Chapter 2
The two mares walked down the hall, one striding and the other slinking. The guards noticed with no small amount of trepidation that Celestia had a strange look in her eye, not unlike the one reserved for the desserts presented to her in the royal eatery.
“Princess! Princess, wait!” Twilight looked around, cringing at the way the pair of them were drawing eyes from all of the guards. It was as if Celestia was parading her around the castle, showing her off for all to see. “I thought that… Princess!”
The solar diarch continued to press onward, her wing beckoning Twilight forward with a gentle flicking motion.
“Princess, please, I–” Twilight realized at once what she was doing wrong. Celestia’s faithful student would make no progress with her when she was making a decision, but her friend Twilight Sparkle might. Finally breaking the respectful distance from Celestia’s front that she had maintained until that point, Twilight rounded on Celestia, an earnest look of exasperation in her eyes.
Celestia stopped, her discriminating glance being traded for the gentle gaze she typically reserved for Twilight in her flustered moods.
“Pri–Celestia, this is making me feel really uncomfortable,” Twilight said, glancing around to make sure that there weren’t any guards within earshot. Lowering her voice just to be sure that nopony was listening in, she continued, “I appreciate the importance of getting me out of my comfort zone, but I’m not going to be able to act naturally or confidently if we take this too fast. Can we please just slow down and think this through a little bit?”
“If that is what you desire, then yes, Twilight.” Celestia’s stomach suddenly grumbled, announcing to the world that she was hungry in a rather less than dignified way. “Say, why don’t we grab a bite to eat at the royal eatery? We can talk about how to select a date from there.”
Using her wing, Celestia gently motioned for Twilight to walk forward. The pair rounded the corner, finding a long hallway flanked by guards leading towards the other side of the castle. “Let me know if you see anyone you like,” Celestia whispered into Twilight’s ear, tenderness edged with mirth swimming in her tone.
“That was part of what I was wondering about, actually. I know that in, oh, a bar, I guess, ponies would usually have something to say about themselves. I’m pretty sure that most ponies wouldn’t want to hear a bunch of science mumbo jumbo from me, so, umm… what could I talk about? And more importantly, how would I get to know anything about them just from looking? Besides, they all look the same!”
Celestia opened her mouth to answer, only for Twilight to quietly shake her head. While Twilight would almost always let Celestia speak ahead of her, sometimes she felt the need to speak over her. Granted, she did this mostly in order to save her friends from Celestia’s wrath, but in making new friends, romantically or otherwise, she felt that establishing her boundaries and desires merited the same reaction. She was the princess of friendship, after all.
“I need to know a little bit about them before I want to try. It’s bad enough that we aren’t going to even chart a plan, and if we’re going to make any progress today, I need to be able to make my choices with a little bit of insight. I don’t want a big romance to spring up out of nowhere overnight, but I do want to make sure that I can at least enjoy dating them enough that the date–or dates–we go on are fun for the two of us. Okay?”
Celestia smiled casually, looking about at the different guards. “Of course, Twilight. This excursion is about how you feel, after all, and if you feel that you can’t date somepony you’ve only just met, I wouldn’t dream of forcing you to.” The pair opened a set of double doors, heading down an especially large staircase as they did so.
“Of course not. Only make friends with them.” Twilight’s thoughts, edged with blunted snark, came rushing from her lips before she could stop them. To her bewilderment and relief, Celestia took the joke like any other pony would, giving a laugh instead of a scornful rebuke. When the two arrived on yet another landing, Twilight let Celestia lead the way through yet another passage lined with guards.
“Where should we start, Twilight? A thoughtful, bookish stallion like yourself? We could tour the library. Perhaps a kind, romantic sort of pony? We could try an art museum. Or maybe–”
“Actually, C-Celestia.” Twilight did her best to skirt around a title she so enjoyed using. “I’d like to try and date a guard. There’s always been…something about them that I’ve found… safe, I guess? Maybe I want somepony to look after me?” Twilight rolled her eyes in exasperation. “Ugh! I don’t even know what I want anymore… Searching through my heart is a bust.” She finished off the thought with a single sigh, turning her eyes away from the Princess.
