The faded Maribbean Islands calendar above Stormy Skies’ scarred office desk had been stuck on April for the last several years. It hung from a single push pin, and the corners of its pages curled toward the floor. If anypony had thought to look at it recently, they might have seen that the push pin had been slowly sliding out of the wall.
But nopony had, so it came as somewhat of a shock when it fell into the firm’s fishtank. Not quite as shocking as the force with which their client had slammed their front door, but shocking all the same.
“Oh, that’s just great.” Balance Sheet rolled up the sleeve of his button up dress shirt and plunged his hoof in after the soggy calendar. Three wary goldfish peeked out from their rooms in a small underwater castle. “Like things aren’t bad enough.”
Stormy’s ancient rolling chair let out a shrill squeak as he leaned back in it. “Oh, she’ll be alright once she cools down.”
“She nearly broke our door.”
“Eh, she’s temperamental,” Stormy replied with a shrug. “Lots of mares are that way.”
Balance dropped the calendar into a wastepaper basket and scanned the sparsely furnished office for something resembling a towel. With nothing available, he sighed and wiped his hoof on his shirt. “Well, I hope they don’t have dating insurance, too, or we’ll be in deeper water than we already are!”
Stormy yawned and stretched his wings. “C’mon. It was a million to one odds. Probably good to get it out of the way. From here on out, it’s nothing but smooth sailing for this firm.”
“Smooth sailing? Stormy, this ship is sinking, and I’m the only one with a bailing pail!” Balance pulled a green binder from a nearby shelf and slammed it down in front of the pegasus. “That mare had a five thousand bit policy!” he said, pointing to an entry.
The stallions stared at each other for a long moment.
“And?” Stormy finally said.
Balance’s angry brows knotted together. “And we don’t have five thousand bits! We don’t even have five bits! Allow me to put it into laypony’s terms: We’re broke!”
Stormy waved his hoof. “She’s got to have the right paperwork first. Until then, she’s just a slightly dissatisfied policyholder.”
Balance Sheet rolled his eyes, then collapsed back into his chair. On the desk in front of him, an ever-growing tower of papers sat in his “To Be Processed” box. Just looking at them made his pulse rate spike. “It was a public display of unsanctioned magic, Stormy. Emphasis on public. There are going to be plenty of witnesses!”
“Well, until they come forth, that’s a problem for another day!” Stormy Skies opened a desk drawer and fished through it. “Hmm. Thought I had half a sandwich in here somewhere. Maybe we should get lunch. I’m starving. You hungry?”
“No, I’m not hungry! I’m about to start hyperventilating!”
“Jeez, calm down,” Stormy said, throwing Balance his stress ball. “All that tension is bad for your heart.”
“Bad for my—“ Balance glared at his partner, hardly noticing that he’d caught the stress ball and was now squeezing it for all it was worth. “You know what’s really bad for me? Terrible financial decisions! Why do we even offer dating insurance?”
“That was Hard Sell’s idea. I just ran with it.”
Balance Sheet rested his aching head on his hoof for a moment. “Why are you listening to business advice from Selly, Stormy? He didn’t win us any clients for three of his three-and-a-half years.”
“I know,” Stormy said, nodding. “I really felt for the guy, you know? He was in a rough patch, but he was really excited about getting his new product out there. Thought he could get some bites, and you can’t argue with results.”
“You call going out of business ‘results’?”
Stormy sighed and hopped off of his chair. Trotting across the room, he moved in behind Balance to massage his shoulders. “Look, trust me. It’s all going to be okay. Doesn’t it always work out?”
“A mob chased us out of Las Pegasus! And Fillydelphia!”
“And we got away! Both times!” Stormy craned his neck over his partner's shoulder to offer him his most winning grin. “That kind of thing doesn’t just happen. It’s a sign.”
Balance shrugged off Stormy’s hooves. “Well, you know what does just happen? Magical accidents! And we apparently insure against them if they occur on a date!”
“I told you, it’s a one in a million chance!” Stormy sat on Balance’s desk and leaned down to look his partner in the eyes. The enormous stack of papers wobbled threateningly. “You’ve got to be bold in this business, Bal.”
“After that mare comes back with the official report from the authorities, We aren’t going to be anything in this business!” Balance steadied his papers and slid the tray carefully away from Stormy’s twitching wings. “A rampaging monster destroyed half of Ponyville! Do you have any idea how many bits we’ve paid out in property insurance already? We can’t afford any more?”
