Dashverse: Date Night

by Chengar Qordath

Rating: teen
Tags: Twilight Sparkle, Cloudkicker, Slice of Life, My Little Pony: Friendship is Magic, Alternate Universe, Rainbow Dash, Romance, Drama, Comedy
Length: 13798

Twilight Sparkle, the neurotic shut-in friend of Rainbow Dash, has a date with Cloud Kicker. For some reason, Rainbow doesn’t seem okay with this.

Twilight Sparkle has a lot of things in life: anxiety, a big brother, great friends, inquietude, loving parents, nerves, a place in Celestia’s School for Gifted Unicorns, staggering levels of magic, and uneasiness. (And an obsessive compulsion to categorize everything, but that’s not important.) What is important is that something new is being added to that list: a date.

Cloud Kicker asked her out, and it’s too late to back out of it. Plus, everypony is so excited for her, though that might just be because they were all worried she would never actually go out on a date. Now she just needs to survive the date itself.

That, and figure out why Rainbow Dash is acting so strange about the whole ordeal.

Published 2015-12-10 09:50:02 UTC
Last updated 2015-12-10 09:50:02 UTC

A Date Where Nothing Goes Wrong At All

I was going on a date. Twilight Sparkle, the former friendless wonder shut-in voted ‘Most Likely to Die Alone’ in her class at Celestia’s School for Gifted Unicorns, had a date. That should have been good news. There was just one slight problem with it.

I groaned and smacked my head against my desk, crumpling up my twentieth attempt at planning out my first date. Despite having gone through several books on the subject, I just couldn’t come up with a good plan. Apparently date planning was another one of those annoying subjects where practical experience counted for more than theoretical knowledge. I hate subjects like that.

Unfortunately, I must have hit my head a bit louder than I’d intended, because a moment later Mom tapped on my bedroom door. “Twilight, is everything okay?”

I sighed and answered honestly. It’s not like Mom would be fooled if I tried to lie to her anyway. “No. I'm doomed.”

Mom opened the door and trotted in, gently rubbing my back the way she always did when I was upset. “Doomed? Don’t you think you’re being just a little dramatic?”

I buried my head in my hooves. “But I have no idea how to go on a date, and nothing in any of my books is helping! How am I supposed to project confidence and desirability or seem interested while also keeping my date at hoof’s length? It all sounds simple enough in theory, but actually doing it...” I rubbed my forehead to try and ward off the growing migraine. “Not to mention picking the restaurant for dinner, and any other activities we might want. Each book uses different criteria for a ‘perfect’ date and I have no idea which one is right!”

Mom started rubbing my shoulders—another one of her old habits from when she needed to comfort me whenever I’d had a bad day, which had happened far too often when I’d been a little filly. “It's really not that hard, sweetie. Trust me. Besides, it’s only your first date. It doesn’t have to be perfect, you’re still just getting to know each other.” She paused, and a very slight frown crossed her face. “And hasn't Cloud Kicker been on dates in the past? Not to mention that since she asked you out, I believe responsibility for planning it all out falls on her.”

“That is the usual social convention according to what I read,” I reluctantly conceded, suspecting Mom was building up to something.

“Then planning the date really isn’t something you need to worry about, dear.” Mom smiled and nodded to herself. “That’s your date’s responsibility. And in any case, a first date really isn’t all that different from hanging out with your friends. After all, you’re still getting a feel for each other. At the end of the day, you still go out and have some fun with another pony.”

“But it’s not just hanging out with one of my friends!” I protested. “It’s a date! The stakes are so much higher now!”

“Don't overthink it.” Mom pulled out an old, well-used brush and got to work fixing up my mane. “Trust me, Cloud wants to have some fun, just like you.”

Have some fun. That was one way of putting it. I liked to think I knew Cloud reasonably well after that mess with Trixie and the talk we had in Cloudsdale, but there was still a lot about the mare that was a complete mystery to me. Most significantly, her overactive sex drive.

I still wasn’t sure why she’d asked me out at all. She’d never expressed any interest in—well, she might have expressed her interest in doing a few things with me that I certainly wanted no part in, though I suspected those offers weren’t unique to me. Cloud Kicker was a notorious tail chaser, after all.

And yet, she’d asked me out on a date. And for some reason I still wasn’t quite sure of, I’d gone and said yes. Even though I had no interest in ... that, I still wanted the date to go well. After all, it was my first date ever. It ought to be a little bit special.

There was just one problem with that plan. I still had no idea how to make a date feel special. “But ... but what if I say something that makes her not like me?”

Mom chuckled as she slowly ran the brush through my mane. “I can't see you doing that. If anything, she'll probably be flattered that you're so nervous around her. After all, you wouldn’t be such a nervous wreck unless you really liked her and wanted the evening to go well.” She paused a moment to work out a small knot in my hair. “Really, dear, you don't need to treat this like a test where one wrong answer ruins your perfect score.” She tsked and got back to work on brushing out my mane. “Like the time you came home in a panic because you’d only gotten a ninety-five on a test.”

“Don’t remind me...” With a couple years of hindsight, I was a little embarrassed that I’d spent an entire day locked up in my bedroom, certain I was going to get kicked out of the School for Gifted Unicorns. At the time, it had seemed like a perfectly rational response. I rubbed my face. “I just ... I really don't want to mess this up. I mean, who knows if anypony will ever ask me out again?”

Mom smiled and nuzzled me reassuringly. “Now now, there’s no call for that. I'm sure there are plenty of ponies who would love to ask you out. You just need to keep an open mind and not be afraid of putting yourself out there.”

My ears wilted, and I grumbled sarcastically under my breath. “Yeah, sure, everypony’s lining up at the door to ask me out. That’s why the only time I ever went to a school dance was when Shining Armor pretended to be my date.”

Mom put a hoof under my chin, gently tipping it up so she could look me in the eyes. “Twilight, what’s bothering you?”

I thought about telling Mom the truth. That a couple months ago, during the competition in Cloudsdale, Cloud Kicker had let slip that she liked Rainbow Dash. But now Cloud was dating me. Why? Was this just some sort of trick to get Rainbow Dash’s attention?

I’d read a few books where ponies did things like that. And I couldn’t imagine any other reason a pony like Cloud Kicker would want to date a pony like me; I wasn’t attractive, and even if she did somehow talk me into sex, I couldn’t imagine I would be any good at it. That one time I’d tried to read a book about it, I’d nearly blushed to death before I was five pages in. I certainly couldn’t hope to compete with Rainbow Dash. Brave, athletic, charismatic, and supremely confident, not to mention Princess Celestia’s personal student. Nopony could beat that.

But I couldn’t tell Mom about all of that. “I just ... I don't know. I'm worried about the date, I guess.”

Mom smiled reassuringly, patting me on the cheek. “Don’t worry, that’s perfectly normal. I'm sure you'll do just fine.” She paused a moment, then went back to fixing up my mane. “It really is good to see you finally going on a date.”

I blinked in surprise. “It is?”

Mom gave me a reassuring pat on the back. “Of course, I want you to find somepony you can be happy with. To be honest, I was starting to worry that—” She cut herself off, and there was an awkward pause before she said, “Well, never mind what I was worrying about. I’m a mother, I’m supposed to worry too much about silly things.”

She might not have finished the sentence, but I could guess what she would’ve said. She’d been worried that I would never find somepony who wanted to date me, and I’d end up dying alone with only my books to keep me company. Which was still how things were likely to end, since I couldn’t imagine this date going the way Mom hoped. Nopony wanted to be with somepony who was dangerous if she ever lost control.