“Trust me, I promise you that we’ll figure something out,” Celestia said firmly, giving Twilight’s cheek a gentle nuzzle. “But first, let’s find something to eat before we make any big decisions.”
Celestia watched Twilight soldier her way through the hallway, irritation turning the younger Princess’ gaze to a piercing stare. Guards, servants, and palace staff ducked out of the way, cowering under her penetrating, searching scans for the perfect date. She eventually broke off her gaze, vocalizing her frustrations towards her mentor. “I hope they have something good on the menu,” she moaned. “I’m starving…”
“Oh, they can make whatever your heart desires,” Celestia said, looking up as she thought. They pushed through the last set of double doors and reached the royal eatery, finding the rather cozy room lined with red velvet overlooking the Canterlot Gardens. “Hmm… I think I’ll go for a–”
“Can they make me somepony who truly cares about me, somepony who’ll respect and love me for who I am, and not just for my title or what I happen to be wearing?” Twilight snapped.
“...nice tomato salad,” Celestia finished, looking at Twilight in concern. Giving a sigh, Celestia pulled over a plush purple chair and sat down, inviting her ex-pupil to take a seat beside her. She did so a little grumpily, slouching into the seat and folding her hooves. “Twilight, dating like this isn’t about making your ideal partner manifest in front of you. Very few ponies find true love on their first try, or even their tenth. Simply getting out there and finding out what kind of pony attracts you is what will allow you to narrow down your search in the first place. Picking any pony would be a good place to start, even if it does end up being a waste of time.” As she said this, a waiter came to them and set out some water for the pair.
Twilight pinched the bridge of her nose with a hoof, sinking her head down a couple moments later to better massage her temples as she did so. The waiter took this moment to ask them for their orders, which they both gave after a moment’s thought, one with impatient insistence and the other with gentle anticipation. The waiter gave a brief nod, then left Celestia facing a very exasperated Twilight. Twilight finally broke her gaze, shifting from exhausted to pleading. “What do you look for in a special somepony, then, Princess?”
Celestia blinked, the question freezing her in the midst of her drink. “As I mentioned, my, ahem, type has not come along in many years.” Celestia set the drink back down on the table, taking a slow and deliberate gulp. She could already see the response Twilight was holding back in her mind’s eye, but silently prayed that her stalling would allow them to switch topics.
Clearing her throat, she decided to bite the bit and get it over with. “Perhaps I am not an ideal comparison. I remember hearing about Rarity’s dating attempts earlier this year. Perhaps you could tell me a bit more about how you–” Celestia was cut off by Twilight waving her hoof.
“No no no, Celestia; enough about me,” Twilight said with a playful smirk. “You didn’t answer my question; I know what a deflection looks like, especially one from you.” Seeing her friend gulp visibly, she pressed her advantage. “So tell me… what do you look for in a potential special somepony?”
Celestia sighed in relief. At least she didn’t ask about what I look for in stallions…. She gave a quick, soft sigh, then gently opened her mouth.
“I suppose it depends, honestly. It has been many, many years since I’ve dated, after all. You must keep in mind Luna has had more experience with dating, especially since her return from being banished. I’m sure being alone for a thousand years isn’t that good for your social life, and–”
“Celestia.” The voice was firm, but not impatient. Twilight noticed the way Celestia pursed her lips at her tone and the faint wrinkle that appeared under one eye, so she softened her tone. “If you don’t want to tell me, you don’t have to. But the sole reason for me coming here was so that you could teach me how to date somepony, and I was hoping that, based off of your past experience, I could glean some insight into how to handle something as delicate as this.”
