Twilight Sparkle wanted to ask Rarity a question. It should have been a simple proposition, really. Rarity and Twilight were in the same place. They were already talking, even. 90% of the effort needed to ask said question had already been taken care of. All that was left to do was open her mouth, manipulate her vocal cords, expel some air from her lungs to cause said vocal cords to vibrate, and wait for the sound to be carried through the medium of the cooperative atmosphere and into Rarity’s ears. Foal’s play, essentially. She had asked Rarity questions before, obviously, and she certainly would ask her more in the future, but this one was a little more personal. And a bit more important than which combination of fabric and thread was in vogue this season in Trottingham, though Rarity would likely argue that prioritization.
Instead, she was making inane small talk over tea. She could hear the words slipping out of her lips, almost unbidden, as they filled the time and the interior of the Carousel Boutique with mundane gossip and goings-on. At least Twilight could be grateful that Rarity was good at mundane gossip and goings-on. How else was she meant to know that Caramel and Sassaflash had made up after their latest argument and were officially together again – the second time this week, she was sure – or that Lyra had apparently gotten on her marefriend’s bad side through some sort of zany antics involving time-traveling squirrels? She kind of wished that she could have been a fly on the wall for that particular debacle.
She screwed her eyes shut. A question. One single question! How hard could it be to ask one little question of one of her best friends? At this rate, it was apparently harder than saving the Crystal Empire. She opened her eyes again, glancing around the Boutique again – for the twenty-eighth time, actually – and straightened her back. She was a Princess of Equestria, darn it, and she was going to act like it!
Her “Hey, Rarity?” slipped out and smoothly interrupted her friend’s gentle stream of conversation, bringing ocean-blue eyes framed by elegant purple curls swinging her way.
“Yes, darling?” Rarity answered.
Twilight swallowed. She wished she had drunk something so that she wasn’t swallowing nothing. “Why hasn’t anypony ever asked me out?”
Rarity blinked. Pondered the question. Blinked again. Panicked internally a little and wondered exactly how to navigate this particular emotional minefield. She supposed she should have seen it coming, really. Twilight was a young mare in her prime, and conspicuous in the fact that no stallion or mare had ever dared approached her during the years she had known her. Of course she would wonder. Of course she would ask somepony. Of course she would ask her. Bravely, and with a complete lack of better options, she strode into the breach. “Well, Twilight, emotions are a fickle thing, are they not? Who’s to say that you haven’t left a string of broken hearts behind you? Simply because none have thus far approached you as a suitor, does not mean that there are not willing ponies out there.”
“Well, yeah, that makes sense,” Twilight said, scuffing a hoof across the floor and suddenly finding the floorboards rather fascinating. “But why hasn’t anypony ever even tried to ask me out? Or tell me they think I’m pretty? Or, anything at all . . . “She trailed off, lost in thought for a few seconds, before shaking her head and returning to the present fully. “You girls have all had ponies interested in you at one point or another.”
Rarity glanced up, uttering a silent prayer to Sun or Moon or any other available cosmic beings to spare her from saying anything tremendously wrong here and now. She even offered a free dress to sweeten the deal; who said she wasn’t Generosity? “Well, darling, you have to realize that there are . . . unique circumstances surrounding you which any potential suitor can’t help but be keenly aware of.” Seeing Twilight’s face begin to morph into her patented “I must question everything” mode, she quickly continued. “When you were a younger mare, you were Celestia’s personal apprentice, a national hero, and the most powerful sorceress who had lived in centuries. That’s an intimidating list of accomplishments for one so young, and I frankly suspect that many stallions – or mares, for that matter – likely felt that you were simply out of their league. And then, of course, you grew wings and the problem only compounded itself.”
Twilight sat back on her haunches, stretching out the feathery appendages and inspecting them closely. They seemed like a part of her now; natural and right. It seemed strange to blame them for her personal problems. She opened her mouth to ask a follow-up question, but she couldn’t quite decide on what to ask. What should I do? Seemed like a strong contender, but seemed a little . . . desperate? Yes, that was the word; it sounded desperate.
But Rarity wasn’t done yet. Having delivered the wisdom that should have been obvious to anyone who thought about the question for 30 seconds, she continued onwards to drop the wisdom that should have been obvious to anyone who knew Twilight on a personal level for as long as she had. “And, of course, everypony knows that you have a type.”
