The Most Magical Night of My Life

by anonpencil

Some Enchanted Evening

Load Full StoryNext Chapter

Cranky didn’t believe in love at first sight.

He believed in love and in physical attraction, sure, but he’d always felt that matters of the heart were somehow more complicated than a passing glance. Perhaps love was like an old dog, that needed to go around a few times, adjust, and get used to things before nestling down in your heart. Maybe you both had to slowly become more like each other in little ways, before mutual attraction actually turned to love. He didn’t know exactly how love worked, but who did? One thing he was sure of, though, was that it couldn’t happen in the blink of an eye, before words were even exchanged.

This knowledge was all well and good, but it did nothing to explain the fact that he couldn’t take his eyes off of this girl.

He’d seen her in only a flash of movement as he was moving through the crowd of smartly-attired ponies, but it was enough to stop him in his tracks. She was lovely, in the way she stood, the way she smiled, even in the way that she was dressed more simply than all the others. The rest of the royal gala faded slightly around her, and Cranky could not bring himself to look away from the scene. She walked through the ballroom, head held high, shoulders back, a gentle residual smile constantly on her face. Her hair was up and back, bound with a piece of pink satin, and she had the most captivating blue eyes. It wasn’t until a few moments of gawking at her had passed before he realized she was actually another donkey like himself.

Donkey or not, she was, without a doubt, the most wondrous creature he had ever seen.

There are times when you naturally know you have to do something, even if you’re not sure why, and even though Cranky didn’t believe in love at first sight, he did believe in his instincts. And the loudest one of them was screaming at him to go over and talk to her.

Cranky ordered his legs to start moving, but they didn’t. He tried again, loosened his tie a little first, and at last, he made a few shaky steps towards her. He was already wracking his brain, asking himself what in Equestria he could say to such a lady. He wouldn’t know where to begin! Would she even stoop to talk to someone like him?

Before he’d made up his mind about what to say, he was already nearing her. Her back was turned, and she was striding towards the massive ballroom windows, decorated with streamers across the top just for the occasion of the gala. As she reached them, she stopped, and he saw her shoulders rise and fall in a short sigh. It was enough to give him pause, and, unfortunately, it was enough to give someone else a chance to make their move.

Before he realized what was happening, he saw a tall white stallion step up to her side. He was wearing a suit, a monocle, and had a carefully styled blue moustache. He oozed refinement and wealth, and Cranky felt a sinking in his chest as the youthful gent smiled down at the delicate lady. Cranky was quickly certain that he had been outclassed.

“Ah, there you are!” he heard the young stallion say in a thick but lilting accent. “I had wondered where you’d gotten off to my dear. Truly, where has the night been going to, we haven’t even had that dance yet!”

He saw the jenny turn her head and smile politely to the stallion, and the charm in even this simple act was enough to set him back a step.

“Oh…” she said softly, barely loud enough for Cranky to hear. “I don’t feel too much like dancing just now.”

“But my dear, I do insist! We’d make quite the handsome couple on the dance floor, don’t you agree?”

“Why thank you, I… I’m not sure what to say,” she said, and he could see her cheeks flush a dusty pink as she spoke.

There was no other explanation, she must be an angel. Her smile, her voice, even the way she sighed was enough to make him certain of this. It also meant that she was way out of his league. The voice in the back of his head, urging him to speak, quieted some, allowing him enough mental power to give a new command: Walk away. It’s not worth pining over something you’ll never have. It’s not worth all the effort, just to experience another failure. Walk away.

It was a voice he was used to. It was the one he had heard when he’d been given a free ticket to the gala by his friend. It was the one that told him not to travel, because where would he even go? It was the voice that said, if you don’t try too hard, then you can never fail, so why try? When it spoke now, he was all too happy to obey.

Cranky was already turning away to go find a drink to pour his sorrows into, when he felt a delicate yet firm hoof clasp onto his shoulder.

“Why there you are!” he heard an enchanting voice say.

Slowly, Cranky turned, and looked into two of the very bluest eyes he had ever seen. He gawked at her, suddenly made from a dream to real flesh and blood before him. She was touching his shoulder, he told himself. An angel was touching his shoulder.