Her next remark made me all the more certain of that. “If this Cloud Kicker does turn out to be the one, then so much the better.”

Oh Celestia, Mom was probably already dreaming about me getting married and providing her with grandfoals. I suppose I should’ve expected that, considering Shining’s wedding had everypony thinking about marriage. I needed to do something to nip this in the bud before Mom got her hopes up. “Er, Mom? What if she's not the one? She probably wants somepony else. Somepony better than me.”

Mom immediately hugged me, making me jump in surprise. “Nonono, you can't think like that. You are a wonderful young mare, and you deserve this. You're smart, and pretty, and would make a fine fillyfriend for anypony.”

Even though I knew she was just saying that because she was my mother, and thus incredibly biased, a part of me wanted to believe that was true. “Really?”

Mom smiled and nodded confidently. “Positive.”

Despite myself, I could feel a hesitant smile tugging my lips upward.

Mom grinned and squeezed my shoulders. “See? You’ll be fine. Now all we have to do is make sure Cloud sees you for the beauty you are.” Her horn lit up, and a small suitcase hovered into the room. “Now, your friend Rarity was kind enough to loan me a few things to help you get ready for your big night. I suspect she wanted to help with all the pre-date preparations too, but I had to draw the line there. I’m your mother, I wanted to do this myself.” She started humming to herself as she opening up the case, revealing a ridiculously massive collection of cosmetics. Mom’s smile slipped just a bit as she took it all in. “Oh ... that is quite a lot of it.”

I glanced nervously at the collection of makeup that could probably outfit a small army. “You do know how to use it all, right?”

“Of course, dear,” Mom assured me, pulling out a few things and studying them. “Just because I’m a married mare doesn’t mean I’m completely out of touch with the dating world.” She held up one case, turning it over in her telekinetic grip. “Now if I could just figure out what this ... oh! False eyelashes. We don’t need to worry about those.” She poked through the massive makeup case for a bit longer, slowly pulling out a collection of bottles and strange devices that seemed to be what she was looking for.

Then she got to work slathering all of it onto my face. Well okay, she was actually applying it all very delicately and with an expert touch, but that didn’t change the fact that it bothered me. Despite my best efforts to sit still and endure it, I started twitching and shifting. Mom frowned, then used a tissue to wipe away an errant line of lipstick on my cheek. “Twilight? Is there anything you want to talk to me about?”

I sighed. “Makeup feels weird.” The closest thing I could think to compare it to was when my face had been covered with mud during one of my misadventures with Rainbow Dash. Except this time I couldn’t wipe all the gunk off my face, I just had to leave it on.

Mom chuckled and smiled. “Don’t worry, you’ll get used to it.”

I couldn’t imagine ever getting used to having a layer of weird powders and liquids over my face, but I didn’t want to argue with her. “I guess...”

She seemed satisfied with my answer, and finished covering me in makeup quickly and efficiently. “Now then, on to the dress—which Rarity also provided. Do remember to thank her for all her help next time you see her.”

“Yes, Mom,” I answered dutifully. Though a part of me wasn’t sure what to think of how much Rarity was helping out. She was probably just being generous, but I couldn’t help thinking that all these gifts came with certain expectations about how my date would go. If I wound up making a disaster of it all, Rarity would probably be very upset with me for wasting all her hard work. “Can I see it?”

“Of course.” Mom pulled out a dress that ... well, I could tell it was one of Rarity’s designs. She always likes to make her dresses grand and elaborate, with as much flourish as possible. To be honest, I’d never really been comfortable wearing any of the clothes she made. They were just too much. Dresses like that belonged on fashion models or noble courtiers, not ... me. Every time I wore one, I just felt like the dress was swallowing me up and overshadowing me so much that nopony actually noticed me.

I tried to find some way to put all of that into words without insulting my friend’s work, and failed miserably. “Isn't that bit ... much?”

Mom chuckled and waved my concerns away. “For a romantic date, of course not. I mean the thing I wore on my first date with your father...” She trailed off, then pointedly cleared her throat. “Yes, it should be fine.”

I didn’t want to disagree with her. “If you say so...”

Mom picked up the dress and carried it over to me. “Relax dear, your friend is one of the most fashionable ponies I’ve ever met. If she thinks this is the best dress for you to wear on a date, you would do well to listen to her advice.” She got to work on helping me into the dress. “You'll do fine, trust me. Show a little bit of confidence and it will work out.”

I took a deep breath, then tried to put a confident, happy smile on my face. Faking a good smile was one of the few social skills I’d ever mastered. It was the only way to keep Mom and Dad from worrying about me all the time.

It worked. Mom finished helping me into the dress, then smiled back. “There, much better. And really, don’t worry too much about it being a date. Just try to enjoy yourself. If there’s any romantic future for you two, it’ll happen naturally—and if there’s not then you can still have a pleasant evening. Either way, you’ll come out ahead.”

I kept my fake smile carefully in place, but didn’t say anything. Mostly because all I could think was that I was probably going to let her down.

“Twilight,” my brother chided, “you’re going to wear a groove into the floor if you keep pacing around like that.”

I groaned and halted, whirling on Shining. “But where is she? Our date’s supposed to start in fifteen minutes!”

“Which means she’ll be here in fifteen minutes.” His voice was almost infuriatingly calm. Didn’t he understand that I was going on a date, and this was a big deal?! I swear, my big brother can be such a doofus sometimes.

“Why are you even here?” I grumbled. “Shouldn’t you be spending time with your wife?”

Shining shrugged. “We had to delay the honeymoon a little on account of evil love-sucking bugs trying to take over Equestria in the middle of our wedding. And Cadance wanted to be here, but she got held up at the palace: too much work, and not enough ponies to do it.” He paused and smiled. “For what it’s worth, she said good luck, and that you two would make a cute couple.”

I nearly jumped out of my dress when another voice called out through the window. “Oh, please. Cadance thinks everypony would make a cute couple.”

I turned to the window just in time to see Rainbow Dash fly in. “Rainbow? What are you doing here?”

Rainbow waved to my brother, “Hey, Shiney-hiney.” Then she shifted her attention back to me, pausing as she looked over my hair, makeup, and fancy new dress. “Hey, Twilight. You're ... wow, look at you. Who knew a dress and some makeup would turn you from a slightly cute nerdy unicorn to a pretty-hot-and-nerdy-in-a-cute-way unicorn?”

Despite her utter lack of diplomacy, I still felt my cheeks warming up. “R-really?”

“Really.” She paused, and her smile slowly transformed into a frown. “Actually, maybe you look a little too good. We need to tone that down, or it'll give Cloud ideas.”

“What kind of ideas?” Shining rumbled, his big brother instincts coming to the fore.

I rolled my eyes at both of them. “You two are being ridiculous. She already flirted with me all the time while I was just going around looking like my normal self, so I don't think me wearing a dress is going to change how she sees me.”

“That’s ‘cause Cloud’ll flirt with anything that has a pulse,” Rainbow grumbled under her breath. She shook her head, ane returned her attention to me. “But that’s not the point. If she sees you looking like this, she might try to do more than just flirt.” She frowned, tapping her chin thoughtfully and staring at me. “All right then, let's work on your mane, or maybe take some of that makeup off. Just, y’know, tone it down a little so Cloud won’t get all weird on you.”

“Rainbow...” I cautiously put a little distance between the two of us. Once Rainbow had an idea she tended to act on it, no matter how terrible or short-sighted it was. “I worked very hard with my mom to look like this, and I'm not going to just change it because... What? She will act more like herself? If that's possible?”

Rainbow let out an annoyed snort. “Hey, I'm just keeping an eye out for you. I mean, you've never gone on a date or anything before, and Cloud's been on loads of them. She’ll probably try to bang you or something if you go out looking this nice.”

