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



Cheerilee goes on one thousand terrible dates.

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Date Fifty-Three - Join the Horde!

Apple Bloom’s lip curled into a tiny snarl, and she pawed at the cobblestone street with her hoof. “Back off! Don’t y’all come no closer than that!”

A few yards away, Lily and Meadowsweet blinked several times before crossing to the other side of the road. They shot bewildered glances over their shoulders as they trotted away.

“That’s right! You just keep walkin’!” Apple Bloom bellowed after them, making sure to catch as many eyes as she could in the process. Ponyville’s market district was still full of last minute shoppers, and each one carried with them the potential for disaster.

Red-faced, Caramel’s lips twitched into what was probably an attempt at a rueful grin. When Cheerilee widened her eyes and took a careful step away, he turned the failed expression onto his cousin instead. “Applejack—”

“Yeah, I’m on it.” Applejack bit down on Apple Bloom’s tail and yanked her back a few steps. “Simmer down, sis. We’re just here to run interference, not scare ponies into next Tuesday.”

Caramel squeezed his eyes closed and sighed. “I already told you! We don’t need an escort! We’re perfectly—”

“Now, now, Caramel, don’t be like that,” Granny Smith said from somewhere behind them. Even at the agonizingly slow pace they’d adopted for her, she was constantly falling behind. What was normally a ten minute walk through Ponyville to the lake had taken nearly forty-five, and they were only halfway there. “Didn’t I hear you belly-achin’ half the day away yesterday about your lonely heart? If you’re so fixed on heatin’ things up with this here filly, then help from your kin’s the surest way.”

Cheerilee’s mouth curled up into the smallest of smirks. “‘Heating things up with this here filly’, huh?”

Caramel swallowed, his cheeks now flaming red. “Well… I-I didn’t exactly say it like—”

“Oh, don’t be so bashful, cuz!” Applejack winked at him, then bumped him hard with her hip. When he stumbled up against Cheerilee, Applejack pinned him in on the other side. “You’re always sayin’ that you ain’t got no experience with mares, so—”

“I didn’t say no experience!” Caramel shot back with a glare. “I said—”

Applejack raised her voice. “—so the family’s here to make sure things runs real smooth for the two of you tonight.”

Cheerilee jumped when Big Mac said “Eeyup” from somewhere off in the shadows. Applejack had sent him east to scout for potential danger when they’d crossed into town, and Cheerilee had completely forgotten he was around.

Caramel groaned. “This can’t be happening. It’s got to be a nightmare.”

“Oh, I don’t know,” Cheerilee said quietly, elbowing Caramel in the ribs. “It’s kind of cute in a clingy, slightly crazy sort of way.”

“That’s right! You two get to talkin’!” Granny Smith trotted marginally faster in a vain attempt to catch up. Failing, she compensated for the distance by yelling at full volume. “Now, Caramel, try puttin’ your hoof ’round her shoulders, and if’n she’s inclined, maybe grab a little bit more if you can get it! Not too fast, though! You can’t put a bun in the oven ’til you heat it up nice and proper first!”

Cheerilee stiffened for a moment. “Okay, maybe less cute now.” They were just passing Berry Punch, who had been in the process of waving, but was now so overcome with giggles that she fell into a nearby bush. Cheerilee shot the bush a dirty glance as it roared with laughter.

“Aww, don’t mind Granny, you two. She’s from a different time.” Applejack rummaged in her pack for a moment, then pulled out a small basket. Thrusting the handle into Caramel’s mouth, she pulled several items out and held them up for Cheerilee to see. “I packed y’all some snacks, and this here’s a book Twilight sent along. Your Research Facility or Mine: Ninety-Nine Scientifically Evaluated Conversation Starters for Potential Couples.” She rolled her eyes. “That pony... Anyway, Caramel, I also got you some flowers for you to give to Cheerilee. Oh, guess I shoulda mentioned those earlier. Well, here. Better late than never, I guess.”