Twilight swiveled her head back around to face Rarity, mental gears grinding to a halt as they strained to process what she had just heard. “Wait, what?”
“Your type, darling,” Rarity explained, waving her hoof dismissively. “The type of pony you tend to fancy. Everypony knows it.”
“I have a type?” Twilight asked.
“Well, obviously,” Rarity tittered. The sound was like the clanking of delicate crystals that probably cost 1,000 bits apiece. “You’ve lived up to it time and time again.”
Twilight racked her brain, searching through her combined memories and life experiences from the earliest foalhood days she could remember up to the present. The fact that much of her foalhood was spent in various libraries and classrooms and not even thinking about fellow colts and fillies as friends, let alone as anything else, made it a bit easier. She came up with nothing. Lacking better options, she asked. “What exactly is my type?”
Rarity blinked. Wasn’t it obvious? Well, she couldn’t just tell Twilight. She knew her emotionally confused friend well enough to know that she would demand evidence to back up any hypothesis. “Well, let’s review the ponies that I know for sure you have been interested in, hmm?”
Twilight’s eyes widened and her hackles raised, sensing danger. “Um, no, we don’t have to go that far, Rarity. Really, I’m sure you’re busy!”
“Oh, pish-posh! This is for a friend, darling.” She grinned, looking a disturbing amount like a certain draconequus. “This will be fun and enlightening for you, I promise.”
Twilight’s tail swished nervously behind her. The treacherous appendage never did learn how to follow orders and tended to betray its owner's feelings, regardless of how she felt about the matter. “Umm . . . okay, I guess.” She swallowed nervously. “I’ve never really spent much time thinking about this sort of thing. It’s kind of hard to talk about it so openly, to be honest.”
“A little honesty’s good for the soul, Twilight. Just ask Applejack.” Rarity took another sip of her cooling tea. “So. If we’re to hold a review of your past crushes, I suppose that we may as well start at the beginning. And that, of course, would be Princess Luna.”
Twilight immediately blushed. “I don’t — I didn’t — I never thought about Luna that way!” she stammered, waving her hooves in denial. “She’s a Princess of Equestria and a much older and more experienced mare than me. It would be totally inappropriate!”
“And yet, I distinctly remember you going well out of your way to spend time with her on her first Nightmare Night in Ponyville. An outside observer might even have called it a date,” Rarity said, cocking an eyebrow. A rather poor example of a date, all things considered, but a date nonetheless. Plus, any romantic interlude involving Twilight was probably doomed to a certain degree of awkwardness.
“That wasn’t a date at all! I was just trying to help her fit in and be more confident. As a friend. Just a friend.”
Rarity shook her head. “Whatever you say, darling. However, I feel compelled to add that the way you were watching Princess Luna’s flank every time she turned around was more than a little obvious. Just about everypony noticed. Especially while she was bobbing for apples.”
Twilight’s blush deepened yet further and she buried her head in her hooves. A pronounced “Uggh!” made its way out, signifying her level of doneness with the subject.
“Very well then, darling. Moving swiftly onwards, we must consider your relationship with Starlight.”
“My relationship with Starlight? What’s that supposed to mean?” Twilight asked, raising her head and frowning.
Rarity coughed delicately. “Ah. Well, you see, there was – and still is, to be frank – a bit of a rumor going around that the only reason you were so lenient with Starlight after her surrender was because you took a fancy to her.” That was actually the more charitable rumor. The darker ones implied that Starlight had come out on top of their struggle and reduced Twilight to a brainwashed thrall. Not that she was going to bring that subject up right now, or possibly ever.
“What? That’s ridiculous! I treated Starlight with kindness because she saw the errors of her ways and wanted to do better, not because she’s attractive!”
“So, you admit to finding her attractive, then?” Rarity asked, the corners of her mouth upturned.
Twilight froze and redness crept back into her cheeks. “Um . . . I mean, Starlight has many qualities that could be considered attractive. By other ponies.” She smacked her hoof authoritatively onto the table. “But that’s not why I treated her like I did. I knew that deep down, she was a good pony who just needed a little bit of help in finding a good path. And she’s proven me right time and time again! She’s become a defender of Equestria just like the rest of us and she makes a fantastic headmare for the School of Friendship.”