I scowled at her, starting to feel more than a little annoyed myself. “I think I can handle that. You’re acting like she’s never flirted with me before. I've been able to turn her down for ... certain activities in the past, and I don't see why that would change tonight.” I tilted my head to the side, trying to make sense of her strange behavior. “Is that what you're so concerned about? That Cloud will try and seduce me?”

Rainbow’s ears wilted, and her eyes flicked around the room guiltily. “I'm just trying to protect you, is all. I mean, I know you’ve never done any of this romance stuff, and Cloud’s kind of a pro at it. So, you know...”

I sighed patiently, reminding myself that Rainbow meant well. “What are you trying to protect me from? Being romanced by one of your old friends? Look, I'm happy you care, but I'm a big filly. I can make my own choices. And really, it's not likely anything is going to come of this anyways.” My ears wilted just a little as I remembered that Cloud would rather be dating Rainbow than me, and this was probably all just a ploy to try to make Rainbow jealous. “I mean, it’s just one date. Nothing serious.”

Rainbow took a deep breath and slowly nodded to herself. “Just be careful, okay? Don't let her talk you into doing any weird stuff you don’t wanna do.”

I frowned at her. “She’s your friend, Rainbow. If you really thought she was the type of pony who would take advantage of me, I don’t think you’d still be friends with her.” When she reluctantly conceded the point, I continued. “Okay, so realistically speaking, what's the worst case scenario here, in your mind?”

“Um...” Rainbow’s cheeks lit up. “You know, if you and her ... if she got you to ... do ... stuff.”

I broke out the most deadly weapon in my arsenal: sarcasm. “Yes, because me not dying a virgin would be an end of the world scenario, for sure.”

My brother groaned, while Rainbow’s jaw practically hit the floor. To be honest, I was a little stunned I’d said that too. But ... well, it’s not like there’s anything that weird about maybe wanting to eventually have sex someday with somepony. That was a perfectly normal thing that most ponies did at some point in their lives. Yup, I was normal.

Rainbow was the first one to regain her composure, though her voice came out a lot softer and meeker than her usual brashly confident tone. “Just be careful, okay?”

I ran a hoof over my face, nodding along just to placate her. “Yes, yes, I'll be careful. And I assure you, I'm not planning on ending up in a bed with her after only a single date. Or in any other awkward scenarios either, for that matter.” I sighed, my shoulders slumping. “Like I said, I doubt this will even get past the first date. She'll probably get bored with me, or I'll mess something up, or she’ll find somepony else she likes a lot more than me, and that will be the end of it. Leaving my precious innocence safe forever.”

Rainbow frowned at me, taking a hesitant step forward. “You okay, Twi?”

I sighed and faked another smile. “Yes, I’m fine. Really. I'm just a bit nervous, I guess. I've never been on a date before.”

“Hey.” Rainbow put a reassuring hoof on my shoulder and gave me a little squeeze. “You'll be fine. You’re awesome, and Cloud’s real lucky you agreed to go out with her for even one date. I just want you to be happy, is all.”

My smile became a bit more genuine, only to fade away as another thought struck me. “And it's really feeling like you don't think I could ever be happy with Cloud.”

Rainbow’s ears wilted, and her eyes started darting around again. She opened her mouth to say something, then cut herself off, grumbling under her breath and shaking her head. The only words I could make out were “Stupid Cloud Kicker.”

Now it was my turn to comfort her. “Rainbow, is everything okay? Is me dating Cloud upsetting you this much?” A rather depressing thought struck me: if Cloud was really only dating me to make Rainbow jealous, maybe her plan was working. Rainbow certainly seemed upset, and while she could just be doing all this worrying for my sake...

Rainbow snorted loudly. “I'm not upset. Why would I be upset? I don't care who Cloud dates.”

I tilted my head to the side. “Then why are you here?”

Rainbow snorted, her wings flicking in agitation. “No reason. I was just checking up on you because ... reasons!”

Shining cleared his throat. “Rainbow, are you feeling okay? You're acting a bit weird.”

“I'm fine,” she snapped, then took a deep breath and forced a smile and a bit of false cheer into her voice. “More than just fine. I’m awesome. And cool. Yup, totally awesome and cool. Never been better. How're you?”

I decided to ignore the fact that Rainbow was clearly faking her good mood, mostly because this whole conversation had been weird and awkward and I just wanted it to be over so things could go back to normal. “Nervous, but all right.”

“Cool.” Rainbow nodded to herself. “So ... uh ... later, then?”

“Sure.” I sighed softly. “Rarity is insisting I meet her for breakfast so she can get all the ‘juicy details,’ and Pinkie said she wanted to hear how it went too. I suppose we might as well have everypony meet up: I’m sure Fluttershy and Applejack will want to gossip about my date too, even if they don’t come out and say it.”

Rainbow chuckled and shook her head. “Yeah, that sounds like them all right. Just make sure the juicy details aren’t too ... er ... juicy.”

I stared at her for a long moment, then decided I was probably better off ignoring that remark too. “All right then, see you tomorrow. Cloud should be here soon, so...”

Rainbow blinked, then nodded. “Right, gotcha. It’d be kinda weird if I was here when she showed up.” Without another word, she spread her wings and shot out the window.

I sighed and closed it after her, locking it after a moment’s hesitation. I didn’t know what to make of Rainbow’s behavior, but one thing was certain: if Cloud was only dating me to get a reaction out of Rainbow, she’d succeeded.

Cloud Kicker showed up for our date one minute early. I’d parked myself in front of the door so Shining wouldn’t be annoyed by my pacing, which meant that as soon as I heard her hoof on the front door I pulled it open, putting on my very best smile for her. “Hey, Cloud. Good to see you.”

She’d obviously gone to some trouble to make herself look good for the date, though it probably came a lot easier for her than it did for me. Her mane and coat were nicely brushed out, and her wings looked freshly preened, and all of that had probably only taken her five minutes. She was just lucky to be naturally beautiful, while it had taken Mom an hour of work just to get me up to passable.

Then there was her dress. It was a simple single-piece red dress that was nowhere near as fancy as the one Rarity had made for me, but of course Cloud looked far better in something she probably bought off a rack than I looked in a designer outfit. Especially since that slim red dress clung to her body in a way that drew my eyes to places that they really had no business going. That was the thing that always made Cloud so ... I don’t even know if there was a word for it. But whenever she was around, I just seemed to notice things about her and other ponies. Things that I normally was very good at ignoring.

Cloud smiled, her eyes openly going up and down my body. She wasn’t leering at me or anything like that, just ... looking, and not trying to hide it. “Hey, Twilight. You look amazing.”

Despite expecting the obligatory compliment, I still blushed. “My mom helped a lot. And Rarity, for that matter. Though I feel a bit silly. Like the time when I was a little filly and tried to dress up in Mom’s clothes and wear her makeup to prove I was all grown up.”

She grinned and lightly shook her head. “Well you look really good, and there's nothing silly about that. Trust me, there’s no way anypony’s gonna mistake you for a kid playing dress-up. Ergo, you shouldn’t feel silly.”

The shy smile on my lips wasn’t nearly as big as the one I’d greeted her with, but it felt a lot more genuine. All the compliments also made me feel just a little bolder than normal. “Well, you aren't looking too bad yourself. I like your dress.”

“Thanks, but it’s got nothing on yours.” She chuckled and waved at my fancy ensemble. “I’m sure Rarity would be horrified to learn that one of her custom designs is being worn alongside a dress I bought from Bargain Barn for twenty bits.”