“U-uh…” he stuttered out. “It… seems I am.”

She smiled broadly at him, and quickly threw her front legs around him in a hug. He was so stunned that he didn’t move at first, simply trying to process the feeling of her weight against his chest, the tickle of a few wisps of stray hair against his cheek. The warmth of her breath, and the soft thread of perfume weaving its way through his senses filled his head in a pleasant and dizzying way. At last, after what seemed like ages, he had the sense to reach up with his own hoof and gently pat her on the back. It was the only thing that seemed like it made sense to do, surreal though it was.

The stallion had a very similar expression to what Cranky was feeling, and the two of them looked at each other in bafflement as the jenny released his neck and stepped back. She smiled up at Cranky once again, and he caught a flash of something in her gaze. A command. Bear with me, it said. He still couldn’t be sure what she meant by that, though.

“I have been looking for you everywhere,” she said with a roll of her eyes. “Where in Equestria have you been?”

“I… have been around,” Cranky said, studying her face to see if what he was saying was right. She didn’t seem upset, so he attempted further words. “Just was getting some punch, saying hi to folks. S-sorry.”

“Oh, that’s alright,” she said, giving him a playful nudge. “As long as you’re here now, that’s what matters.”

The stallion gave a soft cough, and she turned to face the noise with a little ‘oh,’ as if she’d forgotten he was there.

“How rude of me,” she said, a soft self-deprecating laugh in her voice. “This is mister… ah… Fancy Pants, was it?”

The stallion nodded, glancing between Cranky and the lady who had quickly linked her hoof around his foreleg. Confused or not, he certainly wasn’t going to protest that.

“Yes, that was it,” the stallion said, his tone a little frostier than before. “I’m afraid your friend has me at a disadvantage, mister…?”

Cranky shook his head to try to steady his thoughts. The pressure of of her hoof against his upper leg was enough to make his head all jumbled up inside.

“Cranky,” he said at last. “Cranky Doodle Donkey.”

To his relief, neither of them laughed at his name, probably too engrossed in this odd bit of interaction. He extended a hoof to the stallion and the two gentlecolts exchanged a brief shake. They both studied each other as they let go, trying to fathom where they stood in this situation, whatever this situation was. The stallion was the one to speak first.

“And how do you know miss Matilda, if I may ask?”

That was a good question, and luckily, Cranky didn’t get the chance to answer it.

“Oh, Cranky here is my escort for the evening,” Matilda said with a light lean against his shoulder. “We’re dear old friends like that, aren’t we Doodle?”

“Um, yes. Dear old friends,” Cranky parroted.

He’d never been called Doodle before, and under any other circumstances, he could tell he’d probably hate that nickname. However, when she said it, it didn’t sound so bad. Just that once, of course.

“Ah I see,” the stallion said with a nod, glancing between the two like he didn’t quite believe it. “It’s a shame he’s been away from your side for so much of the evening. Most escorts would stick closer to such a pretty lady.”

Cranky felt a brief jolt of anger in his gut. How dare this pony imply that he was a bad date! Well, it’s not like he was really her date, but the implication alone still made his blood boil.

“Well,” he heard his own voice saying, more forcefully and more aristocratically than he’d expected, “I was confident Miss Matilda could take care of herself, and go where she pleased. I wouldn’t want her to feel like she was trapped or forced to be around me.”

The words were more pointed than he'd intended, but he liked the way the sounded. The stallion and donkey eyed each other warily, until at last Matilda cleared her throat.

“I certainly didn’t mind a little wandering,” she said stepping between the two slightly to draw attention. “But perhaps you could show me to the punch table? All this chatting has made me a bit thirsty.”

“Of course,” Cranky said with a polite smile, and a quick final glance at the stallion, “Right this way.”

“I’ll talk to you later Mister Pants. Have a wonderful Gala,” she said sweetly, then joined Cranky at his side.