Twilight looked away for a moment, her voice lowering ever so slightly. “To be honest, it’s just… I just want somepony to hold me sometimes… And, you know, sometimes I wonder if you do, too. But if you don’t want to confide in me, that’s okay. But… everything I tried with my friends back in Ponyville, well... it just turned out horrible, Princess, and even if tonight goes awfu–awfully, at least I’ll get to spend the rest of it with you. And I was hoping that maybe, just maybe, by the end, we might have something else in common for it, too.”
Celestia swallowed, giving Twilight a small smile for her efforts. “If things don’t go to plan, then… I would love to spend the evening with you, Twilight. I am simply… how can I say this? It’s silly of me, ultimately, but I get so used to being judged all the time that I feel afraid to let things slip, you know? I hate to say this, but it’s true: I’m afraid to open up to Luna, to anypony, for fear that the few bonds I truly have might close up if I fail to deliver or if I may say something that would upset or offend them. In truth, you’re the only pony with whom I can really just let go and be myself, and… I suppose, ultimately, it’s no different from how you felt about failing me. I know in my heart that telling you something uncomfortable would never break the bonds that we share, but I still fear it nonetheless because of how precious they are to me.”
Twilight opened her mouth, then closed it again. For a moment, she simply stared at her former mentor, taking in the vulnerability that was written across her body language in capital letters. Her neck was hunched, her gaze only occasionally met her own, and one hoof was pawing the table skittishly, a final barrier between Twilight’s potential judgement and her own naked heart. “I promise, Prin–Celestia. Whatever you feel about dating, I just want to know what you think about it. I mean, Rarity thinks I should find the richest, handsomest Prince I can and live with him in a fantasy palace. Pinkie Pie thinks we’re all her special someponies and that everyone should just give everyone extra hugs when they feel lonely. I find the first one stupid and the second one impossible, but I don’t think my friends are stupid or impractical because of it.”
Celestia pulled her head back up to face Twilight, her more confident, calmer smile reappearing at last. “If that is the case… I think that if I were to choose somepony, they would need to be somepony precisely like the pony you just described. Somepony who was not so afraid of my position that they could not approach me and tell me when I am wrong, but somepony who was not so strong headed that they could not accept the me they saw hiding in the shadows. They would need to be intelligent enough that I could talk to them about my life–as you know, politics are difficult concepts for most ponies, and for good or bad, they are what makes up my life–and yet active enough that I could spend a day around them without feeling bored or strained.”
“Of course, I would want somepony with problems of their own, because I feel… how might I say this? I feel like it would be taking away from a perfect creature to ask for their love and have nothing to give in return, and I feel that my own flaws would become uncomfortable around a pony who is ideal in every way. Lastly, the pony I would date would have to feel empathy for everyone around them. They would need to love my subjects as I do, for a pony who cannot love my kingdom cannot love me.”
Celestia gave a sigh, spent. She glanced at her surroundings again. The room they were in was empty, though if they listened hard enough, the kitchen staff would be able to hear what she was about to say. There were no waiters around, but the ever-present guards would be within earshot if she was not careful. The room had curtains to absorb sound, but the flat walls meant that speaking too loudly could attract undue attention. She mulled her thoughts over in her brain before quashing her cowardice with a reminder of the catharsis Twilight’s acceptance had brought her thus far.
Lowering her voice, she said, “It’s just… sometimes I wish that I could just let go, if only for a day. The dullness of politics has felled lesser ponies, yet I’ve been doing it for hundreds of years. I can’t help but feel as if I’ve lost part of myself in it all, and I can’t feel like I can be myself around anypony anymore, even my own sister. I have to throw up this facade every time I speak to someone because they view me as this empty… thing. An ideal. Perfect and unapproachable. Even trying to attempt to find somepony to date here in the castle is a huge hassle, because none would dare refuse me. They wouldn’t be considering how I feel, only what would happen to them if they declined. It’s incredibly hard for me to find somepony real to be with, because… I– I, umm… Well, this is rather personal, and I’m not sure if I should tell you this…” Celestia looked away, looking anywhere but Twilight’s gaze.