“I’ll leave that detail out when she asks me for gossip,” I assured her.

“Or you could just ... massage the truth a little,” she suggested with a playful grin. “Say my dress was from La Grange Marchander.”

I gave her a flat look. “I’m pretty sure Rarity would know that’s just a fancy way of saying Bargain Barn.” Not to mention her translation had been rather iffy.

“Still worth a shot.” She shrugged. “Anyway, we’re not going on this date so Rarity can criticize my fashion sense. Speaking of date plans, have you ever been to Cloud Nine?”

Since I’d never been on a date before, I hadn’t really been to any fancy restaurants. When I did eat out, it was usually just something like a mid-study snack at Doughnut Joe’s. I’d heard of Cloud Nine, but didn’t really know anything about it beyond the fact that it was supposed to be really nice. “Can't say I have, no.”

“Good, because I got us reservations there.” Cloud grinned and stepped out of the doorway, and I hesitantly stepped out to follow her. “You'll love it. It's an amazing restaurant. Rainbow, Vinyl, and I went there for my big pre-graduation party.”

My next step faltered as I nearly tripped over my own hooves. The last thing I wanted to hear or think about right now was Rainbow Dash. And the fact that Cloud was taking me to a restaurant she’d gone to with Rainbow was ... well, it was making me think about Rainbow.

We were about to head out the door when Shining trotted over. “One moment, there’s something I want to settle before you two head out.”

I glanced back at him, utterly mystified by what he might be up to. “Huh, what is it?”

Shiny ignored me, fixing his eyes on Cloud Kicker. “What time will you have her back?”

“Shiny!” I protested, struggling against the urge to either blush to death or smack him with the nearest blunt object. “I'm not a little filly!”

My big brother continued ignoring me like the big, overprotective doofus that he was. “I want her back no later than ten. And if you break her heart, I'll be breaking something of yours.”

I rolled my eyes and tried to shut the door in his face, but he put his hoof in the doorway to block me. “She's not going to be breaking my heart. This is our first date.” I groaned and rubbed my forehead. “You’re being completely ridiculous and embarrassing me.”

Cloud grinned and snapped a mocking salute off at my brother. “Relax, Captain. I'll be a perfect gentlemare and treat your sister like the classy lady she is.”

Shining’s gaze shifted back and forth between the two of us, and he reluctantly nodded. “All right, I guess that’ll have to be good enough.”

I glared at him, though there wasn’t any real anger behind it. “Are you done playing protective big brother?”

“For now. And who said I was playing?” He stepped out and gave me a quick hug, then very slowly let go of me. “Have fun, Twily.”

I smiled back at him as I slowly turned around to join my date. “I'll try.”

Cloud grinned as well, her relaxed smile showing off her limitless confidence. “Don’t worry, I’ll make sure she doesn’t just try to have fun.”

Her certainty should’ve reassured me, but instead it just made me feel worse. I usually associated that limitless self-confidence with Rainbow Dash. Maybe it was something Cloud had picked up from her, since they’d known each other for so long? In either case, it was just another reminder that Rainbow should be the one dating her instead of me.

Cloud Kicker led me down the street for a few minutes, and we chatted about Star Swirl’s Third Law of Transfiguration. Well, I told her about it. I’d just read a book on the subject, I was allowed to be a little excited. She didn’t seem to mind listening to me, so it was all fine.

I was so wrapped up in the discussion that it took me a moment to realize that we’d stopped walking. Cloud looked up, and when I followed her gaze I realized we were standing beneath a large patch of clouds. “You're gonna have to hop on for the next part. We're going airborne.”

I gave her a flat, suspicious glare. “You planned this from the start just so I’d have to mount you, didn't you?”

Cloud chuckled and smiled disarmingly, looking far more innocent than I knew she was. “Would you believe me if I said no?”

Despite myself, I chuckled. “Probably not.”

Cloud grinned and knelt down, spreading her wings. “Well hop on then. And try to keep your wild lust for my hot body in check, I will need to actually concentrate on flying for a bit.”

I rolled my eyes as I carefully climbed onto her back, making sure I didn’t do anything to mess up Rarity’s very nice dress. “Oh yes, you’re so sexy I can barely restrain myself from ripping your clothes off halfway to the restaurant, even though that would send us both plummeting to our doom.” I teasingly poked her in the side. “Just remember how you told my big brother that you were going to treat me like a lady.”

Cloud chuckled and shifted underneath me, helping me get settled in. “Relax, I’m not trying any funny business.” She flapped her wings, and then we were in the air.

I’d never really ridden on a pegasus’ back before. Sure, Rainbow Dash had rescued me from falling to my death, but that was different. For one, I hadn’t been draped over her back. And it hadn’t been in the middle of a date. So I hadn’t noticed things like how her powerful wing muscles shifted and moved with every single flap. Or how warm and nice her coat felt. Or how nice she smelled.

Oh Celestia, now that Cloud Kicker had gotten me thinking about her that way, it was impossible not to. Even though I knew I really shouldn’t be. That sneaky, sneaky mare. She’d used a joke to put the idea in my head, and now I couldn’t get it out.

Thankfully, we weren’t in the air for too long. As soon as she reached cloud level, I discovered that the random patch of clouds over Canterlot was actually nothing of the sort. There were tables set up all over the clouds, and nicely dressed pegasus waiters bustling back and forth between them. Cloud looked back at me and grinned. “And that's Cloud Nine, my favorite restaurant in Canterlot.” She swooped down and landed gently. “The clouds are all enchanted, so you don’t need to stay on my back unless you want to.”

My cheeks lit up again as I gingerly climbed off of her. To keep my mind off the fact that I’d been far too close to her, I focused on the magic at work on the clouds beneath me. “Huh, interesting. It looks like a modified version of the cloudwalking spell, except the spell matrix has been inverted. And getting the magic to stick to clouds must have taken a lot of work to—”

“It is pretty impressive,” Cloud very gently cut me off. “Though you probably shouldn’t poke at the spell too much. You wouldn’t want to accidentally disrupt it.”

For once, my blush had nothing to do with Cloud Kicker. “Oh. Right.”

Cloud chuckled. “Always curious. But yeah, that is kind of Cloud Nine’s big selling point: for all the non-pegasi who don’t happen to be friends with a highly talented magical prodigy, this is the one of only ways they’ll ever get to walk on clouds and see what it’s like to be a pegasus.” She waved a hoof down at the city below, which glistened in the light of the setting sun. “And it's hard to argue with the view.”

“It is pretty impressive.” I turned to her and smiled. “Okay, this place is pretty nice, even if you did just pick it so I’d have to ride on your back.”

She grinned. “Told you. And I didn’t hear much more than a token protest about needing to mount up either. Maybe you liked it?”

I felt my cheeks heating up again and quickly changed the subject. “So what type of food do they serve here? Is it pegasi cuisine, or...?”

“No, they go for the classic high class cuisine.” Cloud grinned. “After all, this is still a Canterlot restaurant, even if it’s set up in the clouds.” She glanced over, catching the maitre d's eye. “Just gimme a second to get our table set up. I’ll be right back.” She trotted off to go talk to him.

With nothing else to do while I waited for her, I took a moment to admire the view. With the sun setting all the lights in Canterlot were starting to come on, giving the city an almost ethereal quality and adding a rich panorama of colors to the simple white marble that usually dominated the city’s colorscape.

However, then something spoiled my view. A single rogue cloud drifting through the sky, a tiny bit of rainbow-colored tail poking out the side. I tilted my head to the side, then glanced back to check on Cloud Kicker. She was already done talking to the head waiter, so as soon as she returned I pointed to the cloud. “Am I seeing things, or is that...?”