She tightened her hold on his hoof as he turned both of them back into the crowd, towards where the drinks were being served. Once a sea of ponies had made a moving wall between the pair and the stallion, Cranky felt Matilda sigh, and she lessened her grip on him a little.

“I’m sorry about that,” she murmured softly. “He’s been following me around all night, I didn’t know how to brush him off. He’s so young and relentless, I don’t know what he was thinking coming up to me this many times. Nothing seemed to work.”

“That’s okay by me,” Cranky said. “It was a little jarring, sure, but if you needed help, I was happy to give you some.”

“I’m afraid I did,” she said with another sigh. “But it must have been quite a shock to you.”

“...You could say that,” Cranky said with a crooked little smile.

Matilda stopped and then stepped forward to face him. She put on a simple, genuine smile and studied his face.

“Well, at the very least I should introduce myself properly. Hello,” she said, extending a hoof. “My name is Matilda, and I’m very happy to make your acquaintance.”

“Likewise,” Cranky said, taking her delicate hoof.

He hesitated, wondering whether or not to shake the hoof or lean down and kiss it. The moment was long enough that it made her giggle and she withdrew from his grasp just as he made up his mind to go for the kiss.

“So, uh,” he stuttered out. “What brings you to the Gala?”

She shrugged.

“A friend pressured me to do it, gave me a ticket. I feel like I stick out like a sore thumb though.”

“I know what you mean,” he said with a laugh. “Something similar happened with my own ticket. But if it matters at all, you look just fine to me, and it seems folks here like you plenty.”

This time she was blushing because of him, and the sight was all the sweeter for it. He wasn’t usually so suave, so confident, but somehow he was doing well! He was more than content to just ride this newfound ability as long as it lasted, although the voice in his head warned that it couldn’t be too long now.

“Oh, well,” she said, shaking her head. “This just isn’t a place for donkeys, really. This is a pony event, maybe that’s why I’m attracting so much unwanted attention, I don’t think it’s because of my attire or looks.”

“Agree to disagree on that,” he said with a chuckle. “So is that why you grabbed hold of me? Too much unwanted attention?”

“I believe you’re the only other Donkey here,” she said, again joining him at his side. “It kind of made you an easy target to help me out of that situation. Besides, you were the only one I haven’t seen snickering under your breath at my kerchief, or simply leering.”

“No, of course not,” Cranky said, trying to suppress a swelling of guilt. “That would be rude.”

The two began moving towards the drinks area again, still arm-in-arm.

“I’m glad you understand,” she said with a smile. “So, thanks for being my knight in shining armor and all that.”

“Any time,” he said, and really truly meant it. “It wasn’t anything special of me, you did all the work, but thanks.”

He liked the sound of being her hero in some way, but he also knew he was feeling a touch flushed and nervous at the thought. Perhaps his confidence was finally waning, as he’d feared it would.

“Once we get to the punch table, you’re welcome to go back to the Gala,” she said. “I’m sure you have friends to go see and things to do, I won’t monopolize too much of your time. I’ve already imposed quite enough as it is!”

“No, that’s fine!” Cranky said, perhaps a little too quickly. “I’m happy for the company. My friend didn’t even show, even though he’s the one who convinced me to come. Steven can be a hair flakey sometimes… so...”

“Oh,” she said, then paused a moment before speaking, and he felt a brief change in her gait. “Then perhaps you’d like to be my escort after all? I don’t dance really, but I promise I’ll talk your ear off if you let me!”

She laughed, and it was the sound of rain falling on a still pond at night. Cranky could practically smell the evening dew. Usually he didn’t take too kindly to long conversations with perfect strangers but, maybe this once, he could actually make an exception.

“Miss Matilda,” he said, as regally as he could manage, “I would be honored.”


Cranky wasn’t sure how much time had passed, and he really didn’t care. Once they’d reached the punch table, and they’d both grabbed a cup of cider, it felt like the words fell easily from their lips. Whether it was about the gala, food, social issues, childhood experiences, conversation flowed naturally, and Cranky was happy just to let it go on. He’d even mentioned things from his youth that were usually embarrassing, but when she’d laughed about them, he’d felt good instead of ashamed. He couldn’t be sure how she’d managed to do that to him, and he tried not to let himself think about it too hard.