Stormy arched an eyebrow. “Are you seriously telling me that these ponies all signed up for the optional Rampage coverage, because otherwise—”
“Yes, that’s what I’m telling you!” Balance said, leaping up from his chair. “Everypony in this town seems to think disaster is just around the corner for some reason!”
“Right! That’s what made this a great spot for insurance sales, if I do say so myself.” Stormy polished one periwinkle hoof against his chest. “They’re just begging to give those bits away!”
Balance threw a hoof out to the massive pile of paper on his desk. “Except that in this town, disaster is just around the corner! Something’s always happening! Now, on top of everything else, we have a mare whose date was transmogrified into a three story tentacle slime monster because some apprentice unicorn got a little overconfident with an unregistered tome! If the princess hadn’t have been in town visiting her student, the whole place would probably have been levelled!”
“Don’t you worry.” Stormy patted Balance on the head. “I’ve got Selly in the stacks right now looking for loopholes. We’re going to come out of this smelling like a rose.”
“Let me back up and go over this again, Stormy,” Balance said through gritted teeth. “Princess Celestia, with the help of her protege and her protege's friends, just saved the town from certain destruction. They got medals. Ponies were cheering.”
Stormy blinked. “Where are you going with this?”
“We can’t finesse this one!” A vein throbbed on Balance Sheet's forehead. “How’s it going to look when the town’s heroes trot up to the princess and tell her that we aren’t paying up? Half of them are policyholders! Why, that high-end boutique alone—”
The door at the rear of the office banged open, and through it stepped a rumpled, baggy-eyed unicorn.
Stormy rubbed his hooves together. “So, what’d you find?”
“We’re boned,” Hard Sell said. Without breaking his stride, he plucked his hat from a wall hook and stepped out the opposite door. “I quit.”
Stormy stared after him, then swallowed loudly. “Um…”
The front door flew open again. Framed by the construction site across the street, Cheerilee stood, teeth bared. “Here!” she said, waving an officially-stamped piece of parchment. “Here’s your proof that some kind of disaster happened!”
“Are you sure—“ Stormy winced at the hammering that began across the street. He cleared his throat and raised his voice. “Are you sure that what you were on would be classified as a date and not a standard social outing?”
“Yes!” Cheerilee pulled out a second document from her saddlebag. “I stood in line for five hours to get one of Princess Luna’s new permits just so I could go out last night!”
Stormy jumped a little when Balance dropped his head to the desk with a loud thud. The towering stack of papers teetered for a moment, then slowly tipped over the edge and dropped onto the floor. The breeze from the open door scattered them to the office's four corners. Head in his hooves, Balance let out a pained groan.
“Don’t mind him,” Stormy said with a wide grin. “He has a headache. Could I see that permit?”
Jaw tightly set, Cheerilee thrust it into his face.
“Ah, yes. I, um... I see.” A bead of sweat rolled down the side of Stormy’s face. “Uh, well, let me just go and get the proper form for you to fill out. I think we keep them in the, um, back room.” Stormy slid off the desk. “Say, Bal, mind giving me a hoof in there?”
Balanced lifted his head just enough to roll one eye over to where Stormy fidgeted. “Huh?”
“You know, we keep those forms in that cabinet by the rear door, and, um, I have trouble getting it open sometimes.”
Cheerilee’s eyes narrowed. “Did you know that I’m close, personal friends with Twilight Sparkle? She was a little bit puzzled when I asked if she could wait for me in the alleyway behind your business, but she’s a good sport. Be a shame if you ran into her and made her mad, don’t you think?”
Stormy swallowed again, his perspiration rolling more freely down his face. “Err, yes, but I don’t think that’s likely to happen because I’ve just remember that those forms are in my desk drawer. I-If you wouldn’t mind just taking a seat, we can get started on your claim. Now, how much did you say your policy was for?”
Balance sighed and pulled open up the third drawer on his desk. It was his special drawer. The one he kept stocked in case of emergency, and it was opening with alarming frequency these days. With a practiced ease that he’d increasingly grown to regret, he fished out a bottle of hard cider, one semi-clean highball glass, a photo of frolicking puppies, and five antacids. Setting the photo directly in front of him, he poured a liberal shot into the glass and downed it. As the bottle hit the table, his other hoof swept up the antacids, and he shotgunned them into his mouth. Still chewing, he filled the glass again, but this time to the top. Across the room, Stormy wilted beneath Cheerilee’s stony stare, but here, carefree puppies were gamboling across a meadow. It wasn’t much, but it was something. As the pounding in his temples lessened, the answer came to him. It was so easy. “Ma’am?”