The cloud let out a muffled curse and hastily pulled its tail back inside before Cloud Kicker could spot it. Her gaze followed my hoof, but she only saw the rogue cloud. “What is it, Twilight?”

I scowled at the cloud, hoping Rainbow Dash would get the message. “It's probably nothing.” At least, it better be. If Rainbow Dash was spying on my date ... I would need to have a talk with her. A talk she wouldn’t enjoy.

I tried to put the matter out of my mind as one of the waiters led us to our seats. Once Cloud and I were settled into our seats, the restaurant’s staff gently broke our cloud off from the main mass, letting us drift just far enough away from the rest of the tables to give us a little privacy. The waiter then lit a candle set in the middle of our table, then discreetly flew away.

So it was just me and Cloud. Alone. On a date. At a nice restaurant where we were having a romantic candlelit dinner. Meep.

I buried my head in the menu so I wouldn’t need to look at Cloud Kicker for a bit. That quickly led to another discovery: all the food here was really nice gourmet stuff. And most terrifyingly of all, there weren’t prices listed on the menu. Everypony knows that only one kind of restaurant has menus without prices.

I shuffled nervously in my seat. “Cloud, you didn't need to take me someplace this nice.”

Cloud looked up from her menu and smiled. “Sure I did. Anypony I'm taking out on a date deserves the best.”

That just made me feel worse. She was being too nice to me, and it made me wonder why. Suddenly Rainbow’s warnings seemed a bit more realistic. If Cloud was being this nice to me, what was she expecting me to do in return? “You really don't need to go all out on me.” I waved a hoof vaguely. “It’s not like I have any other dating experience to compare this to. I would’ve been fine with just getting some hayburgers.”

Cloud didn’t say anything for a bit. Instead she just reached across the table and took one of my hooves in hers, gently squeezing it. “Hey. Look at me.”

I took a deep breath, then uncertainly met her eyes. “Er, okay then. I’m looking.”

Cloud met my eyes, her expression surprisingly serious. “If I'm gonna date you, I'm gonna make sure you get the best date I can give you. Not because I want anything out of you, but because that's exactly what you deserve. Got it?”

My cheeks warmed up again. “I really don’t ... I’m just ... well I’m just me. Nothing special.”

“Yeah, nothing special at all.” Cloud chuckled and shook her head. “You only graduated at the top of your class from a school for gifted unicorns, wielded the Element of Magic against a whole bunch of crazy monsters, and helped save Equestria three times. Nothing special.” She waved a hoof dismissively. “But none of that is why we’re here. Yeah, you’re just you. And you know what? I like what I see.”

“You're just flattering me...” And judging by how my cheeks felt like they were on fire, it was working.

“No, it's the truth,” Cloud insisted.

That just made me blush even more. “Okay, I guess I can see you thinking that.”

Thankfully, Cloud didn’t press the issue past that. I knew it was biologically impossible for a pony to blush herself to death, but my cheeks seemed determined to prove science wrong. After a couple seconds of silence, my date switched topics. “So, how've you been since the wedding?”

“Oh, I’ve been all right.” I let out a very quiet relieved sigh, happy to be back in safer territory. “I’m glad that my brother and new sister-in-law are doing so well, and that we sorted out all that changeling business. And me ... well, it's just been normal for me for the most part. Soon I’ll just be back in Ponyville running the library, I guess. Hanging out with my friends now and again and just ... well, normal life.”

Cloud cocked her head to the side, scrutinizing me. “Do you like running the library? Because you sounded a little...”

She left the thought unfinished, but I could guess where she’d been going with it. “It's ... all right, I guess. I mean, I love books and reading, so living in a library appeals to me. I’m still not completely done with reading everything in there. It’s just that ... well, being in charge of a library isn't very challenging. Especially not in a small town like Ponyville. I think I could reshelf every book in the library with my eyes closed by this point. I like the time it gives me to read and study, considering I can go hours without seeing anypony, but...” I trailed off, searching for the right words.

“It’s not exactly your dream job?” Cloud suggested.

I sighed and reluctantly nodded. “Being a small-town librarian isn’t very ... rewarding, I guess. I love Ponyville and spending time with my friends, and the library’s an easy job that gives me plenty of time to study, and I love studying almost as much as I love my friends. It’s just that after a certain point you have to wonder if there's something else.” I groaned and ran a hoof down my face, trying to find the right words for it all. “Sooner or later you're supposed to stop studying full-time and actually apply what you know, right? I suppose I technically do that whenever there’s a crisis we need to help Rainbow solve, but—well, that’s not exactly a regular thing. I wanna do something ... bigger than just study all day while I’m waiting for the next crisis.” I looked down at the table, studying it intently. “I ... sometimes I find myself hoping something will go wrong again, just so I’ll be able to help fix it. Because that’s the only time I really feel like I’m using what I’ve learned.”

Cloud gently took my hoof again. “I think I understand. You’ve never really had a chance to apply all the stuff you studied to your day-to-day life.”

“Exactly.” My ears drooped a bit. “I was at the top of my class at the School for Gifted Unicorns, but ... well, Moondancer was the second best student, and she’s running a university research project that could completely change how we look at the amniomorphic spell matrix. And I’m...” I slumped down against the table. “I'm running a little library in a small town. I don't want to sound insulting or unappreciative, but...”

“Kinda feels like you should be doing something better with your life?” Cloud gave my hoof a reassuring pat. “I think I know how you feel, actually. I mean, I went to West Hoof and was pretty close to the top of my class...”

I nodded along, seeing where she was going with this. “And now—no offense—you're pushing clouds every day.”

“Yeah, exactly.” Her shoulders slumped. “It feels like a pretty big waste of four years of education, doesn't it?”

I sighed, starting to feel a little bit depressed now. “Yeah, more than a little bit.”

The two of just sat there in painful silence. After a little bit, the waiter dropped by to take our orders. I got the eggplant parmigiana, while Cloud got a lemon-pepper pasta dish.

Once the waiter stepped away, Cloud’s ears perked up a bit, and she seemed to shake off the bad mood that had been hanging over both of us. “Actually, I've been thinking: you remember how during the whole problem with Sombra, I was in charge of Ponyville's security for a while?”

I hadn’t been there to see it, since I was busy helping Rainbow Dash deal with Sombra, but I’d heard about it. “I remember. What about it?”

“I was just thinking...” Cloud waved a hoof vaguely through the air. “Well, with all the crazy stuff that's been going on lately, maybe that could be a permanent position?”

I blinked in surprise. She certainly had a point about how many strange and dangerous things had happened, but I’d never really considered the idea of having a permanent security pony around. “Maybe. Certainly Ponyville suffers more than its fair share of monster attacks thanks to being next to the Everfree. And the Element Bearers seem to attract the type of attention that could cause more problems for the town.”

“Yeah, exactly.” Cloud shrugged uncertainly. “So, I dunno, it was just an idea, but ... it'd be nice to be able to do a kind of Guard-like thing that still let me stay in Ponyville.”

“It’s not a bad idea,” I tapped my chin thoughtfully. “Maybe you could try talking to Shiny about it? He is Captain of the Royal Guard, after all. If anypony could set that up, it would be him.”

“I could give it a shot.” She paused, then grinned at me. “Well, assuming he’s satisfied with how I treat you tonight. Otherwise...”

I held a hoof over my mouth and giggled. “Otherwise, he’ll by my crazy, protective BBBFF, and you’ll be lucky to make it out of Canterlot in one piece, let alone asking him for a job.” I waited a moment for my giggles to die down, then returned to the more serious conversation. “Though really, I think it would be worth looking into if that's what you want to do with your life.”

