Fruitless Ventures

by Roundabout Recluse

Rating: everyone
Tags: Applejack, My Little Pony: Friendship is Magic, Comedy, Rarity, Slice of Life, Main 6
Length: 4422

Rarity discovers that Applejack has never been on a date. Clearly, this requires an intervention.

“I don’t see what’s so important about forcin’ Twi to go on dates,” Applejack cut in flatly. “She doesn’t need to date anypony. I never dated anypony, an’ I’m right content, so can you go back to readin’ that magazine already?”

Silence fell upon the table like death.

Rarity’s eye twitched.

“Oh, noooo,” Pinkie wailed, collapsing into her seat and sliding to the floor.

Twilight facehoofed.

“Applejack,” Rarity whispered, deceptively soft, an edge of danger to her tone that she’d carefully honed over the years, after many customer clashes and Blueblood-esque encounters. “You’ve never been on a date? Not even once?”

In which everypony's love life is a travesty.

Published 2024-07-08 19:30:00 UTC
Last updated 2024-07-08 19:30:00 UTC

Rarity's Completely and Entirely Generous Venture

It started at Twilight’s castle, as many things did. In fact, Rarity couldn’t think of a recent problem that had been spawned outside the castle since the last national crisis, unless she included the time when Sweetie Belle had tried to run away to Las Pegasus, but no—that was before those three villains attacked, not after.

Perhaps Trixie’d had another “incident” in the time since then. But at this point, those hardly counted.

Regardless, Twilight’s castle was often the location where tensions and startling revelations came to light. On this particular day, four of Ponyville’s resident heroes were seated around the Map as per their weekly meetup, sans their pegasus friends, who were currently in Cloudsdale for a family event.

Twilight was flipping through her non-magical mail. Lately, it had consisted of party invitations, usually with balloons attached, bills that Celestia had long stopped paying on her behalf, letters for Starlight, which Starlight always left in stacks around the castle, and junk mail. The arrival of junk mail in particular had become more frequent in the years since Twilight’s ascension, and as a result, the alicorn tended to face her mail with something less than enthusiasm.

It seemed to be Pinkie Pie’s mission to make up for that, and as such, she was rifling through Twilight’s wastebin and cheerfully sharing the contents with Rarity and Applejack, one envelope at a time.

“You don’t want a free subscription to Princesses Weekly? Oooh, what about a pamphlet for the Sponsor a Sea Creature Fund? That looks like a fun fund, doesn’t it? Fluttershy loves animals, and I love the word pamphlet, so can we keep it?”

Twilight and Applejack didn’t answer, presumably ignoring her. Rarity did not look up from the Princesses Weekly issue that had captured her interest. Scandal in the Crystal Empire? Oh, my.

“What about this one? It looks special!” A pause as Pinkie squinted at the hornwriting, then a gasp. “I didn’t know you and Prince Blueblood were pen pals!”

That drew Rarity’s full attention. “I beg your pardon?”

Twilight snatched the letter away from Pinkie and, without a glance, shredded it in a burst of magic. “We’re not, I promise. Ever since I became a princess, he’s been sending me ridiculous marriage propositions. They all go something like ‘Please marry me, I’m terribly beautiful, you have no reason to say no.’” A small snort, coupled with a shake of her head. “He’s just mad that Princess Celestia wrote him out of Philomena’s will.”

“Blueblood, that little—!” Time had hardly reduced Rarity’s resentment toward the stallion. “Isn’t there something you can do about him? Perhaps talk to Celestia or the postal service, or dissuade him through other means?”

“I guess I could, but it’s really not worth the trouble,” Twilight said with a sigh, dropping the letter scraps into a waste bin. “I’ve been dealing with him for years. And besides, do you really think I didn’t try to get rid of him? I told him every reason I’m not interested, every reason he shouldn’t be interested in me—I even told him I was already in a relationship.” She made a face. “It’s like writing to a brick wall.”

That absolute boor. If Applejack hadn’t been regarding her with an amused look, Rarity would have ground her teeth in outrage. As it was, she consoled herself with the knowledge that she was far more renowned than Blueblood would ever be. Minor royalty was no match for a famous fashion designer-slash-Element of Harmony-slash-close friend to the soon-to-be monarch of Equestria. The soon-to-be monarch who didn’t find him to be anything more than a nuisance to be shredded and trashed.

