• Published 15th Nov 2013
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Cheerilee's Thousand - xjuggernaughtx



Cheerilee goes on one thousand terrible dates.

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Date Thirty-Seven - Savings and Groan

Cheerilee’s jaw sagged open when she stepped out of the cab. The residence beyond the wrought-iron gate could only be described as opulent. Expertly cropped topiary dotted the acreage, framing a massive marble fountain. Beyond it was an estate that made Filthy Rich’s look like a summer bungalow. No wonder he asked for formal attire.

Curling her hoof around an iron chain, Cheerilee pulled. For a moment, nothing happened, and then her ears perked up. From somewhere deep within the estate, a muted tone rolled out across the grounds. The three-note sequence seemed to come from everywhere at once.

“I suppose you have an appointment, miss?”

Cheerilee jumped back, her heart hammering wildly. The tuxedo-clad pony had appeared so suddenly that he may as well have materialized out of thin air. She took a few deep breaths and leaned against the gate. “I, um… hi.” she said.

The butler arched an eyebrow, but said nothing.

Cheerilee swallowed hard. “Uh, yes. I’m expected. You see—”

“Spats, quit being such a fuddy-duddy and open the gate for our guest!” a handsomely jacketed unicorn called as he rounded the fountain. He smiled at Cheerilee as he trotted over.

The butler’s eyes travelled the length of teacher’s dress and his lip curled in the smallest of sneers. “I’m sorry, sir. I thought she must be collecting for something. I know how you—”

“Thank you, Spats,” the stallion said, his voice taking a slight edge. “That will be all.”

The butler turned and bowed. “Very good, sir." After pulling his tuxedo jacket back into perfect alignment, Spats trotted back to the mansion.

“I’m sorry about that,” the stallion said, a wry grin sliding up the right side of his copper muzzle. “Spats is terrific at his job, but he’s got these old-fashioned views of wealth and what it means.”

“Oh, that’s all right, Penny," Cheerilee waved her hoof at the estate. “But when you told me that you were financially secure, I wasn’t… I didn’t..." She twirled her hoof while searching for the right words. Everything was so amazing that she hardly knew what to ask about first.

Penny Pincher laughed. Reaching up, he slid back a massive bolt and opened the gate. “Trust me, when you’re in my tax bracket, the last thing you want to do is get into a conversation about bits. It stirs up all kinds of trouble." Stepping outside, he closed the gate behind him.

Cheerilee smirked and rolled her eyes. “Well, I’m not in any danger of that. I love teaching, but nopony ever got rich off of what I make.”

“Nonsense!" Penny Pincher smiled, but his eyes hardened. “It’s not about how much you make, it’s how much you save! I used to repair tractors, and now...” He swept a hoof before them, highlighting his vast acreage. “But enough talk about such sordid things. We’ve got a celebration to attend! Do you know Cracked Wheat?”

Cheerilee frowned and put a hoof to her chin. “That name sounds familiar.”

“Do you spend much time in Buckland?”

Cheerilee’s ears perked up. “Oh, he’s their baker, right?”

Penny nodded. “Yeah, and he’s throwing a party today for his uncle. I thought we’d drop in.”

“Well, that sounds lovely. When do we leave?”

“Well, now, I suppose,” Penny said, taking a few steps. “No time like the present.”

Cheerilee took a few hesitant steps after the unicorn. “Is it a garden party? It’s awfully early, don’t you think?”

“Oh, it doesn’t start until later today,” Penny said, shrugging, “but it’s a long walk.”

Cheerilee rocked back on her hooves. “Walk? It’s fifteen miles to Buckland! Shouldn’t we send for a cab or something? If I’d known, I would have held mine.”

Penny Pincher snorted, shaking his head. “Why spend the money?” He gave the mare a sunny smile. “Besides, exercise is healthy, don’t you think?”

Glancing down at the satin-lined hem of her dress, Cheerilee frowned. It was covered in road dust and they’d barely begun the journey. “Are you pulling my leg?”

“I make it a point to never lie,” Penny said, suddenly becoming serious. “Especially when pretty mares are involved.” Rearing, he took off like a shot. “Come on! I’ll race you!”

“Wait! Come back!” Cheerilee charged after him, wincing as her hoof came down on the bottom of her dress.

~~~

Cheerilee shook the torn hem of her gown under Penny’s nose. “What were you thinking?” she said, pointing to the stained fabric. Completely covered in mud, it was ruined.

“Calm down, calm down,” Penny said, holding his hooves up placatingly. “I’ve got it all worked out.” The air around the two of them hummed with power as the unicorn’s horn glowed. Cheerilee watched as the grime was magically scoured from her dress and the hem’s trailing threads re-knit themselves. “I taught myself how to maintain clothes years ago. It saves on expenses.”

“Well, I…” Cheerilee eyes traveled a circuit between her repaired dress, Penny’s smile, and her own hooves. “It’s, um, well… You could have warned me!”

Penny dropped his gaze, nodding. “I’m sorry. You’re right. I, uh…” He licked his lips nervously. “I didn’t think.” He tilted his head, looking up at her. “Will you forgive me?”

Cheerilee let out an exasperated sigh. It was so hard to tell if Penny was being sincere or playing with her. “Okay, okay,” she said. “Just… no more surprises like that.”

Penny bowed his head slightly. “I wouldn’t dream of it.” He offered the mare his leg. “Shall we?”

Cheerilee hesitated a moment before hooking his leg with her own. She was still a little miffed, not to mention out of breath, from all the running. Cheerilee inhaled deeply and forced herself to relax as he gave her that crooked smile again. It was so… so roguish for such practical pony. Like the dashing ne-er-do-wells from the covers of Rarity’s romance novels.

The mare was pulled out of her daydream when Penny Pincher pulled up short.

“What?” she said, after a moment.

Penny’s eyes travelled slowly back and forth as he frowned. “You… didn’t happen to bring anything with you, did you?”

Cheerilee’s brow furrowed. “Bring something? Like what?”

Penny scratched his mane. “Well, you know, like flowers or a small gift. Something like that.”

Cheerilee frowned. Her temples were beginning to lightly pound, and that only happened when things were unraveling. “Why would I do that?” she asked, keeping her voice carefully neutral. “I don’t even know these ponies.”

“Oh, no reason you should have. I was just wondering,” Penny said. “Don’t worry, I think I have it covered, anyway.”

The pounding ratched up a notch. “Penny, what exactly—”

“Pardon us!”

Cheerilee and Penny jumped out of the way as a carriage rumbled by and disappeared around a bend.

“Ah, good!” Penny said, smiling. “We must be almost there. Come on!” He took off again, only to backpedal. Looking over his shoulder, his eyes twinkled. “Don’t worry, I’ll fix your dress right up if it gets dirty again.”