“Wh–” Twilight cleared her throat. “Why not, Celestia? You know you can trust me,” she said firmly, gently laying a reassuring hoof on Celestia’s jittery one, quelling her nervousness with a soft smile. “Besides, nopony is around but us.”
Celestia’s nerves gave a leap at the electrical contact of Twilight’s fur mixing with her own. Against all odds, a battered smile surfaced on her face. The polished oak and scented candles of the the table faded into the background under the power of the simple yet comforting gesture. It was a release Celestia had rarely felt before. If asked, she would have described it as the sensation of being caught from a very long, very slow fall. Suddenly she relaxed, the strain of possible judgement falling by the wayside. It was abruptly replaced, however, by the strain of dealing with old memories, and the pain and shame they brought. But she knew she could stomach them, so long as Twilight could, too.
“Yes, I– Yes. I suppose that is true enough. Very well. Many years ago, I went out on a limb. I gave my heart and soul to somepony I had been intent upon for many years. This pony was rather close to me, and I loved them dearly… but that was as far as it went. They did not love me, but they loved my wealth and beauty. They were fascinated by my world, but found me cloistered and cold. The relationship I shared with them was mechanical. And once I overcame my infatuation, I discovered this harsh reality. As much as it hurt…” Celestia swallowed, her throat suddenly very dry, and a pressure she rarely felt started to build up behind her eyes. “As much as it hurt me, I broke things off with them. They pleaded for me to stay, but not for me to stay. I knew it was the right thing to do, but crushing their passion, regardless of where it was directed, still felt horrible for weeks after. Months, even.”
Celestia paused for a few moments to wet her unusually dry throat. After nearly finishing her glass of water, she continued. “In my depression, my sister urged me to find something to fill the void, like a hobby or a craft. And so I did. Several, in fact. Brewing, baking, chess. But eventually I would master the hobby or abandon it in frustration and the ache would return anew. The resulting relationships all have similar stories attached. Betrayal. Use. Death. Distancing. Dishonesty. My ideal lover is one who will stay by me and love me for me. I have never found them, but I have found something better.”
Celestia paused, looking right into Twilight’s eyes. She tightened her grasp on Twilight’s hoof before she continued. Her entire mind was screaming at her to stop now. Not to jump over the edge and reveal the entirety of the truth, but against the mighty walls of her own withdrawal came the crushing force of the open heart of a pony she loved. There was a sadness in Twilight’s eyes, but the hoof she had wrapped around Celestia’s own gave it a squeeze, and Twilight, her Twilight, gave her a simple nod and a smile. Celestia opened her mouth, forcing her throat not to catch on her words or stumble.
“When we first met, I realized that you had so much raw potential as a unicorn that I knew I had to take you under my wing. To do otherwise would be dangerous, to you and everyone around you. But as I taught you, you became something more than just my student. Something about the way you smiled at me, no matter what I said, and the way you talked with me like any other adult, even though you always had that awe of me. It made me feel… valued, I suppose. I had given up on that feeling, and there were days before I had you by my side where I just felt like screaming every waking moment.” She blushed, her cheeks tinting red ever so slightly, and let loose a small chuckle. “Nopony else knows this, but you helped save me from losing my mind. You gave meaning to my life again, and for that, I thank you.”
Twilight fought down the urge to blush, instead steeling herself against her better instincts and facing her friend as an equal. “Thank you, Princess. For sharing that with me, I mean. I-I wasn’t expecting quite, uh, that. B-but not in a bad way! I’m really happy to hear I’m a big part of your life, because you’re a big part of mine, and, uh, sometimes it feels like you are that pony you were describing. The perfect one, I mean. The one you were worried you were always taking away from. Sometimes I feel like I’m just wasting your time. And then you go and say that, and it means so much to me, and… What I’m trying to say is… I mean, it sounds like you and I could really use one, so... Celestia, will you go on a date with me?”