The insults felt good. Even so, discussing Blueblood made Rarity feel as though her mane would gray early, and one couldn’t have that, so she latched onto Twilight’s also-intriguing last sentence.

Later, she would decide that decision was fate.

“I don’t mean to pry, but aren’t you in a relationship? With that admirer of yours in the Royal Guard?”

Twilight’s face went red. “What? No.”

“I’d’ve reckoned it was that red-maned pony,” Applejack, idly leafing through a farming catalogue, said with a shrug. At Twilight’s frown, she added, “The one you always’re makin’ goo-goo eyes at?”

“Oooh, yeah! Sunset Shimmer!” Pinkie leaped onto the Cutie Map and shoved her face into Twilight’s.

“Um, no?” Twilight gently pushed Pinkie’s snout out of booping range. “First of all, I’m not making goo-goo eyes at her, and second—does it seem like I am?—and third, I’m not dating anypony.”

Rarity’s backup guess would have been Sunburst, although to suggest that would have incurred the wrath of an unbalanced Starlight Glimmer, no matter where she was, and nopony wanted that. Oh, well. Leaning her hooves against the Map, she posed a different question: “But for what reason?” There were plenty of eligible ponies in Equestria; Flash, Sunset, and Sunburst were but three of them. “I’m certain any number of ponies would make the first move, were you to drop even the subtlest of hints.”

Twilight shifted her wings, frowning. Rarity noted with a soft pang of envy, not for the first time, that the alicorn wouldn’t need to flirt to attract admirers. “That’s part of the problem. Ponies are interested in Princess Twilight Sparkle, just like Blueblood is, but nopony who really knows me would be interested.”

“That’s crazy!” Pinkie exclaimed in the same moment Rarity retorted, “That’s ridicu—”

“Okay, very few ponies.” Twilight held up a hoof. “But also, I’m too busy to make a relationship work. Trust me, I tried. Flash and I didn’t work out.” The faintest regret passed over her face. “And I’m only going to get busier when I take over for Princess Celestia.”

They were clearly excuses. The most inexcusable excuses to ever attempt to excuse, in Rarity’s expert opinion.

“You do have limited leisure time,” she admitted, “but look at yourself! You could easily let Spike take on more responsibilities, hire employees to manage other tasks, and go off to meet suitors at cafés at least once a week.”

“I could, but—”

“Why, I could arrange it for you! If we establish a timetable according to your schedule, I’m certain—”

“I don’t see what’s so important about forcin’ Twi to go on dates,” Applejack cut in flatly. “She doesn’t need to date anypony. I never dated anypony, an’ I’m right content, so can you go back to readin’ that magazine already?”

Silence fell upon the table like death.

Rarity’s eye twitched.

“Oh, noooo,” Pinkie wailed, collapsing into her seat and sliding to the floor.

Twilight facehoofed.

“Applejack,” Rarity whispered, deceptively soft, an edge of danger to her tone that she’d carefully honed over the years, after many customer clashes and Blueblood-esque encounters. “You’ve never been on a date? Not even once?”

Applejack finally appeared to notice the peril she’d placed herself in. She set down the Farmer’s Almanac slowly, as if resigning herself to her fate, and raised one eyebrow aloft. The brothers Flim and Flam had once urged her to patent the expression.

“Never,” she confirmed, just a bit wary, yet standing her ground. It was admirable, really. “But that ain’t a problem. I never felt like a thing was missin’ from my life, an’ you can take that to the bank.”

A strange spark shone in Rarity’s eyes. “Darling.” Her horn alit with blue, and the danger became palpable. “It’s winter. Your schedule is relatively clear, is it not?”

“Uh…”

“In that case, you have no excuse. And no possible objection, seeing as you have no personal experience that can substantiate your deeply flawed belief.”

The blue light seized Applejack’s body.

“So, as somepony well versed in the art of romance, I simply must help you see the truth.”

“We’ll start with your preferences.”

Rarity paced back and forth outside Sweet Apple Acres, bright and early in the morning, clad in a periwinkle parka and lilac knit scarf. A day had passed, as she’d needed time to compile options, and Applejack was once again detained in a blue glow; she couldn’t let her escape, after all.