Cloud nodded thoughtfully. “I'll think about it.” There was a brief silence, then she turned to me. “So ... what about getting you out of the library?”

I frowned and mulled the question over in my head. “I'm not sure. I've never really thought that far ahead. While I was going to school, I just concentrated from getting to one test to the next and making sure all my assignments were perfect. That I didn't mess up. I'm not sure I've ever had a plan after that.” I shrugged. “Then all the crazy stuff with Nightmare Moon happened right after I graduated, and after that I was mostly happy just spending time with my new friends and getting to know Ponyville. It’s only recently that I’ve started feeling a little ... unsatisfied.”

Cloud’s eyes settled on me. “Well don't you think you should do something about that?”

I sighed, slumping down and staring at the table. “Probably. Now that I'm thinking about it. I think what’s been holding me back is that I'm a bit scared of what is next. Theoretically, I could be comfortable where I'm at. The library job is easy, and I get to be around my friends. The best ponies I've ever known.” I idly poked the table with a hoof. “I'm worried about losing what I have. I mean, there just aren’t going to be very many opportunities for high-level magical research in a small town like Ponyville. If I have to choose between my friends and doing some real academic work...”

Cloud nodded. “I know exactly how you feel. I would be devastated if I lost my friends. That's why I really liked my idea for doing security in Ponyville. It’s ... well it's the best of both worlds.”

“So I guess I need to try to come up with something similar for myself.” I slumped down, tapping my head in an effort to stimulate my brain into coming up with a good idea. It didn’t work. “I suppose I’ll just have to keep an eye out for good opportunities.” I looked over at Cloud, and felt a guilty little twinge. “Sorry if I'm dragging the date down. I know you probably didn’t want to hear me talking about all my silly problems.”

Cloud waved my apology off. “It's fine. To be honest, having a meaningful conversation about where we’re going with our lives is a lot better than the usual date talk I have to put up with. Usually they just want to talk about their friends, family members, exes, or some other group of ponies I’ve never met. Which makes it less of a conversation, and more me listening and faking interest as hard as I can.”

I chuckled softly. “Well you already know all my friends, and my brother’s wedding was the most interesting thing that’s happened lately in my family. As for exes...” I trailed off awkwardly, all too aware of the fact that I didn’t have any exes to talk about. Twilight Sparkle, the dateless wonder. Maybe I should just resign myself to the inevitable and buy a couple dozen cats to keep me company.

With that cheerful thought in mind, I asked the question that had been on my mind ever since this whole mess started. “So... Why did you ask me of all ponies out?”

“To be honest? At first I thought I was just doing it on a whim.”

Oh. So it had been pure impulse. I guess I should’ve known. Except... “At first?”

She nodded. “Yeah, but then I thought about it. I mean, out of all the ponies in Canterlot, I asked you out. And then I remembered how we talked and worked together to deal with the whole Trixie situation. Or the whole thing in Cloudsdale during the Best Young Fliers competition.”

My ears perked up a little. “That is true. We worked together to help Rainbow with both of those problems. I guess I just ... well, I never thought it was anything more than us helping out a mutual friend.”

“Neither did I, at first,” Cloud admitted. “But, well, I kind of got to know you while we were doing all of that. It gave us that initial connection. And I guess I wouldn't mind seeing if anything more can develop out of that. I mean, you're a smart, pretty, interesting mare. We’re both single. Why not give it a shot?”

I felt the corners of my mouth hesitantly twitch upwards. “You mean ... you really want to see where things go? This isn’t just a...” I tried to think of a diplomatic way to ask whether this was a pity date or just part of her plan to win over Rainbow Dash.

Before I could come up with a way to say it, Cloud shook her head. “I asked you out because I wanted to take you out on a date. No other reason. It’s one of my rules.”

My tiny little smile got a little bit bigger. “That’s ... thanks. It’s nice to hear that.” For a moment, I almost managed to believe it. Then reality came crashing back down: even if she wanted to date me, there was somepony else she wanted to date more.

I had to pick my words carefully, since I was pretty sure that pony was spying on our date. I didn’t want to give away a secret Cloud had trusted me with. “Though what about that thing you told me about? At the place? With the pony?”

Cloud stared at me, cocking her head to the side. “Er ... can you narrow that down a bit? Because that could mean ... anything.”

I ran a hoof over my face and tried again. “Remember that talk we had back in Cloudsdale? The one where you told me about somepony else you might have an interest in?” Somepony who I could swear was hiding in a cloud a hundred feet away, watching us through a pair of binoculars.

Comprehension lit up Cloud’s eyes. “Oh!” A moment later her face fell, and she shuffled in her seat. “Er ... right. That.”

“Yes. That.” My eyes dropped down to my hooves. “I ... I understand if you want to pursue her. Instead of me, that is. I mean, she's a lot braver, stronger, more charismatic, better-looking, and more interesting than me. Not to mention you’ve known her for a lot longer than me. So ... really, who could blame you?”

“Hey.” Cloud reached across the table and put one of her hooves on top of mine. “I asked you out. Not her.”

Despite her efforts, my ears drooped further. “Probably just because you didn’t think she’d say yes. Maybe you should have tried, though. I mean, I know she acts tough on the outside, but deep down she’s a very sensitive, caring pony. And there’s no sense settling for something less than what you really want. Who wants to go through life with nothing but regrets?”

Cloud frowned and sharply shook her head. “I'm not 'settling' for anything. I asked you out because I wanted to go on a date with you.”

I groaned and shrank down in my seat, wishing I could just disappear underneath the table. “Sorry, I'm messing this up. Again.”

“Not at all.” She got out of her seat, trotting over to my side and putting a hoof underneath my chin, lifting it up so she could look me in the eye. “I chose you.”

I met her eyes, and slowly started smiling again. “You really mean that?”

“Yeah, I do.” Cloud took a deep breath and nodded to herself. “I mean, she's not interested. Doesn’t see me as anything more than just a friend. That's ... well, it’s not what I wanted, but there’s no point in crying over what I can't have. Especially not when I've got a smart, talented, sexy mare right in front of me.”

I felt my cheeks warming up a bit as my smile widened. “You're so sweet. It's ... nice to be complimented, for once.” I blinked, and hastily amended that. “I mean, my friends say nice things about me too, but ... well, this is different.”

Cloud grinned, and one of her hooves gently brushed my cheek. “I'll make sure to do it more often, then.”

“I think I would like that.” My cheek lit up even further when Cloud touched it. “You're being really nice to me. It’s ... thanks.” A little voice in the back of my head told me that Cloud was probably just being nice to me so I would sleep with her, but I ignored it. In all honesty, a part of me wouldn’t even mind if that was the case. After all, if a pony like Cloud Kicker really found me that attractive ... maybe it was okay? It wasn’t like I wanted to die a virgin, and who knew when I would get another chance?

Cloud removed the hoof and cleared her throat. “So ... I can tell you went all-out for tonight. It looks amazing.”

I giggled nervously. “Noticed, did you?” I cast a mirror spell to give myself a quick check. Fortunately, the flight up to Cloud Nine hadn’t messed up my hair or my dress. “I was worried I was overdoing it. I've never really got this dressed up for something like this. The closest I can think of is Shining’s wedding.”

“Well it looks good,” Cloud assured me. “Real good.”

“You really think so?” I couldn’t help fishing for a couple more compliments. “You can be honest with me, you know.”