~~~

Rounding the bend, they arrived at a massive stone church surrounded by a sprawling cemetery. Dozens of ponies milled around the entrance, clustered in solemn groups. Cheerilee shot the stallion a confused glance. “His party’s in a church?”

“Yeah, I don’t get it, either,” Penny said, shrugging. “I’d just have it at home, but ponies have weird taste, sometimes. Look, you go on inside, and I’ll meet you in a few minutes. I’ve got to take care of the gift.”

“What? I don’t know anypony!”

Penny patted her on the back. “Cheerilee, you don’t give yourself enough credit. You just don’t know how charming you are. They’ll be eating out of the sole of your hoof in no time!” He nodded to a well-dressed pony as she opened the church’s large oaken door. “Just be yourself, and I’ll be there before you know it.”

Cheerilee’s hooves skittered across the polished stone floor, she was swept inside by a tide of grim-faced ponies. Her head was really beginning to hurt at this point. Okay, that stallion is going to be answering some serious questions when he gets back, she thought. Trotting off to a sparsely populated corner of the church’s narthex, she tried to avoid making eye contact.

“It’s so nice of you to come!”

Cheerilee slowly turned her head. A mare in a black veil was making her way over, dabbing at her eye with a handkerchief. “Err…”

“This turn out…” The mare stopped, her voice catching. “It’s overwhelming.”

Cheerilee’s eyes travelled slowly around the room, and her heart sank. Black, black and more black, she thought. She looked down at her own dress. Black, but just by chance. She still hadn’t returned it to her sister after the disastrous date at the symphony. She looked up to find the mare staring at her, tears swimming in her eyes. “I, uh…”

“There you are, Cheerilee!” Penny made his way over, carrying two large bouquets.

The mare wiped a tear as it fell. “Oh, everypony’s so thoughtful! Bunt would have been so happy to see this!”

“There, there,” Penny said, gently placing the flowers into the mare’s hooves. “He was greatly respected.” Penny rubbed the mare’s back as she sobbed against him. Catching Cheerilee’s eye, he shrugged and gave her his crooked smile again. “Ma’am, we’re going to go sign the book.”

The mare tried to reply, but ended up just nodding as her voice failed her again. She carried the massive bouquets through a set of double doors, disappearing into the nave.

“Close one,” Penny said, hooking Cheerilee’s leg again. “Come on, let’s—huh?”

Cheerilee gave the stallion her frostiest stare. “You’ve got about ten seconds to explain why you’ve brought me to a funeral, buster.”

Penny’s face wrinkled in confusion, then cleared. “Funeral? No. Look, you don’t understand. Let me show you something.”

This had better be amazing, Cheerilee thought as she reluctantly allowed herself to be pulled further into the church.

Penny pointed down the wide center aisle, hopping from hoof to hoof. “Look. Look!” he whispered to her. “They’ve got all the food and punch you could want!”

Cheerilee’s mouth dropped open. Clustered around an open casket was a three-tiered assortment of various grains and vegetables with an assortment of spreadable cheeses. Off to one side was an enormous crystal bowl with a ladle.

Cheerilee whirled, advancing on Penny Pincher. “Have. You. Completely. Lost. Your. Mind?!” she hissed. “You said this wasn’t a funeral!”

Penny threw a hoof out beside him. “It’s not a funeral! It’s a wake!”

Cheerilee bared her teeth. “You said we were going to a party!”

“A wake is a party!” he said, backing up. “Come on, Cheerilee! It’s got everything you could want! All mares like a good dinner and some quality conversation.”

“The conversation doesn’t usually include sobbing and dinner isn’t usually served over a corpse!”

Penny winced as his rump hit the wall. “Well, sometimes you just have to get creative to show a mare a good time at a good price! A bit saved is a bit earned after all. This is a real value, dinner and entertainment for the price of a few flowers? That’s a bargain!”

Cheerilee poked her hoof into the unicorn’s chest. “And just where did get—” Her eyes flicked to the window, and the graveyard beyond it. “Oh, no. You didn’t...”

Penny scowled at the cemetary. “Well, they weren’t using them anymore. It seems like such an awful waste.”

Several startled clusters of ponies jumped out of Cheerilee’s path as she marched for the door. “Good-bye, Penny,” Cheerilee spat, fuming. “Don’t bother trying to get ahold of me in the future.”

Penny grabbed her leg. “Wait, you can’t just leave! We just got here!”

Cheerilee shook his hoof off, then pointed to the casket. “You want some pony who won’t walk out on you? Try that guy.”

Author's Note:

A big thank you to Seether00, who gave me the idea for this chapter.

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