“I ain’t got any dang preferences,” the earth pony deadpanned.

“Oh? That makes this all so much easier, then,” Rarity said, beaming. She unfurled her notebook with a flourish, complete with a matching quill. “Shall we begin from the top of the list, in that case?”

“Not what I meant.”

Rarity elected not to hear her. “I have it on good authority that a number of particularly charming stallions visit the Canterlot tea shoppe every Monday at three. Mares, as well. If we left now, we would have plenty of time to make ourselves presentable upon arrival.”

“Rarity, I swear to Celestia’s sun-darned heinie that I’ll kick your flank into next week if you think you can drag me all the way to Canterlot.”

“So give me some direction, darling.” The smile turned sharp. She tugged Applejack forward with her magic, just a skosh. “Would you prefer local ponies? Is that it?”

“I’d prefer to go back to my kitchen and finish cookin’ Apple Bloom’s flapjacks.”

“Are you aware that the train to Canterlot leaves at a quarter to ten?”

Applejack was silent for a long, long moment, mentally weighing pros and cons, but Rarity could feel the honesty in that silence: the battle had already been won.

Finally, with great fatigue, she let out a world-weary sigh. “We’re stayin’ local.”

“Wonderful.” With a swish of her tail, Rarity spun to face the path and commenced the trot into town, dragging her friend behind her. “A compromise, it is.”

It was all for Applejack’s own good, of course. Future-Applejack would thank her, and so would her future special somepony. And perhaps her future special somepony would be so terribly grateful, he or she would introduce her to an equally attractive friend, but that was only a possible by-product.

Applejack insisted on local ponies, so local ponies they would find.

This was how Rarity found herself camped out at a table a distance from Applejack’s own, fixing her friend with a laser-focused glare over a newspaper and a pair of sunglasses. Which were wasted in the gloomy lighting of The Hay Burger, she lamented, but such was the price of romance.

A cornflower-blue stallion sat across from Applejack. His rigid posture was a detractor, perhaps, and his continual nervous glances over at Rarity admittedly put a damper on the atmosphere, but he’d been the first gentleman to agree.

“So…” The stallion’s ears flicked. He was a good option, to be sure. Nothing noteworthy, but handsome all the same.

Applejack stared back at him with a blankness that would have made Maud Pie proud.

Rarity lowered her newspaper and plastered a cheerful smile across her face. Smile!

“I… heard you like apples,” the stallion tried.

Applejack’s brows lowered.

Oh, no. Rarity braced herself for the harsh rebuke. Like apples? LIKE apples? Partner, you an’ I’ve lived in the same darn town all our lives, and you’re saying you heard I ‘like apples’??

“Apples’re my bread and butter,” Applejack said slowly, “but I s’pose I’ve been tryin’ to branch out.”

If the restaurant had sold anything other than soda, Rarity would have choked on a drink.

The stallion brightened, preparing a response, but it was at that moment that fate chose to strike a devastating and cruel blow. Oh, poor Applejack, whose heart had just begun to open—but the entire enterprise was doomed the moment the song playing over The Hay Burger’s speakers ended, and a new one began.

Rarity’s eyes closed slowly. No. But it was too late.

“Applejack,” she interrupted, hating herself for it, “we must be going.”

Applejack’s disbelief was written across her face. “Say what now?”

A touch frantically, Rarity crossed the table and yanked her friend from her seat, shooting an apologetic glance at the blue stallion. “We must be going. Unfortunately, this date cannot continue under the present circumstances.”

“The present huh?”

“Do you hear the voice playing over this establishment’s speakers?” Though she was looking at her as though she had two heads, Applejack nodded reluctantly. “That’s a renowned romantic songwriter whom I’m sure even you have heard of. And I’m terribly sorry to say this, as I adore her dearly, but are you aware of the indisputable truth about her music?”

“Uh…” Applejack stared at the ceiling speakers, as though they held the answer. “No?”

Rarity sighed, sharing the fact with the finality it deserved: “The moment you relate to a Haybale Swift song, your relationship is over.”

Defunct. Extinguished. Fin. The end. It didn’t matter if Applejack was listening to the song or not; Rarity was, and Rarity was as much a part of this as Applejack. In a way. From a certain angle. And this was one omen that Rarity could not overcome, not when it was too late—the song was already on the second verse.