“I’m being as honest as Applejack,” Cloud answered confidently. “You look great. Though it’s not just because of the makeup or the dress. Those help, but I think part of it’s also just you. There’s a psychological component to looking good. If you really try to look good and put yourself out there, ponies can pick up on that effort. It’s like ... I can tell you went to a lot of effort to make yourself pretty for me, and that makes me appreciate your appearance even more.”

“Thanks.” I smiled to myself, and for once I managed to do it without blushing. “Good to hear that all the trouble I went to dressing up paid off.”

“Oh yes.” Cloud chuckled and waved a hoof down at herself. “If anything, I actually feel a bit underdressed now.”

I snorted out half of a laugh. “We probably should have coordinated a bit better on that.”

“It's fine,” Cloud waved me off. “I think it's better this way, really.”

“Really? Why do you think that?”

Cloud grinned and leaned back in her chair. “Lemme give you a bit of sage dating advice for when it comes to mares: always make your date feel more beautiful than you.”

I grinned playfully. “So you're saying I should do my best to look worse than you next time?”

She smirked and shook her head. “You’re usually better off making them feel pretty than making yourself ugly. After all, if I’d showed up at your place covered in dirt and grime, you’d think I didn’t care about the date.”

“That’s a good point.” I know Mom and Shining certainly wouldn’t have approved. “Though it helps when you're pretty too. I mean, it took me forever to get everything ready for this, while you probably just needed to brush your mane and put on a nice dress.”

Cloud answered with a relaxed smile. “Trust me, there was a bit more to it than that.”

“Okay, maybe it took you a quarter of the time it took me to get ready.” I self-consciously ran a hoof through my mane. “Without somepony helping me, it takes forever just to get my mane looking good. You have no idea how hard it is to keep all these colors from getting mixed up and looking awful. I don’t know how Rainbow manages to keep her mane looking decent, especially when she doesn’t seem to try at all. It just naturally works out for her.”

“Well, all your hard work paid off.” Cloud leaned forward and slowly ran a hoof through my mane. Her touch lingered around my ear, then slowly worked its way down my jawline and neck. It felt ... nice to have somepony touching me that way, and I found myself unconsciously leaning into the touch more and more. And wondering what it would feel like if she touched me somewhere else.

Then a certain rogue cloud let out a loud rumble of thunder. A rumble that sounded suspiciously like a certain scratchy-voiced pegasus growling, “Stop touching her like that.”

That broke the moment for me, and I turned my head to fix that cloud with the best glower I could manage while I was still feeling just a little giddy from what had just happened. Cloud blinked at my sudden shift, withdrawing her hoof and frowning slightly. “Sorry, was I coming on a little too strong?”

I blinked, then hastily reached across the table and took her hoof. I wanted to put it right back where it had been a minute ago, but that felt a little too bold. I could still hold it, though. “Yes, everything is all right.” I smiled, trying to put Rainbow Dash out of my mind. “I just want you to know that I'm really enjoying tonight, even if it has been a bit bumpy.”

“Glad to hear it.” Cloud grinned and squeezed my hoof. “And first dates are always a little bumpy. We’re still kinda feeling things out, after all.”

Somepony politely cleared their throat behind us, and then the waiter stepped forward, carrying two trays. He swiftly and silently set our food down, then made a quick exit. He could probably tell we were on a date, and didn’t want to disturb us.

The smell of my eggplant parmigiana reached my nostrils, and for a minute I forgot all about the fact that I was on a date. Cloud might be winning over my heart, but right now my stomach was running the show. I bit into the eggplant, enjoying the rich flavor of both it and the pasta as the food rolled over my tongue. “Mmm! No wonder you love this place so much. Not only does it have a great view, the food is...”

Cloud glanced up from her own plate, which she seemed to be enjoying just as much as I was. “Yeah, it’s some of the best stuff I’ve ever had.”

I took a moment to swallow, then grinned at her. “Well, if we based the success of the date on how good the food was...”

Cloud smirked. “Yeah, if that was the case I'd have your brother chasing me down Canterlot's streets with a baseball bat.”

I chuckled at the mental image, though I suspect Shining would actually be using one of his old Guard spears. “Probably. He's always been very protective of me.”

“It’s a big brother thing,” Cloud answered confidently.

“So I hear.” My ears drooped a little as I continued, “And, well, I probably needed it after what happened during my admissions test.”

Cloud paused halfway to taking another forkful of her pasta. “Oh. Right. That. Um ... do you mind if I...? Well, I’ve heard what happened, but...”

“You want the first-hoof account?” When she nodded, I sighed, took a deep breath, and dug up those painful memories once more. “When I was doing my admissions test at Celestia’s School for Gifted Unicorns, something went wrong. I had a wild magic surge that went completely out of control. It took half the School’s staff to finally get me under control.” My ears drooped and I slumped down in my seat. “Ponies got hurt because of me. Because I couldn’t control my own magic.”

Cloud reached over and gently squeezed my shoulder. “It wasn’t your fault. You were just a kid, Twilight.”

I let out a bitter, humorless laugh. “A lot of ponies said that afterwards. My parents. Shining. The teachers at school. Therapists. It’s easy to tell somepony that it wasn’t their fault. Making them believe it is something else.” I sighed and waved hoof through the air. “It’s why I never really had any friends until ... well, Rainbow and the Elements. I was always afraid my magic would go wild again and hurt somepony. For more than a month after The Incident, I was too scared to even cast a simple levitation spell.”

She gently tipped my chin up. “Well it looks like you have your magic under control now. I mean, Rainbow always says you’re one of the best unicorns she’s ever seen.”

“Rainbow’s biased,” I said with a small chuckle. “But ... yes. I guess I did work it all out. But there’s still times when I worry something will go wrong again. And ... yeah, since I was such a mess Shining felt like he had to keep me sheltered.” My ears drooped further. “Or maybe he was just afraid I’d end up hurting somepony.”

Cloud flinched sympathetically, her mouth opening and closing several times as she tried to think of some magic words to make me feel better. There weren’t any. “Twilight...”

I cleared my throat and hastily changed the subject before I could drag our date any further down than I was already. “But yes, big brothers. I suppose that's nothing you have to worry about, is it?”

“Nope,” Cloud answered, her ears perking up at the change of subject. “I’m the older sibling in my family. I guess that means I can look forward to when Alula will be old enough for me to start chasing would-be suitors away. I’m already keeping an eye on Pipsqueak. After all, little ‘Lula can’t mention him without talking about what a dummy he is, so I’m pretty sure she likes him.” Cloud chuckled and shook her head. “Kids.”

I wasn’t sure I understood how Cloud concluded that Alula must like Pipsqueak on the basis on constantly insulting him, but since meeting Rainbow I’d learned that a lot of friendships could be strange that way. After all, Rainbow poked fun at Applejack and Cloud all the time, and it only seemed to make their friendship stronger. Though I had to wonder if Pip understood it any better than I did. “Sounds like he's going to have a rough time of it.”

“Oh yes,” Cloud declared with a downright devilish grin. “I shall be utterly merciless if he tries to ask her out.”

I giggled and teasingly swatted her on the shoulder. “Aww, come on, he's a nice little colt. He’s going to be scared enough of Alula, you don’t need to make it worse.”

“Yes I do,” Cloud answered matter-of-factly. “It’s part of the older sibling rules. Just like how I’m nice, but Shining Armor still needed to threaten me.”

I answered with a flat look. “I’m not saying you’re not nice, but your brand of niceness is the sort that big brothers should be worried about. But in any case, I know you could be reasonable with Pipsqueak.” I smirked at her. “The real question is, will you be reasonable?”