“Thanks…” Cheerilee said as Applejack dropped the bouquet into her hoof.

Digging further, Applejack pulled out a small bag from Carousel Boutique. “And here we got edible socks, you know, if things are lookin’ that way. Rarity’s tryin’ some new—”

“Why would anypony wanna eat socks?” Apple Bloom said. Her left eyebrow arched, she looked back and forth between her sister, Caramel and Cheerilee, all of whom seemed to find Ponyville’s architecture particularly interesting all of a sudden.

“Uh… Well, I’ll tell you later, Apple Bloom,” Applejack said after an uncomfortable silence. “Anyway, if y’all need anythin’—”

“What do they taste like? Can I try ’em?” Apple Bloom leapt for the bag, but her sister pulled it away. “C’mon!”

“No!” Applejack set a hoof against her sister’s forehead and pushed. Apple Bloom’s hooves scrambled across the cobblestones as she fought to advance. “Quit it! Ain’t you supposed to be clearin’ the way, little seed?”

“Oh yeah!” Whirling, the filly snatched up a stick and charged a stallion sitting on a nearby park bench. “Hey, you! What’re you tryin’ to pull sittin’ there like that?”

Applejack smiled while the wide-eyed stallion scrambled away. “Well, it ain’t exactly subtle, but I reckon it gets the job done.”

“Eeyup.” Big Mac bounded into the light for a moment and scanned the area with narrowed eyes before leaping into a dark alley on the other side of the street. Cheerilee winced when he apparently slammed headfirst into several trash cans. Two metal lids rolled into the road to twist in lazy circles before clattering to the ground, and an ill-tempered cat shot by, hissing back the way he’d come as he ran past them.

Caramel sighed again, this time much more heavily. “Sorry about this. I’ve been trying to talk them out of this all day. I, um… I finally just told them that they could walk us to the park, but they’d have to leave after that, so it’ll just be a little while—”

“That’s right! Caramel here’s been fussin’ somethin’ fierce since noon-time yesterday.” Granny Smith held a hoof up after them, and they stopped to let her catch up. Again. “In the end, he said he wished he’d never dropped by to talk, but that darned fool says the most darned foolish things sometimes.” She fixed him with a single beady eye. “A stallion gets a certain swagger when some mare’s got him hot to trot. In my day, we called it the Foal Stroll, and Caramel’s been strollin’ for months now.” She tipped the crimson-cheeked Caramel a wink. “Don’t you fret none, young’un. Your family approves of Miss Cheerilee, so we’re stickin’ to you like glue ’til the deed’s done!”

A small crease appeared between Cheerilee’s eyes, and she frowned over her shoulder. “Look, we’ve seen each other a few times, but Caramel and I aren’t quite—”

Applejack pushed her hat back from her eyes. “Granny, don’t you think you’re layin’ it on kinda thick? There’s plenty of time for that later. Tonight’s about romance, so let’s let the lovebirds fly a little.”

“Yes. Alone.” Caramel said through clenched teeth. “See? There’s the lake. We’re here safe and sound. You can all go home now.”

Applejack sat and crossed her hooves over her chest while squinting suspiciously out at the shimmering water. “Right, so about this lake thing. The family had a little talk this mornin’, and we’re not so sure it’s a good idea. Somepony might fall in the water and catch a cold, or… or maybe trip on somethin’ since it’s gettin’ pretty dark.” She leapt back to her hooves and leaned in with a grin. “So why don’t y’all come back to the farmhouse? We got loads of games, good food, better company,” Applejack waggled her eyebrows, “and hay to roll in, if you know what I mean…”

“I wanna roll in the hay!” Apple Bloom said.

“Uh… why don’t you just jump in the hay, sis?”

Apple Bloom squinted up at her sister. “Huh? What’s the difference? I mean, of course I’m gonna jump in it first, but then—”

Applejack threw a hoof over Apple Bloom’s mouth. “So what do y’all say?”