Any relationship built on this foundation was doomed to fail.

“Right,” Applejack said as she let the unicorn drag her from the restaurant. “Hey, Rarity, have you ever considered therapy?”

Long after the mares had disappeared, the stallion looked down at his burger blankly.

“…This was a date?”

A few hours later, Rarity and Applejack left the teashop and their latest attempt behind. The gray pegasus didn’t seem to mind; Applejack had bought her dessert, after all. At Rarity’s benevolent encouragement.

“Look, the mailmare’s a great pony and all, but I ain’t interested, and I get the feeling she ain’t, either,” Applejack was saying. Her ears were as flat as her glare.

“Well, you haven’t seemed interested in anyone yet, darling.” It had become quickly apparent that Applejack was not averse to making conversation, if only to appease Rarity, but all her conversations seemed to converge towards fruit.

“Gee whiz. Wonder why.”

Rarity graciously ignored her. “These things take time,” she reminded her friend as they walked. “So you’ve ruled out whimsical mares, pragmatic stallions, flower ponies—perhaps we’ve been going about it in the wrong way, do you suppose?”

Applejack seemed to have resigned herself to being ignored. “Who could’a guessed.”

“Perhaps there’s a specific profession that captures your interest,” Rarity mused, thinking of her own tasteful charioteer-themed calendar at home. “Or you might benefit from considering someone closer to you than a near-stranger.”

Living in a small town made that difficult. She ran through a list of mutual acquaintances in her mind; few of them seemed to be suitable candidates, unless Applejack was interested in romance with a side of the dramatique. Somepony with whom Applejack would have a volatile yet passionate relationship—like Strawberry Sunrise, for example.

Rarity slowed her steps, considering. Enemies to lovers surely had to be possible…

“How close’re you thinkin’?” Applejack asked warily. Almost too warily.

The idea struck all at once, and Rarity rounded on her with a gasp. “Applejack, what if the answer to your love has been staring you in the face all this time? What if your true match is one of your closest friends?”

Evidently that wasn’t what Applejack had been thinking, judging from the look on her face, but Rarity was momentous with inspiration now.

She clapped her hooves together decisively. “I don’t suppose this was all a ploy to date yours truly, of course.” A chuckle. “No, it would have to be someone else. Perhaps your feelings are already there, buried under the coarse surface, just waiting for the right push!”

Her friend’s brows were furrowed so low, they were liable to age her face ten years. Honestly, Applejack. “I really think—”

“Don’t think! Feel, with your heart.” Rarity strode down the cobblestone path, dragging the earth pony along with her magic. “Indulge me, at least; would you not go on a date with one of our friends? I’d imagine, even if there were no feelings there, you’d still have a pleasant time. Wouldn’t you?”

It was a victorious dilemma, and so Applejack fell silent. She couldn’t argue with that.

Glancing back at her, Rarity softened her smile. “As I thought. Or, rather… as I felt.”

“With your heart?”

“Exactly!”

“Date AJ?” Rainbow Dash’s nose wrinkled. “Me?”

They’d caught the pegasus outside Twilight’s castle, just after she’d returned a book, and Rarity had posed the question. Over her shoulder, Applejack pantomimed a set of gestures: pointing at Rarity, swirling a hoof at her temple, and rolling her eyes surely enough to hurt.

“I haven’t stopped you from speaking,” Rarity reminded the farm pony.

“I wouldn’t be surprised if you started to,” she snipped back. “Not like speakin’ has been workin’ so far.” She turned to Rainbow Dash. “Don’t know if anyone’s clued you in yet, but Rarity’s on one of her fantasy schemes.”

“It is not a scheme,” Rarity clarified. “It is a venture.”

“I’d venture that you’re spoutin’ nonsense.”

“Well, clearly you wouldn’t know sense if it fell from the sky and bought you dinner. Which several ponies have offered to do, need I remind you.”

Rainbow’s head ping-ponged between them, frown deepening with bafflement. “Uhh, okay,” she said slowly, then looked at Applejack. “She wants me to go out with you?”

Her wings fanned the air, providing her a few extra centimeters of height off the ground. Much like Rarity’s cat, she always seemed to prefer being the tallest in the room.