“Indeed,” Rarity demurred. “Starlight has proven herself to be an intelligent, powerful, dedicated mare with a deep devotion to the ideals of friendship and an immense affinity for the arcane. Very much like the sort of pony one could imagine making a good match for a certain Princess of Friendship I could name.” She smiled slyly at Twilight. ”And inviting her to live with you and spend lots of one-on-one time with you as her teacher? You should have heard the rumor mill have a conniption over that one, darling. The scandal was positively delicious.”
Twilight facehoofed. “Great. Just great.” She sighed. “Are there any other rumors regarding my love life that I need to know about?”
“Two, actually. One of which is largely confined to our little circle and one of which is rather more commonplace. Which would you prefer to hear first?”
“Just pick one,” Twilight said, huffing in annoyance. She was beginning to regret agreeing to this, but in a warped way she couldn’t help but be curious about what other ponies thought of her.
“As you wish. The more widespread rumor concerns Tempest Shadow. Or Berrypop Fizzletwist. Whichever.” Rarity shrugged. “Frankly, it’s the same issue as Starlight all over again. She committed terrible crimes, spent some time with you, and walked away a free mare. Ponies less wise in the ways of Harmony assume that she bought mercy from you in exchange for certain carnal considerations.”
Twilight gaped like a gasping fish. “What? Ponies think I like Tempest that way? That I would do something like that to anypony? That’s absurd! We all nearly died trying to stop her and the Storm King and we forgave her because she did the right thing in the end. We gave her another chance, just like Luna and Starlight.” Twilight most definitely wasn’t thinking about how her stoic, fierce expression and scarred, muscled body still showed up in her more interesting dreams.
“And yet, ponies talk, Twilight. What can one do about such gossip but ignore it? Those who know you are well aware that you would never do such a thing.” She levitated the teapot over to refill her cup. Twilight’s cup sat forgotten at her elbow. “The last one worth mentioning is, frankly, confined to the six of us, Spike, Starlight, and the Princesses.” She paused to sip from her teacup and set it aside. “Some of us — and I will not be naming names — think that your frequent ventures to the other dimension are more due to your infatuation with Sunset Shimmer than anything else. Care to comment on that one, dear?”
“Oh, yeah, they’re totally right,” Twilight said flatly. “I definitely have made my trips over there to hit on Sunset and not to fight Sirens or raging she-demons. It’s all a cover for my secret romantic rendezvous.”
“Hmm, it would be romantic, you must admit. A secret passion stretching between worlds and all that. It would be like something out of a story. You can’t blame ponies for wondering.” She lowered her voice to a conspiratorial whisper. “And I do happen to recall hearing from Princess Celestia all about how Sunset thought your antics in the Restricted Section of the Canterlot Library were, and I quote, ‘completely adorable.’”
Twilight’s blush, which had largely faded from its last flareup, erupted again. “She did? Did she —” she caught Rarity’s knowing look and smirk and fell silent.
“Well, that’s all well and good, but the goal of this little trot down memory lane wasn’t to embarrass you, dear. It was to try and illustrate a point regarding the commonalities that unite the ponies who have managed to catch your eye. Care to wager a guess?”
“Um . . .” Twilight trailed off in thought. “They’re all mares?”
Rarity nodded. “Accurate, yes, but not quite what I was driving at. Care to try again?”
“Well, I was going to say that they’re all powerful and intelligent unicorns, but I guess that isn’t entirely accurate if you include Tempest.”
“Yes, her unfortunate incident with her horn has left her magic rather potent but unfocused. Rather different than an alicorn, somepony who fought you to a stalemate, and one of Princess Celestia’s former apprentices. Do you want to take another guess?”
Twilight shook her head. “Just tell me.”
“Very well, darling. The biggest thing that all of these mares have in common – besides being mares, obviously – is that they are all what you might call bad girls. That’s your type, Twilight, or so the common wisdom holds it. You are primarily attracted to mares who are powerful, dangerous, and have a dark history to them.”
Twilight opened her mouth. Closed it after a few seconds of saying nothing. The gears in her head spun, looking for a counterargument, and came up with nothing. Rarity’s logic had her well and truly surrounded. Her only recourse would be to deny it and, on reflection, that would be a lie. She had to admit, once again, that it was entirely too easy to forget that a mind like a steel trap lurked behind her friend’s sapphire eyes. More than one rival in business had underestimated and learned too late just how perceptive and insightful she could be. “I — I guess I never thought about it that way.” She laughed humorlessly. “I guess that explains why nopony ever asks me on a date. They all probably assume I won’t even give them the time of day unless they’ve almost destroyed Equestria.” She threw her hooves wide. “I should take out a personal ad. I can see it now: ‘Single princess seeks partner in love. Must be magically adept and have formerly been considered evil. Mares only need apply.’ How’s that sound to you?”
