. “Miss Harshwhinny! Yes, I was just here to apologize for the behavior of my students earlier. I-”
“No, it’s quite alright,” Harshwhinny shrugged off with a wave of her free foreleg. “I know the type. Mr. Rich is one of the sponsors of the Equestria Games, so I know what kind of daughter he’s raised. I was fully expecting her and her little friend to be outraged and make demands when the other judges and I made our decision.”
“R-really?” Cheerilee stuttered. “Well, that makes sense. I’m glad that-”
“If you’re about to give me an opinion about my judging, I’d rather you didn’t. I don’t need accusations of backroom deals or my decisions being swayed in some manner,” Harshwhinny warned.
“Oh, I’d never dream of picking favorites among my students!” Cheerilee assured hastily. “I was just saying that I was glad that it didn’t bother you too much. Foals can sometimes be a real handful.”
Harshwhinny smiled and chuckled, a sight that took Cheerilee by surprise. “I know. I have a son, myself, and he can be quite rowdy.”
Cheerilee’s eyebrow rose. “No offense, but aren’t you… well, Miss Harshwhinny?”
“I am,” she said with a slightly wary look. “Is that an issue, Missus…?”
“Miss Cheerilee,” she corrected, ears lowered. “And no, it isn’t an issue. Sorry if I offended you.”
“No offense taken,” Harshwhinny said. Her mane dried, she slung her towel across her shoulders. “Now, if that was all you had to say, I really should continue getting cleaned up. For the frozen north, it’s strangely warm here in the Crystal Empire, and sitting in the sun for hours does no favors for a mare’s coat.”
“Um, actually, I was planning to offer you a drink to make up for earlier. My treat! It’s the least I can do,” Cheerilee explained with a smile.
“I could go for a stiff drink right about now,” Harshwhinny admitted with a sigh. “Long day for both of us, I’m sure. Do you have a place planned?”
“I’m not really familiar with this city, so I asked Rainbow Dash for a recommendation. There’s a place called the Rose Quartz Canyon nearby that she says serves great fruit mixes,” Cheerilee said. “Down the street three blocks to the south.”
“I’ve never been to it, but I haven’t been in town terribly long myself,” Harshwhinny admitted. “Very well, I’ll take you up on that offer. How does a half hour from now sound?”
“Sounds great to me,” Cheerilee nodded. “I’ll meet you there, Miss Harshwhinny.”
“Likewise,” she nodded. She turned around, giving Cheerilee a good look at her flanks before she bumped the door shut with a rear hoof.
Cheerilee blinked, cheeks red and ears perked up, before she shook her head. “Now now, Cheerilee, calm down. You said you’d give romance a rest after the whole love poison fiasco,” she told herself as she trotted away. “After almost getting forcefully married to a stallion you’re not even that into, who wouldn’t want a break from their love life? What little love life I had before then. Okay, I had no love life before that, but still,” she admitted to herself with a huff. “Besides, I shouldn’t go after a pony just because they look kind of pretty, and I should definitely keep things professional with her, given all that’s going on. Just need to go back to my room for a cold shower, that’s all.”
That’s when Cheerilee reached the stairs again, and remembered she’d have to climb all the way back down. The curse she shouted wasn’t very professional at all.
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Cheerwhinny?!
Never thought I'd see this.
3965309
I didn't either. So I wrote it myself!
I bless this new ship. Let it sail safely.
Amen.
Also, I bet Miss Harshwhinny is in great shape. She was probably a participant in the Games before she turned to running the thing.
And so another mighty vessel is sent to sea, may it journey far and prosper.
3965513
I like it! 
Amen!
I... actually had not thought of that possibility.
3965673
...insert joke about plundering booty here.
3965673 I agree with you. That trophy could mean that she won a few competitions when she was younger, maybe gymnastics.
Intruiging!
3965833
Hmm, or maybe track?
3965960
Hope it continues to be!
Thank you!
Oh, this is going to be good...
I like how you used Diamond Tiara and Silver Spoon's off-screen shenanigans to get Cheerilee to talk to Ms. Harshwhinny. I didn't really think about it at the time, but that certainly does seem like the sort of thing that would happen right after the end of the episode. Looking forward to the next chapter.
I was excited for this when I saw it posted. Then I read it and I got even more excited. Then I realised it was not a one shot, and this is promising to be an ongoing.
I just exploded from excitement! Twice!
Looking forward to reading more of this, LD. How is it you come up with such unique and interesting ships? I suspect dark magic is involved.
3966722
Took me a little bit to come up with that set-up. And hope I don't disappoint!
Thank you!
3967961
Anyway, this will be ongoing, but fairly short. Three chapters total, though the second is already shaping up to be significantly longer than the first. We'll see how it all turns out, but feel free to toss out ideas! It might extend the length 
The dark magic of friendship, of course! Or selling a shard of my soul to Mr. Zebub, I can't remember.
he said.Also, comments from you are always a delight. Just letting ya know.
3968087
Awww, you make me blush.
You should probably make a group for that sort of purpose, you know? Like, just make a group where a bunch of people can have their stories on involving shipping two ponies that nopony's shipped yet together.
3969478
Oh my god.
3969708
Maybe. I mean, there's already the groups Unloved Couples, Underappreciated Shippings, and Uncommon Shipping Pairs, but for new, novel stuff? I don't think one exists. What would I call it, though?
3969890 Hmmm, maybe...
Oh, wow. This might be tougher than I thought. Normally, it's easy for me to blurt out stuff that makes sense.
How's about "New shipping."
Just brainstorming.
Good story, by the way.
3969890
3969894
"Maiden Voyages" in reference to the first time a ship sets sail? Could have the group used as an archive for the first story of every ship.
3970306 Actually, that one sounds much better than my idea.
Dis gon b gud. May this ship sail far and wide.
3969894 3970306
Ohhh, I like! Or perhaps Shipping Pioneers? I don't want just the first; that'd be way too restrictive. But it would be nice to have a group with all the shipping stories that are daring to be different.
3971237
Hope it is! Next chapter goes up tomorrow~!
3971244
Heck, you could have fun with it and put both together in some way, like "Maiden Voyages of the Shipping Pioneers"
And I get what you mean by only the first being too restricting. Would also be really hard to track down the original shippings (especially mane 6, for example).
Oh, I like this already. This is a unique ship, you have caught their personalities well, and I can see this situation unfolding without much trouble. I will be keeping an eye on this story.
Very unusual shipping, but I like it, and I will be keeping an eye on this story
3969478 Oh-ho-hoh! I get it!
Hmm, I see what you're doing there!
Risqué jokes indeed
Great setup BTW as others have commented. Definitely watching to see where this goes.
3971346
Only problem is that I'm not the administrative type. 
Even better!
3972238 3973152
Glad you liked it; hope I don't disappoint!
3974131
I was wondering when someone would get that!
3974131
3974878
What?
I don't get it. 