After what felt like a delicious eternity, Matilda sighed and shook her head.

“My oh my,” she said, laughter in her tone. “I’m afraid we’ve been completely ignoring the gala!”

“Really? I hadn’t noticed,” Cranky said, with a laugh of his own. “I’m certainly not complaining. I didn’t even want to come here tonight.”

“Oh no?” she said, raising an eyebrow. “Who wouldn’t want to come to the gala? Even if I feel like I don’t quite belong, it’s still quite a lofty invitation. I thought it’d be exciting, something new to do, I couldn't pass that up!”

Cranky shrugged.

“I guess. Parties and crowds just aren’t much my thing, and I definitely wouldn’t have come if it wasn’t free.”

“Then why did you come after all?” she said, voice playful.

For the first time in their conversation, Cranky started to feel a little uncomfortable. It was a question he’d asked himself several times before, and each time he did, he heard his friend’s voice echoing in his memory. ‘You’re too uptight,’ Steven had said with a dismissive wave of his claw, ‘you never go anywhere. You talk about all these places you want to see, things you think sound interesting, then just shrug them off and grumble about it! Where’s your spirit, your creativity, your sense of adventure! Really, cranky, you don’t want to turn into an old fuddy-duddy before you’re even middle aged, do you?’

“Well,” he said, looking away from his new companion. “Maybe I was just feeling adventurous is all.”

He could feel Matilda studying him carefully, and he wondered if she could sense the bitter defiance in his words. He was here to prove, even briefly, that he was willing to push his comfort zone even when he had no desire to do so. It was a pretty terrible reason to come to a party, and if he was honest with himself, he’d definitely regretted saying he’d go the moment he’d closed his mouth. He prayed that he could keep up the mask for just a while longer, then he could go home, where things were more… comfortable.

“Then you’re the adventurous sort, are you?” she said quietly, in barely more than a whisper.

Cranky glanced up to see her grinning a charming, but somehow mischievous smile. He sensed something in their dynamic had changed.

“...I’d say I can be, yes,” he said, trying to cover the lie in his voice.

“In that case,” she said, leaning close to him and grabbing his arm again. “How about we step away from the soiree for a bit, explore the castle? When are we going to get another chance to do that, hm? I’ve been a little bored with this party anyway, it’s not as lively as I’d expected, and an expedition sounds fun.”

He could feel his sensibilities throw on their breaks, hard. Explore the castle? Were they even allowed to do that? What if they got caught, or got in trouble? Could they be put in prison or exiled from Equestria for invading a royal abode? The idea was completely insane, far too risky, not worth the trouble at all!

But then he caught a look at her face again, and something inside him softened, then melted away.

“Sure,” he heard himself saying, in willing defeat. “Why not?”

His mind instantly began to tell him exactly why not, but he shrugged it off as best as he could. This lady of his was intoxicating, and maybe he was feeling a touch drunk on her. He certainly felt like he was under the influence of some strong substance. She was a little frightening too, very forward, very pushy, but at that moment he didn’t feel much more than slightly nervous. He could ignore his nature for just a tad longer, couldn’t he?

“Great!” she exclaimed, then gave him a tug towards a large golden double door. “Come on, let’s go this way first, before anyone catches on! I’ve been dying to see if we can find the throne room. Then, after that, you can pick the next door we go through! Sound fair?”

Cranky couldn’t have cared less if he got to choose the next door, but Matilda didn’t give him time to say this. She simply rambled on in a hurried, hushed voice as she pulled him away from the punch and the other guests. For his part, he merely allowed himself to be guided, no word or protest. Just a vacant smile, observing Matilda’s every feature as it lit up her face, her enthusiasm radiating out like a life-giving warmth. He knew, in that moment, that he would gladly follow her anywhere she would go, whether he liked it or not.



Author's Note

Please Note: None of these songs are required listening for this story, and you can ignore them if you want. Just, if you wanted to know where I got my chapter titles, now you do.

Next Chapter