Cheerilee squeezed the bridge of her nose as the Apple family leaned in, their smiles wide and eager. “I... appreciate that you all apparently, uh, really care about Caramel’s love life, but we’d really just like a little privacy.”

Caramel nodded vigorously.

“Thought y’all might be like that,” Applejack said with a disappointed sigh. “All right, y’all, you heard ’em. We gotta form a perimeter. Nopony gets through.”

Big Mac trotted up, a banana peel and what appeared to be tomato sauce stuck in his mane. “Eeyup!”

The four apples each took two steps in a different cardinal direction, then turned right. Faces resolute, they marched in a circle around the pair.

Cheerilee set her hooves on her hips. “This isn’t privacy!”

“Don’t you fret none. We’re all kin here.” Granny Smith’s eyes traveled up and down Cheerilee. “Well, soon enough, anyway.”

Cheerilee started when Caramel cupped her ear with his hoof. “I think we’re going to have to run for it,” he whispered. “They’re, um, well… they’re pretty serious about family.”

“You’ll probably find this surprising, but I picked up that somehow.” Cheerilee’s eyes tracked the Apples as they marched by. “So what do you think? Different directions, then meet up at my place?”

Caramel nodded. “On three. One. Two. Thr—oof!

As Caramel leapt, Big Mac’s unerring hoof swatted him out of the air. Across the circle, Applejack lassoed Cheerilee’s leg and yanked her back. The pair collided, falling into each other in a tangle of legs.

“Hoo-ey! Y’all act like we ain’t never herded before!” Applejack grinned while she looped her rope again. “Critters get this twitchy look about ’em when they’re thinkin’ about runnin’, and you two are twitchin’ like crazy.”

Caramel slapped a hoof over his face. “But—”

“No buts!” Granny Smith stomped a hoof. “Get to kissin’ so we can all go home!”

Caramel cleared his throat. “Okay, that’s—gmrf!

Applejack grabbed Caramel’s cheeks and steered his head toward Cheerilee. “He’s kinda shy. You might have to make the first move. I’ll just hold him here for you.”

“Here, let me.” Cheerilee took Caramel’s face in her hooves and pulled him close. All around her, the Apple family’s eyes widened. Turning abruptly, Cheerilee squinted at Apple Bloom flank. “Hey, is that a cutie mark?”

Apple Bloom leapt into the air, spinning so quickly that twisted into a double flip. “What? Where? What is it?”

Cheerilee snatched up Caramel’s hoof and yanked him through the opening that the distracted filly had left. “Run!”

“Hey, y’all get back here and make out!” Applejack said, fumbling for her lasso. “Don’t make me hogtie you!”

“My... place?” Cheerilee said to Caramel between ragged gasps.

Sucking in huge gulps of air, Caramel could only nod.

“Then you… go… left.”

As Caramel broke away and disappeared off into the night, Cheerilee dove into a bush and curled into the tightest ball she could manage. Seconds later, Big Mac thundered by, his face set into a deep scowl. Cheerilee waited for his hooffalls to fade away before creeping out from cover.

Applejack casually stepped out from behind a tree, swinging her lasso in slow, lazy circles. “Goin’ somewhere?”

Cheerilee screamed and leapt into air, her mane bristling out in all directions. She hit the ground running, and just managed to duck the lasso’s noose when Applejack fired it out at her.

“Granny Smith and Apple Bloom already rounded up Caramel back up, so he’ll be back here in two shakes. You’re gonna love bein’ part of the Apple family, cousin! Can I call you ‘cousin’?” Lasso whirling overhead, Applejack surged after Cheerilee. “Don’t you want a foal or twelve? I can show you how to buck apples!”

Teeth bared, Cheerilee pulled back a stout branch of a nearby tree, then released it.

“You just wait and see! The Apple family’s the best—oof!

Cheerilee fixed her eyes onto the warm glow of Ponyville and tried to remember everything that her old track coach had taught her. They say the Apple doesn’t fall fall from the tree, but hopefully that one will be laying nice and close for the next few minutes.

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