The double doors to Celestia’s personal study opened with a bang. Celestia gave a cozy smile at the sight, knowing it meant that a very flustered and nervous student of hers was about to barrel into the room at any moment.
“Sorry… I… made… you… wait, Princess,” Twilight wheezed, her lungs working double time to compensate for the exertion of getting to Celestia’s chambers as quickly as possible. It also didn’t help that the secluded room was at the top of the East Tower, which just so happened to be on the complete opposite side of the castle.
“That’s quite alright, Twilight.” Celestia raised an eyebrow at the makeup that had been applied in agonizing detail to her student’s face. She looked almost identical to the cover of any given celebrity magazine, which Celestia imagined was where she had gotten the proportions from. She couldn’t help but find that, framed on Twilight’s decidedly un-model-like face, the effect was unsettling rather than beautifying. “Though I do wish you had given me some more forewarning that you were arriving in Canterlot. You had me worried. This lack of formality isn’t very much like you.”
Twilight gave a shaky nod, trying her best to ease her breathing. “I just wanted to minimize time wasted. You know, there are only another fourteen hours and twenty two minutes until midnight.”
Celestia paused, her smile shifting ever so slightly as she began to understand the situation. “That is factually correct, yes. However, I have yet to be informed as to its relevance.”
Twilight took this as a chance to launch into lecture mode, co-opting her mentor’s curtains as a background on which to project a diagram. “Today is an important regional holiday, and according to Shorn Fetlock’s Guide To Impeccable Manners, that means that official authority figures need to be seen partaking in what the holiday has to offer. From costumes on Nightmare Night...”
At this, a cartoonish Luna wearing a Nightmare Moon costume accompanying an equally cartoonish Twilight dressed as Star Swirl the Bearded walked across the screen. “To Hearth’s Warming Eve...” Celestia and Twilight figures dressed in red hats flew across the screen on a sleigh pulled by royal guards. “To the Summer Sun Celebration.” Twilight finished with a trio of princesses waving over a group of subjects. “However, I lack sufficient decorum with regards to the concept of–”
“Hearts and Hooves Day.” Celestia finished for her. “And so you have come to me, hoping I might be able to tutor you on the subject.”
Twilight nodded. All at once, she noticed she was mangling Celestia’s curtains, and she released them with an apologetic blush. “I want to know how to date somepony. I made a few attempts in Ponyville using only my dating guides, but…” Twilight gave a wince, looking as though she had just been force fed a particularly large and prickly sour fruit. “...I soon came to appreciate that this was not something I was going to be able to handle myself. And, uh, since you’ve had at least a thousand more Hearts and Hooves Days to practice, I was kind of hoping… well, yeah.”
Celestia gave a chuckle, once more taking in Twilight’s current state. “I am sorry to disappoint you, Twilight, but I haven’t been very up to date on, well, dating for quite some time now. I imagine I could give you some of the more basic advice, but it is hardly something I could teach you with lectures and diagrams. I think it would be helpful if you thought of it more like the process of making friends, because that’s what it really is. Dating is not something that should be forced, but rather something more natural. Beyond that, I can only tell you that nopony has really expected me to attempt dating, and I doubt that they will extend an expectation to you.”
“Why not?” Twilight shook her head. “I was talking to Rarity, and she said that it was unthinkable for a Princess not to have a special somepony on Hearts and Hooves Day, and when I asked Applejack, she said that if something was important enough to me that I was stressing about it that it would be worth doing, and then Dash said it would be cool if I had a special somepony and…” Twilight lifted a hoof to her chest, closing her eyes and taking in a deep breath. “The point is, my friends say that it’s important and I want to make sure I’m representing Equestria’s best interests.”
“I’m not sure that such behaviour is expected of you, but I will agree with Applejack in her saying that it would be best for you to listen to your feelings on the matter. You must know that romance doesn’t happen mechanically, Twilight. It is a product of your heart.”
Twilight sighed. “It can’t be quantified, I know. But surely it can be understood!” She looked at Celestia pleadingly. “What should I do?”
She was met with a comforting hoof pushing through her mane and a warm, solid wing wrapping around her. A cloth levitated to Twilight’s face and gently wiped at the makeup that had so distorted its natural looks. After a few moments of the treatment, Twilight finally relaxed into the bed sheets, the makeup disappearing into the cloth under Celestia’s careful direction. “I’ve never seen you back down from a challenge, Twilight. As I understand it, ‘the most crucial step to understanding anything is experimenting until sufficient data has been gathered.’” Twilight blushed at Celestia’s quotation.
“I did say that, yes, but… how do you test love? If what I do experience is love, then surely I should go on more dates with the first subject of the experiment… right?” Twilight titled her head. To this, Celestia’s response was to climb back atop her bed, the trailing of her wing along Twilight’s back an invitation to join her that Twilight had learned how to read long ago.
“I believe that would be the conclusion to the experiment, my dear Twilight. If you have found somepony you love, somepony that you have real feelings for, whether or not you love them as much as you possibly could becomes less important. Love is not about quantifying your emotions numerically, Twilight, the same way in which friendship is not about the objective value of your relationships with others.”
“But, well, I–”
Celestia cleared her throat ever so softly, knowing quite well that Twilight would quiet down when she did so. “Let me put it like this: which one of your friends do you like the most? Which one is most important to you?”
Twilight’s eyes widened. “I could never– oh. Oh. So… if romance is a personal matter that doesn’t follow rules of logic, then why do ponies separate the feelings it brings from friendship? Isn’t it essentially the same as a close friendship with some additional physical elements?”