Rarity's face twisted with a level of distaste usually reserved for last season’s fashion. “Twilight, please. Only the hopeless resort to personal ads. It reeks of desperation. A mare of your caliber needn’t resort to such things.”
Twilight rested her head on her folded forelegs. “You could’ve fooled me. I certainly don’t have any suitors beating down the door of my castle.”
“Well, perhaps you need to rethink things. Instead of waiting for a paramour to come to you, perhaps you must go to them? If you approach somepony directly and make it clear that you are interested in courting them, then they should be reassured that you are not too far above them.” She smirked. “With your unique preferences, you have a shortlist of qualified candidates. That should make your life easier, one would think. Simply ask one of the ponies you fancy out.”
Twilight stared at Rarity for several long seconds. “Do you really think that’s a good idea? Ponies probably expect a princess to not date a former villain, you know? It might not be a good look.” The Princesses – the real Princesses, Celestia and Luna – couldn’t even stop at a restaurant without it turning into a circus event. What if one of them took a lover? It would be insanity of the highest caliber. Would that same thing apply to her? She usually didn’t get mobbed by rabid citizens – in fact, she couldn’t even get a cab in Manehattan – but she was still royalty.
Rarity frowned. “To borrow a phrase from Rainbow Dash, ‘buck the haters.’ Your love life is your business and nopony else’s. You didn’t give up your personal autonomy when you put on that crown.”
Twilight snorted with laughter. That kind of uncouth language just seemed wrong coming from the most refined and meticulous pony she knew. Which, to borrow another of Rainbow’s phrases, made it 20% funnier when she used it. “So, you think it’s really that easy?”
“I don’t see why not. All of the ponies we talked about are your friends already, so you have a solid relationship and connection with them. As far as I know, they are all single. We all know that, despite their checkered pasts, they are all good ponies and wonderful in their own rights.” She paused in thought, contemplating for a few seconds. “Though you might want to be careful with Starlight. She and Trixie have been rather close as of late, if you take my meaning.”
“Wait, what?” Twilight exclaimed, blinking hard. “Are you sure?”
“No, darling, I’m not sure. That’s why I told you to be careful with Starlight, not to avoid her altogether.”
“Huh.” Twilight’s wings fluttered slightly. “I guess I’ll . . . ask somepony out. That seems really obvious in retrospect, you know.”
Rarity waved her hoof in a dismissive gesture. “Nonsense! We all need an outside perspective from a good friend now and then. Especially in matters as confusing as love.” And especially when dealing with a mare who needed a written guide to hold a slumber party. Which reminded her exactly of who she was dealing with and how she would go about this. “Oh, and Twilight? No checklists.” She would have to try and save her friend from herself on this one, before her Twilighting could get a full head of steam.
“But —”
“No panel interviews.”
“But —”
“No psychological profiles, either.”
“Rarity!”
“My apologies, darling,” Rarity said with a complete lack of apology. “I’m just trying to point out that love is a fickle thing and not subject to your normal kinds of logic and organization.”
Twilight rolled her eyes. “Fair enough. But, um, who do you think I should I ask first?”
Rarity breathed in and out and braced herself for another long conversation. She was going to need more tea for this one. At least she had the comfort of knowing that Twilight was willing to try to find a date. If any mare in their little friendship circle needed to get laid, it was the alicorn Princess of Anxiety.
Author's Note
Happy 2020! This is part of my goal to publish a story each month during this year. Technically it's coming out on February 1st, but I had it done during January so I'm still counting it 
The last few things I've written have been mostly clop. I don't think that's a bad thing, but I did want to write something else. So, I settled on a little Slice of Life story with Rarity and Twilight. I hope you enjoy it!
If you have any constructive feedback or catch any grammar flaws, I welcome them in comments or by PM. If you enjoy it, I deeply appreciate your likes and comments - in fact, I thrive on them.
I realize that the ending is kind of open ended, and that's intentional. I might come back to this idea with a sequel. Even if I don't, I think that was a natural cut point to leave something up to the reader's imagination.
