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.”
Dearly beloved.... and sponges. We are gathered here together for the buffet....
4379827 There is just nothing like stuffing yourself next to the stiff.
Penny Pincher is doing this all wrong.
What you do is invite mares from OUT of town to Ponyville and then suggest a walk through a widely trafficked area.
BOOM! Free Pinkie party in 3... 2...
4379851 Extra sprinkles happen if you sigh a lot and look glum.
I'm shipping Cheerilee and caramel now ._.
Love this fic man xD
This guy's a piece of work. He has a mansion, yet he lives like a homeless bum just so that he doesn't have to loosen his purse strings. There's a fine line between being frugal and being cheap, and he sailed right over it into new territory: Being a complete moron.
4379980 Thanks! I'm glad it's entertaining you!
4380022 He's just dedicated to being economical. Really, really, really dedicated…
I thought I had Penny Pincher figured out just by the name, then the mention of black came, and I knew what was going to go down.
Have I told you that I love you?
4379827
Then come on down to Vinnie's crematorium and brick-oven pizzeria. Cuz grieving is hungry business.
Ashes to ashes
Crust to crust
4380369 I'd hoped this one would meet with your approval!
4380049 Yet the creeping horror of the terrible date kept advancing. You screamed, "No! No! I cannot bear witness to this unnatural terror!" Still, the date came. Your knowledge bought you no time. Your wisdom did not blunt the terrible reality that is Cheerilee's love life. Like a lurking tiger. Like a cruising shark. Like the unstoppable, unavoidable hurricane, it came for you.
You will never be the same...
4367176 What killed the dinosaurs? THE ICE AGE!
Oh god.
That end line...
Just, yessssssss.
~Skeeter The Lurker
At least he didn't try to pick her up at the funeral... that would have been so Will Ferrell.
If this does reach 1,000 chapters, think Cheerilee will take up abstinence at the finale?
4380704 Only if I want to be lynched. I think if this does reach that milestone, I'd better actually ship her with somepony or the pitchforks will seriously come out for me.
4380736
Don't worry, I'll protect ya if it ever comes to that.
This was excellent, as always. Keep up the great work!
4380796 Thanks! It's always nice to know when people like this stuff. It keeps me going, especially when I'm wondering if a chapter is going to work, as I was for this one.
Penny looked away, scowling. “Well, they weren’t using them anymore. It seems like such an awful waste.”
Did he....
That JERKE!!!!!!
Haha, I didn't see it coming! I thought he might have been stealing, but oh, this is kinda worse.
Liking that last line too.
Penny Pincher still seemed like an okay guy up until the funeral part. Heck, he didn't sound so bad compared to the other ponies Cheerilee dated until the taking flowers from graves part. I don't understand why he keeps a butler if he's so insistent on not even taking a cab, but I'm thinking Spats insists on staying himself.
You have to be careful. Write something any more funnier than this and I just might die from laughter.
He took a date to a wake?!? Okay, put this guy on the 'asocial weirdo' list.
You said you were having trouble making them unsympathetic?
Well, this guy was an utter tool, so you have succeeded quite effectively in that. It was a pretty funny twist, too.
Wow, even for this story that was an appalling date. I was staring at the screen in jaw dropping horror by the end.
4380573 When Cheerilee is done putting up with shit, she's done.
4380581 I should just transition right into another date as some mourner picks her up. Cheerilee never gets a break.
4382570 You know, the answer to "Did Cheerilee's date just..." is almost always yes.
4382629 He just has ingrained habits. He's wealthy, but he got that way through scrounging. Now, he can't help but to scrounge. He doesn't even think about it, but he lives a wealthy lifestyle. Butlers are part of that.
4382687 We who bring you Cheerilee's Thousand would like to remind you that you read at your own risk. We are not responsible for any ruptured internal organs or beverages erupting from your nose.
4382867 Well, in his defense, they did have spreadable cheeses. Who can resist that?
4383598
Oh, you think that, but:
Someone always likes these dudes! Still, I really wanted to make this guy reprehensible, so I ramped up his niceness at the beginning and chipped away at it until I thought he was really vile. I'm happy with the way this guy turned out.
4384180
Yep
How could I forget!
4383632 Mission accomplished! I'm glad people haven't become too jaded to Cheerilee's fate yet. I'll be sad when people aren't affected anymore.
4384168
Good on her.
~Skeeter The Lurker
It would have been more impressive to actually spend money on their date.
Considering his life style, it would have meant a lot.
having just read the whole story, I think its safe to say that Caramel is somehow winning.
Poor, poor Cheerilee - I almost feel bad for laughing (almost)
4382570 This comment keeps cracking me up any time I see it!
4387446 This is a slowly forming universe of terribleness for Cheerilee. As we move further into it, she'll be like the eye of a hurricane. A twisting vortex of terrible dates that spans the breadth of all Equestria! The continuity of these failures breed new opportunities, which will feed yet more.
4387740 Well, he's chalked up the most abuse. I guess that's a win. Sort of.
4389139
That's what I'm here for, dear sir. Entertainment!
4379980
You cad! Cheerilight 4EVER!
I'm still waiting on the date with Tirek.
4390808
That could actually work. Even though the hearts and hooves episode aired just a couple of weeks before 'it's about time' it has often been theorized that the episodes arent shown in chronological order.
Ergo, an escaped but incredibly weakened Tirek could hypothetically be a date for Cherilee.
And I cant help but see him as an eccentric but endearing gentleman, right up until he tries to eat her magic.
Favorite part of the entire thing. Oh my goodness... ... I fully understand Cheerliee's position.
4391421 Ah but that wouldn't be a problem. Cheerilee is an earth pony, and Tirek needs to consume unicorn magic before he can consume the magic of pegasi or earth ponies.
LOLOLOLOL I laughed so hard at this. Penny Pincher is so awesome!!!!! This is literally the best chapter of fanfiction that I've ever read.
This one was a riot, albeit a tad more predictable than the others. Many of these good stallions have qualities which turn into infuriating vices. Penny Pincher is no exception
Two minor grammatical error:
The mare tried to replied, but ended up just nodding as her voice failed her again.
Should be reply.
and
Several started clusters of ponies jumped out of Cheerilee’s path as she marched for the door.
Should be startled.
And another possible error:
“Don’t bother to get ahold of me in the future.”
Might be better written as "Don't bother trying" . . .
Peace
4752862 Whoa. How did I miss this comment for so long? Thanks for the edits!