Celestia gave no answer for a moment, only giving a soft shake of her head. Putting a hoof to her chin, she continued. “The two are closely related, certainly, but remember that your dynamic with your lover is much more complex than a friendship. You must be willing to share everything you are, everything you have, and everything you value with your love.” She noticed Twilight’s eyes widening in horror, and gave a chuckle. “Of course, you can pace how much of each you share as slowly or as quickly as you wish, if your love is truly genuine.” Seeing Twilight’s shoulders slump back a little, she felt an irresistible urge to tease pull at the back of her mind.
She lowered her mouth to rest just outside of Twilight’s ear, internally giggling at the gulp Twilight gave as she did so. “Also… If you do get to a level of implicit trust with your special somepony, at some point you may even share your body with him…” Celestia took a moment to gauge Twilight’s reaction, hoping to probe Twilight on her preferences.
Upon seeing nothing change in her student’s expression, she said, “Or her…” At this, Twilight gave a small shiver, pointedly looking at a curtain just behind her. Twilight’s hips wiggled ever so slightly and her tail started flicking from side to side. Bingo... “But of course, getting to such a level takes a lot of time and commitment, something I’m sure you are well aware of.”
“Yeah, I guess that makes sense…” Twilight said, rubbing her chin as she thought. “But wait!” She dropped her hoof, her eyes going wide. “What about my studies? I don’t think I’d be able to keep up my work as a Princess, my work as a librarian, my studies for you, and a steady relationship. It just wouldn’t be fair to whomever I was dating! It wouldn’t be fair to you, either.” She tapped her hoof on the carpet for emphasis. “Although… I guess I could try and make a new schedule… Or maybe I could invent a sleep resistance spell? Oh! I could make Spike the prince of bookkeeping… No, that wouldn’t work…”
“Twilight.” Celestia chuckled. “Your special somepony would understand and help you with your hobbies and duties. If you ever needed help, all you would have to do is ask. Trust me, they would be more than happy to help you with whatever you might need, whether you need them to help with some errands or if you need a shoulder to cry on. In addition, as a Princess you can always defer duties to others here at the palace if you feel that your burdens are too great. I would never dream of allowing the work you do here to inhibit your personal life. I would rather you be happy than productive, Twilight, especially if you’re with somepony. And if things get truly desperate…” Celestia trailed off with a dramatic pause before speaking again. “You can always ask me to help you, strange as it may seem that I might wish to help a friend.” The last line was said with the faintest drip of irony, though the playful jab was dulled and friendly in tone.
Twilight grumbled under Celestia’s open smile, giving the smallest of huffs. As she thought, a small brush, held by Celestia’s magic, lightly dusted her cheeks free of any remaining makeup, seizing the opportunity that her pouting presented. Celestia’s only reaction to Twilight’s exasperation was a small, dainty laugh.
“So… let’s get to the matter at hoof, shall we?” Celestia asked. She glanced at the still open door on the other side of the room, observing her sole guard through the entryway. The door crept shut with a quiet click under Celestia’s magical aid. “You asked me if I could help you arrange a date, and that is precisely what I intend to do. I can have a reservation set for you and a potential date at any nearby restaurant within the hour. If you so wish, I could name a number of parks that stay open late, as well as several nearby theaters that would be more than happy to make room for royalty. Being a princess has its perks, you know. I would also not be opposed to letting you and your date use one of the suites here in the castle for your… use, if both you and your companion should so desire.”
“But who should I go out with? Who should I ask?” Twilight asked, her shoulders slumping ever so slightly. “I don’t really know that many ponies up here in Canterlot. And even if I did, how would I know if any of them even saw anything in me? I’m not all that special…”
Celestia fought urges to coo and laugh at the same time, settling instead on something more supportive. The wing that had formerly been resting on Twilight’s shoulder came to wrap itself around the side of her body.
“Perhaps an attempt to date really is overdue for you, Twilight. Maybe a lover could help you to realize how special you truly are.” Twilight blushed at this, scuffing a hoof against the bedding and folding her ears against her head.
“Well, I mean, I–”
Once more the urge to tease overcame the larger pony. “Am I really so foolish, Twilight, that you feel fit to contradict me so often on this matter?”
Twilight made a move to open her mouth, eyes widening in horror.
“Despite the repeated evidence to the contrary?” Celestia asked before Twilight could speak up.
“No! No! Of course not–”
“You think that your understanding of your own inferiority is so much greater than my own that you feel my opinion is not even worth acknowledging?”
“What? Bu–? Princess! You know I would never–”
“Ah, so you simply feel that your advanced knowledge of the subject proves that there is no room for debate on the matter, contrary to the scientific method.”
“I don’t… well, I–” Twilight groaned, flopping onto the bed. “...I’m not going to win, am I?”
“Not a chance,” Celestia said, patting Twilight on the shoulder. “Now come. The only way we will know for sure if there is a pony out there who thinks you are as special as I do is to search for one.”
Twilight swallowed loudly. “Wait, what? You mean right now? Like, as in, right now, now?”
Celestia chuckled. “That would be the meaning of the word, yes. If memory serves, trying to find a stallion or mare to date was what you came to the castle to do, yes?”
“Of course! B-but I thought we’d make some charts first, maybe run a few calculations on what would be the most likely venue to find a good match, maybe dig up a few books–”
Celestia giggled and gently pushed Twilight off the bed, motioning towards the door with a wing. “Come on, my little scientist. Let’s do some field research.”