“Pretty much.” The shadows under Applejack’s eyes were terribly stark under the midday sun. “I obviously tried explainin’ to her that all this romancin’ is a load of hooey, but nothin’ gets through to her. Just tell her you’re not interested, and maybe she’ll finally go harass somepony else.”

“Or agree to one simple date, and open your heart to new possibilities,” Rarity chimed in.

A strange look came over Rainbow’s face, also not unlike Rarity’s cat upon sniffing an unexpectedly alive mouse. “I… huh? But I don’t wanna date AJ. I don’t even like mares!”

That surprised even Applejack. Rarity’s brows shot to the top of her hairline; tentatively, she said, “You… don’t?”

“No!” Rainbow’s tail lashed the air. “I mean…” She grimaced. “I think I don’t? Or maybe I do? Uh…” Her eyes were wide, jumping between the two of them. “Jeez, guys, I don’t know!”

Her wings carried her higher, seemingly on instinct. Rarity looked to Applejack briefly, but no, this was her own area of expertise.

“Well, darling…” She paused, weighing her words. Applejack watched her, undoubtedly knowing she would have the best advice on matters of the heart. Of course. And Rarity therefore delivered with assurance and sagacity: “You might figure it out if you were to go out with Applejack, don’t you think?”

Applejack’s exhalation was somewhere between a scoff and a groan.

Rainbow Dash made a strangled noise. “Argh! I’m not—no!” she exclaimed, then frowned, tipping her head. “Does it seem like I like AJ like that? Does it seem like I—” She cut herself off, scratching the back of her neck, eyes still terribly wide.

“Actually, listen. I gotta go,” she said hastily. “Not because I don’t wanna have this conversation, but… I gotta read to Tank, ‘cause he can’t sleep without it, so. Catch you later, yeah? Yeah. See ya!”

She was gone in a blur of colors before either of them could speak.

Applejack blinked at the air in front of her, then turned to Rarity, whose mouth hadn’t managed to close.

“Congratulations, sugarcube. Y’just gave our friend a crisis. You willin’ to let me go home now?”

“I…”

Rarity was flummoxed. Really and truly, she’d had the best of intentions, although perhaps her methods needed reevaluating. Perhaps if she organized a double date for the both of them, she could solve both of their problems. Two birds with one stone, as it were. A bird pony and an earth pony, at any rate. At least one of them could benefit from a stone to the head.

“One more. One more attempt.” She spoke quickly to cut off her friend’s objecting intake of breath, pleading, “I’m sure of it! Rainbow Dash hasn’t come around, but any of our other friends simply must, and I have complete faith that once you truly connect with somepony romantically, even if it takes sorting through all of Ponyville, you’ll understand what I’m attempting to do here, Applejack!”

Applejack huffed out a breath of air too sharply to be a laugh, flat gaze locking with Rarity’s. “No, you’re the one who doesn’t understand,” she retorted. “I ain’t gonna get on with somepony that way. Not now, and…"

Her voice dropped, but it was no less confident. "I dunno, maybe not ever. I don’t know how to make you see that, but I’m sick an’ tired of jumpin’ through your hoops to make you happy, ‘specially when it hurts our other friends.” She lowered her head, letting her hat slant downward. “I tried to humor you, but I’m tired.”

Rarity’s voice scraped together an affronted sound, and she found herself stomping a hoof. “Humor me? Make me happy? Applejack, I’ve been trying to make you happy! If you only—”

“No, you’re tryin’ to make yourself happy. You’re tryin’ to fit me into all your ideas, but I’m tellin’ you I’m happy the way I am, and you can’t keep actin’ like I’m hackin’ down the wrong tree for that.”

She paused, thinking. “Or, well—Granny gets to act like that. And I get to ignore her.”

Oh. Rarity’s lips were pursed, poised to argue, but the anger drained from her at Applejack’s words. That did make sense, she admitted reluctantly.

“But I… I am trying to make you happy,” she insisted, lowering her voice to something less banshee-esque. More refined. “I suppose it’s only my view of happiness, but I want to show you the experiences I feel you’ve been missing.”

Applejack’s face softened at that. She stepped forward to pat Rarity on the shoulder. “Sugarcube, I’m not missin’ anythin’. Well, I reckon we’d all like to get around with Princess Celestia, but. The point still stands.”