The waiter chose that particular moment to bring in their food, and found himself faced with a pair of his country’s rulers staring deeply into each other’s eyes. Sweating bullets, he set his platter down as quickly as possible and hastened off back to the kitchens without so much as a single peep.
Celestia swallowed, taking a deep, shuddering breath. “I would… I would very much like to spend more time with you, Twilight. If that is the way you choose to express this time spent together, I would be quite open to the suggestion, though I have some hesitancy. There are some repercussions to be considered, and I cannot promise anything permanent by any means, but I would like a chance to try. Experimenting, yes?”
“Yes!” Twilight nodded. “Perfect! Let’s go find some stallions!”
Abruptly, Celestia found herself being tugged from a table that had just been served two full meals. She gave a hasty apology to the serving staff on her way to the door, leaving herself no time to wonder what had just happened.
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Alright! New chapter. Commence read
...Was Twilight talking about a double date, and Celestia entirely misunderstood?
Major Oblivious reporting for duty.
4340606
Looks like.
4340712
Prediction: Celestia now has to chose whether to pretend to go along, or admit that she prefers mares and have to awkwardly explain to Twilight what she thought she was accepting.
Oh, Twilight, why do you have to be such an oblivious troll?
Oh wow. This is some grade A chain yanking going on here!
My reactions to the last scene in this chapter:
Fantastic.
I hate you.
Beautiful.
You jerk.
Drama.
I was screaming into my pillow for minutes when I saw this. Then I scrolled down...
Exact quote from me after reading that"Oh, fuck you!" Almost rage quit there... I will stick with this though... never do that again. EVER. My heart broke. I swear if this wasn't Twilestia... Then next thing I know, it actually isn't Twilestia! You would do that, wouldn't you?!
Okay... okay... I'm calm, I'm good. 
Also Twilight gave all indications of her liking mares last chapter. Stallions, is she doing this just to conform to what she thinks Celestia's preference is?
Twilight...You really , REALLY need to work on your wording...
Now Celestia is going to face a dilema , and either way it's going to be awkward.
...that moment when you read the last few lines twice before facepalming...
That's just cruel....
Also, grats on trying to use Who and Whom, don't see that too often. Think you might have messed up with it once or twice though.
I know this is gonna sound stupid, but when I read this
My first thought was "Why does no one ever say this? I swear, there's no way I'd be single if I heard someone actually say this."
Wait...what?
!!!
Oblivious Twilight is best Twilight
4340947
Yes. And this is a Twilestia story.
Twilight could just build her special somepony in her basement, really.
And so we wait
4340782 I learned it from you, okay? I learned it by watching you!
4340947
I believe you re-enacted this video.
4340947 4340951 4341318 4340982 4340803 Plot twist! The biggest troll in this story isn't Celestia.
i.imgur.com/qYMSgZi.jpg
Also, that fucking bait and switch at the end. You magnificent bastards. Although it's hilarious to see Celestia getting trolled for once, even if it is by accident.
I do like how you two are willing to explore Celestia's character like this though. A lot of Twilestia stories out there really do portray Celestia as nearly perfect, and it's just oh-so-amazing how she fell for a mere mortal like Twilight, or some other such nonsense. Frankly, Celestia's a pony just like everyone else, she just lives longer and she's better at handling flaming balls of gas (and presumably other magic as well).
Looking forward to the next chapter
That bait and switch. That fucking bait. And. Switch. It was perfect you son of a bitch
Seriously though.... well played.... well played.... First I was like...
... then I was like... 
.... but then... I was like 
quickmeme.com/img/d3/d30abd9bd591a3ebd7cc5c6ea8b33aa14f81dc9bbe0f0ad468433aee969622f5.jpg
"...and on a more superficial level, a nice lavender coat wouldn't go amiss either."