Cheerilee twisted around in her chair. “Yes?”
“What if we replaced the date?”
Cheerilee looked away from him for a moment, then back. “What?”
Balance rose from his desk, a little unsteady. “I mean, what if we acknowledge that your date was ruined, but we replace the experience with one of equal or greater value? That’s what you were after, right? A nice night out?”
Cheerilee rose, staring suspiciously at the accountant. “You’re going to find me a new date? And please don’t say you’re going to try to hook me up with this shyster,” she said, pointed to where Stormy sat.
“Hey! Now that’s—”
“Zip it, Stormy,” Balance growled. He motioned for Cheerilee to take a seat across from him. “Look, with all the damage outside, our firm is in a bit of a tight spot. We’d love to pay out, but it might be years before we can.”
Cheerilee opened her mouth to protest.
Balance threw a hoof out to forestall her. “I know, I know. Trust me, we don’t like it either, but we didn’t expect half the town to get destroyed all at once.”
“You must be new here,” Cheerilee replied, her expression flat.
Balance steepled his hooves. “So you want a date, and we want to stay in business. I think we should be able to cut a deal that works for all of us.”
“And what if the next one doesn’t work out?” Cheerilee tilted her head slightly to the side and crossed her hooves over her chest. “Will I accrue interest if I have no interest?”
Balance nodded. “I think that’s fair. You are owed, and the debt holder has an obligation. It shouldn’t be too hard for us to find you a nice stallion, o-or mare, if that’s your thing.”
They shook hooves, but Cheerilee’s spreading grin shook Balance Sheet to his core. “Buddy, you have no idea.”
Those stallions are doomed. they don't know who they are dealing with.
This is how the great Equestrian Banking Economic Crisis began...
5892246 Cheerilee's misery obeys no bedtime. Even in the dead of night, the terrible dates roll on.
5892248 But they will. Oh, they will...
5892250 If Cheerilee can ever get a payout, she'll be Equestria's 1%.
Annoyed as I may be that I was left standing in that back alley for 3 hours, I got to have a wonderful conversation with Pinkie who had set up a stall selling brownies.
SOMEPONY'S BEEN IN MY MEDICINE PATCH AGAIN!
5892350 Well, if Angel wasn't selling her, um, garden on the side for extra carrot money, we wouldn't be in this situation, would we?
They should have gone broke. They're about to dig a grave to whatever the equivalent of China is.
5892450 Chineigh? Kind of a stretch...
5892370
That's because Angel knows the wall-eyed Gummy makes a great fence.
Pity that Owlouicious is narc-turnal.
5892267 She's got a better chance of that happening, than having a date that doesn't end in disaster.
Hah! I knew cherillee would start using her bad date powers for evil someday.
And thus begins the transfer of ALL OF THE BITS EVER to Cheerilee...
Hoo boy. I knew Cheerilee's dating situation was bad, but to be to the point where she has to get insurance for her bad dates? Yikes.
Also, these guys are so hosed. Even more hosed than they would've been if they just paid up instead of trying to strike this deal with Cheerilee that will no doubt end in failure.
This is amazing.
I like Balance Sheet, he's seems like a okay guy. Especially considering the stigma around his profession. Hope the date goes......well I guess we can only say we hope it doesn't go too badly by now.
5893698 Balance Sheet has a good heart, but he's a poor decision maker. I mean, he's been partnered with Stormy Skies for who knows how long. That's a cry for help.
5893663 Thanks! This one was fun to write. Nice to have new characters with a new perspective.
5892534 Twilight? Hey, Twilight! TwilightTwilightTwilight! You know what? I heard Fluttershy say that Angel said that Gummy makes a great fence. Isn't that silly? He'd be a terrible fence! Ponies would step right over him!
5892650 Think of all the disastrous gold-digging dates she'll go on once she's a member of the financial elite.
5892681 Hey, she's just going with the flow. Not her fault that Balance Sheet makes bad decisions.
Plus, don't we all owe a little something to Cheerilee at this point?