Ah, well, that was fair. Rarity had to make sure, though. “You really, truly don’t want a relationship?”

She couldn’t fathom it. Living a life alone with naught but one’s apple orchard for company, no dashing hero to sweep her off her hooves… No handsome beau or suave seductress to fawn over…

Well, none of those happy endings sounded like Applejack, come to think of it. She probably thought the orchard was the sexiest option. Which begged the question: did Applejack find orchards sexy? No, not something Rarity wanted to think about. It was a question for another time, perhaps. Far, far in the future, and only after several drinks.

“I really don’t,” Applejack confirmed.

Well. That settled it, then. Rarity squared her shoulders, tossing her mane over her shoulder. “Alright, then. We might as well inform Twilight that I’m admitting defeat, as it were, since we’re already here and she seemed quite concerned for your wellbeing yesterday. Don’t you think so?”

Applejack smiled faintly. “No idea why that’d be the case. But yeah, sure.”

They pushed the castle’s great crystal doors open together, and Rarity—couldn’t help one more attempt.

“What about Cheerilee?”

“I swear to Celestia—”

They were merrily bickering by the time they reached Twilight’s study, directed through the labyrinthine corridors by Starlight, who wordlessly pointed them the right way. Had they paid a little closer attention, they would have noticed the pallor in her complexion or the words muttered under her breath.

“Well, regardless of your inclinations, or lack thereof, I am still in need of a companion,” Rarity was saying as they crossed the threshold. “And don’t think I’ve forgotten about Rainbow Dash, if she ever is seen again.”

“Hey, Twi,” Applejack said, nodding to their friend, who was sitting at her desk with another unfortunate stack of mail piled in front of her. “Everything goin’ alright?”

Twilight must have been terribly swamped with mail, because she only dipped her head without a verbal response. At the other end of the desk sat Fluttershy, serenely drinking a cup of tea.

Come to think of it, Rarity didn’t know what the yellow pegasus’s love life was like. She knew of Applejack’s, Twilight’s, and whatever there was to know about Rainbow’s, and she resolved to never inquire about Pinkie’s, but her final friend was an enigma.

“Fluttershy,” she said, heedless of Applejack’s attempt to subtly kick her. “You aren’t uninterested in relationships, are you?”

Fluttershy tilted her head curiously. “Oh? Um, actually, it’s funny that you ask.”

“Funny,” Twilight echoed.

“I was just telling Twilight that I’ve actually begun dating somepony.” The tail end of Fluttershy’s sentence was drowned out by Rarity’s gasp, and she leapt forward, hooves hitting the desk in her haste. Fluttershy, to her credit, didn’t shrink back.

“What? How? Details, darling!” she shrieked.

“Well, I went to a lovely concert with a friend, and… um. It was a bit loud, so—can you please stop looking at me like that?”

Applejack nudged Rarity. She blinked and backed away slightly; she couldn’t allow herself to frighten Fluttershy, of course. Their gentle friend was already taking such a momentous step forward in sharing this with them, so she had to be especially supportive, just like she now resolved to be with Applejack. With all her friends, really—regardless of whether or not she understood them.

Really, it was enough of a friendship lesson to write about, were she so inclined. In that respect, it had been a productive day after all.

“It was a bit loud,” Fluttershy began again, “so I went outside the venue, and I met a lovely pony who’s been on a journey of personal growth just like me, and…” Her gaze slipped away bashfully. “Goodness, I hope this doesn’t upset you.”

“What?” Despite her best efforts, Rarity couldn’t help but lean forward again, swishing her tail with suspense. “Whatever for?”

“Well…” Fluttershy inhaled a breath, visibly steeling her nerves. Then she made eye contact, smiling softly with all the admirable grit she’d accumulated over the years. “You’re right. I’m sure you trust and support me, just like Twilight does.”

“Trust and support,” Twilight echoed faintly.

“Of course, darling,” Rarity assured, as Applejack added, “Sure as sure can be, and you can count on it.”

“Oh, good.” Fluttershy smiled with relief, wings rustling at her sides. “Prince Blueblood will be so glad to hear it.”

Silence.

Under the din of Rarity’s screech, Twilight sighed.

Applejack facehoofed.