---
You magnificent bastard.
4341919 I'm glad somebody picked up how blatantly Twilightesque Celestia's ideal partner would be. Celestia certainly hasn't.
4340768 Profile picture about sums up that ending.
I think that ending fooled me as well as everyone else. Way to bait the readers with easily achieved Twilestia, only to kill that hope with fire. A fire that shall be named "Twilight being Twilight."
4341400
Not many people on here are old enough to remember that commercial.
4341325 If Twilight was a stallion, the entire story would have been a very short 'Let's fuck.'
'ok!' 
You know, that chapter makes a lot more sense now that I read it while I am wide awake. The jokes are funnier, the deep stuff is deeper. Twilight and Celestia's obliviousness is more apparent. The entire story is a whole lot better when you are wide awake. Way to go Abyss.
...And Knight of Cerebus.
KBO.
4341707 loved that pic!
OH! Twi... how could you? Here I am getting excited for Twilight finding her true love... and she still screws it up! Well here we go again, five hundred points for the surprise ending leaving me both enraged with a fictional cartoon pony and hungry for more. Kudos to Celestia for not straight smacking Twi in the head and one more Kudos to Pinkie for extra hugs when we're lonely.
s3.amazonaws.com/thumbnails.illustrationsource.com/huge.103.519958.JPG
OMG!
OMG!
OMG!
OMG!
OMG!
OMG!
That pretty much sums up my reaction to this. Excellent chapter from start to (WTF?!
) finish.
Twilight....In the ways of the Mind (including magic, science, etc.), you are a genius, prodigy, and hero with skills surpassed by nearly all. One who is willing to do so much for friends, family, Princess(es), and Country, without ever wanting to seek power or fame. That is why I have you ranked 2nd fav among the Mane 6.....But in the ways of the Heart (including certain emotions, and social skills/ques).....*Sigh*....You're almost (and I'm going to say 'almost') as naive and oblivious as you probably were as a foal/ young filly (which at times drives me to no end....well that, and how you tend to make mountains outta molehills). Which is also why I have you ranked 2nd.
I was all
And then at the end i was like...
Twilight... your such a stupid smart pony...
This was a great chapter and i look forward to reading more!
Yessss
She asked!
after reading chapter two I went straight for the like button, only to find out I've already liked this story, oh the disappointment
Um... Care to explain that again twi? It sounded like you asked celestia on a date, then told her you were both going to look for some saloons. I'm kinda lost what you meant
4341527
Pretty much, just angrier.
4341702
I know, right?!
4340989
Gaaah, Twilight... I figured.
4349133 What she was actually asking was if Celestia would like to go on a double date with some stallions (male horses/ponies) with her.
That last part kind'a depressed me more than amused me. For Celestia to open her heart like that, to take that chance again, just to receive that reaction of misunderstanding... that's gotta' hurt.
someone get me a darth vader gif
doesn't matter which one
just
vader
there will be penance for this, you two
4355541 images5.fanpop.com/image/photos/31100000/cute-puppies-puppies-and-more-31104113-1024-768.jpg feel any better?
You're evil it was supposed to be the starting of twilestia in this chapter!!! I hate you!!!!......... dang it, you've wrote too many great stories for me to hate you. Curse you're talent in writing!
4357775
Broken images make me feel worse!
I'm fairly certain the site you're trying to hotlink that from prevents hotlinking. It might show up on your screen, but it probably won't for everyone.
4363486 Haha, just right-click the link and hit open in new tab. Problem solved!
4357775
4363496
Cute puppies? No, wait!
4359110 they are probably gonna drift closer in the next chapter
Awesome chapter. Keep it up
a
___________________________
I find it funny how Twilight likes mares but denies that fact to herself. Can't wait to see Twilight get some Tia-Lovin', or when it clicks that she likes mares more than stallions.