5893155 That's my favorite chapter!
5893218 I should do something more with Iron Will. His over-the-top-ness is hilarious to me.
Iron Will: "Cheerilee, those mares and stallions won't date if they can't relate. Step one on your road to romantic repair: spoil fifty dates around town. That way, everyone else will have a deeper understanding of who you are as a pony."
Cheerilee: "Let me see if I'm following you. I'm, in your mind, wholly defined by my inability to get some action?"
Iron Will: "Cheerilee, you make a motivational minotaur proud! Now look, there's Rarity and Twilight Sparkle. This is the plan: Take Iron Will's patented Bucket of Honey and throw it onto them. Next, step two: Iron Will's patented Bucket of Ants. Their hot date will evaporate!"
Cheerilee: "What? No! They're just walking. I mean, how do we even know that they're dating? I've never heard anything about them."
Iron Will: "Walking in the moonlight? They're after a fun night! Now get down there and create some emotional equivalency!"
Cheerilee: "But I can't even throw honey onto them! It's viscous. I'd have to pour it really slowly. They'd have to be standing really still."
Iron Will: "Hmm. Maybe you're right. Iron Will's patented Buckets of Honey and Ants are usually reserved for tortoises. Here's a bat. See if you can get a kneecap or two. Physical pain for emotional gain."
Cheerilee: "You're fired."
5893287 At least it'll ruin Filthy Rich. Cheerilee would like that.
5893442 It's one of the central rules to Cheerilee's Thousand. Everyone in it is either bad at their job, or so good at it that it messes up the rest of their lives. It's like Spider-Man. Peter Parker can be successful as himself or as Spider-man, but not both at the same time.
5893904 Yes but she's simultaneously slashing her own budget by bankrupting all of Equestria...
And there was a great disturbance in the Force...
Why oh why was the stallion's name Stormy Skies instead of Stormy Weather? SW would have been a much better parallel to the dire financial straits they find themselves in. (Plus, it makes for a great Marketplace reference, if you listen to US public radio:)
5894524 Actually, I listen to Marketplace everyday on my drive home. That would have been an amusing in-joke, if I'd thought about it.
I named him Stormy Skies because it gives the feeling of disaster on the horizon. Stormy Weather would achieve the same thing, but it's a little less of a standard pony name.
Heh heh, someone make a Cheerilee version of that one Condescending Wonka meme.
5896093 You mean this Ratchet? Awesome!
And now I'm imagining a Trigun-like situation where a consortium of insurance companies gets together to offer Cheerilee an exorbitantly huge salary to never go on another date in her life, just to cut down on costs overall.
5897716 Cheerilee the Stampede is Equestria's sixty billion double bit mare.
Actually, watching Stormy and Balance bumble their way through the role of the insurance girls would be pretty amusing.
5896010 Huh. Maybe I should have a follow up date with Sapphire Shores. That might be interesting...
5896522 You can in Ponyville! Well, my Ponyville, anyway. They just told the prisoners to stand quietly off to one side for a couple of weeks. How do you think Whirlwind got away?
This could yet be the rebirth of this story. Now Cheerilee has a sidekick in Balance Sheet and a totally amoral headhunter in the form of Stormy Skies, the dating game could very easily get very interesting very quickly.
5894023
I know, right, it's as if the entire economy cried out in terror and was suddenly silenced.
Gives a whole new meaning to "depression".
5905963 Probably because I really like writing the Caramel chapters. They are my favorite thing about this story, so I sort of naturally go the extra mile with them. Heaping abuse on Cheerilee is hilarious to me, and Caramel is cut from the same cloth, in my mind. He's just a hard luck pony, so dishing out a double helping of misery is two times as hilarious.
5897721
The real question is who would be Wolfwood?
Dang, Cheerilee, now that's how you figure out how to bet on Black and Red simultaneously and come out ahead either way it falls.
Nice to see the continuity with Luna's dating permits.
5934517 5921385 Considering one of the most popular ships in Trigun is Vash/Wolfwood, I imagine the insurance bros are going to have to hunt one up for her, haha! Perhaps Caramel will end up her Wolfwood, only his cross is an actual medical one full of bandages for when he inevitably ruins everything. Although the idea of Cheese Sandwich with a cross full of rubber chickens also makes me laugh and laugh. Requesting a Trigun Sandwich chapter please!! XD
This doesn't feel like it should count as a bad date since we never saw anything about the date itself. But I'm curious where this is going.