Cloud answered my smirk with one of her own. “Mostly. I reserve the right to traumatize him a little. It’s part of the older sibling’s inherent rights. Seriously, one of the entries in the Equestrian Bill of Rights is ‘The right of elder siblings to torment and threaten the suitors of their younger siblings shall not be abridged or restricted in any way.’”

I shook my head. “We both know you’re just making that up.”

“Ask your brother,” Cloud suggested. “He’ll back me up.”

“Of course he would.” I chuckled, thinking back to what he’d said before we left. “Hopefully he doesn't make things too tough on you.”

“I think he’ll probably be reasonable as long as I keep you happy,” Cloud assured me. “Not to say he’ll give me a free ride just because you like me; he’ll probably be tougher than I'd like, but not as tough as he feels I deserve.”

“I guess that’s a reasonable compromise, all things considered.” I grinned across the table at her. “Though I wonder if I should stop talking about my big, scary, overprotective brother before the idea scares you off.”

Cloud waved that suggestion away. “Nah, Shining Armor’s cool. Besides, I've handled way worse than protective big brothers.”

I lifted a single eyebrow. “Dare I even ask?”

“That depends. How many of the sordid details of my love life did you want to know?”

I was tempted to ask for a few. I’ve always been too curious for my own good. After a long mental struggle, my good sense lost the battle. “Maybe just one or two highlights...”

Cloud grinned. “Well, there was this one time when...”

After some interesting dinner conversation and a rather lovely meal, my date with Cloud Kicker was over. Not that I would have minded it going on for a bit longer. Dating was a lot more fun than I’d expected—I’d been worried that I would have to constantly watch everything I said or did to avoid upsetting her. And ... well, a part of me had also shared Rainbow’s concerns that Cloud might be pushy about the physical side of things. Thankfully, neither of those things had happened; Cloud had been surprisingly easy to talk to, and the few physical things she did with me were all surprisingly nice.

Rainbow, or rather the inconspicuous rogue cloud which I was almost certain Rainbow Dash was hiding within, continued following us on the walk home. Clearly Rainbow wouldn’t be satisfied until she saw me home with my virginity firmly intact. A part of me wondered if she really cared about protecting me or if she was just jealous. Though maybe I only suspected jealousy because I knew Cloud liked her, even if it seemed Cloud was moving on now. Confirmation bias might be coloring my perception of Rainbow’s actions.

A sudden, ice-cold breeze swirled down the street. I couldn’t help but suspect that Rainbow might have been behind that. Maybe she was hoping that if the weather was uncomfortable we would hurry home and end the date faster.

If that was her plan, it backfired spectacularly. Cloud noticed me shivering from the cold, and lifted one of her wings for me. I hesitated for a moment, but her wing did look very warm and comfortable, and I trusted her not to use this as an excuse to immediately start groping my butt. Especially not when we were close enough to my home that Shining might see it.

I stepped next to Cloud and tucked that wing over my back, wrapping it over me like a big, feathery blanket. While she didn’t exactly pull me closer to her, I found myself drawn in until our sides were pressing against one another. I certainly didn’t mind that, since she felt very warm and the weather was on the chilly side of things.

Just to make things worse for Rainbow, we also started walking down the street more slowly. It’s hard to move fast when you have another pony’s wing around you. The cloud let out another rumble of thunder that sounded suspiciously like Rainbow growling in frustration.

I did my best to ignore my friend, focusing on my date instead. I pointedly directed my gaze down at the wing around my shoulders, then grinned playfully at my date. “Yes, yes, you're getting to wrap a wing around me. I’m sure you’re enjoying that.”

Cloud answered my smile in kind, gently squeezing me with that wing. “Yeah, I am. And you seem to like it too.”

I couldn’t really deny that when I was all but snuggling against her. “Is there a reason why I shouldn't like it?

“I can’t think of one,” she shot back.

“Then it looks like we both agree.” The two of us walked along in companionable silence after that, just enjoying each other’s company. After what felt like far too little time, we arrived in front of my family home. I reluctantly stepped out from underneath her wing, wondering if Shining was watching us and glaring like the overprotective big brother he was.

I glanced back at Cloud again, and for the twentieth time since the date started, I felt my cheeks warming up. “This has been really nice, by the way.” I hesitated, and the blushing got worse as I struggled to squeak out, “I—I think I might like doing this again. If you wouldn’t mind doing that, I mean. You probably have other plans or something, but—”

Cloud very gently cut me off by placing a hoof over my lips. “I’m free next Saturday. And considering how nice tonight was, I’ll make time for you. But for now, I’ll just say thanks for a lovely evening...”

Her hoof moved away from my lips, cupping my cheek instead. Then she started leaning in closer, and her lips pursed.

She was going to kiss me!

As my lips slowly pursed in preparation, I realized something equally shocking. I wanted to kiss her too. After all, it had been a nice date, and she’d been a perfect gentlemare the whole time. Kissing her goodnight just seemed like the natural way to end the evening. I closed my eyes and slowly leaned forward, wondering what it would feel like when it finally happened. My first kiss.

However, seconds before our lips would have met, the rogue cloud zipped through the sky, placing itself directly over Cloud’s head. There was a loud rumble and then a sudden, massive clap of thunder, and localized downpour hit my date, utterly soaking her in the space of a single heartbeat. We both froze in complete shock, and the moment was completely ruined.

Cloud got the worst of it by far, but I suffered as well. With as close as I’d been to her, it was impossible for her to get drenched while I remained completely dry. My dress was spared too much water damage, but my mane was utterly drenched and I could feel my makeup running down my face. I didn’t even want to imagine what I must have looked like.

And then I looked up and spotted Rainbow Dash’s head sticking out of the cloud. One hoof was over her mouth, and her eyes were guiltily flicking between the two of us. It reminded me of the way Sweetie Belle looked after she’d messed up one of Rarity’s dresses—like she knew she’d crossed a line, but had no idea how to fix it.

I certainly wasn’t inclined to show her any mercy. “Rainbow Dash!” I shouted, my teeth grinding. “You come down here right this minute!”

My yelling snapped her out of that guilty stupor. “Oh horseapples!” She shot out of the cloud, trying to flee the area and escape my righteous wrath.

I wasn’t having any of that. Not after she’d rained on me right when I was about to get my first kiss. Well, my first real kiss. I concentrated, my horn lit up, and a violet sphere encased everything within two blocks of my home.

Rainbow was going too fast to stop in time, and slammed into the shield hard enough that if I hadn’t been so mad I might have felt sorry for her. Then she slowly slid down the shield with a loud, unpleasant squeal. I stalked over to her, trying to get my sodden mane out of my eyes and do something about all the makeup running down my face. That erased any sympathy I might have felt for her. “What the hay do you think you're doing, Rainbow?!”

Rainbow groaned and slowly picked herself up off the sidewalk, turning nervously to face me and smiling sheepishly. “Uh ... hey, Twilight. Imagine us running into each other! What a crazy random happenstance!” When my only response was to glare furiously at her, she nervously rubbed the back of her head. “So ... uh ... what’s up?”

“I think you know what's up,” I growled, stomping over and jabbing her in the chest. “Don’t try to play dumb with me. I know you’ve been following me all night! Did you think I didn’t? Do you think I'm so stupid you could fool me by pretending to be a bucking cloud?!”

Rainbow flinched back, and her eyes widened when I cursed at her. To be honest, I was a little shocked that I’d done that as well. But considering the circumstances, it felt quite appropriate. To be honest, I was tempted to curse her in a slightly more literal sense. “What is wrong with you?! Why did you sabotage my first date ever?!”

“I wasn't sabotaging it,” Rainbow protested, her eyes guiltily flicking over my sodden face and mane. “I was just ... I was trying to...” Her eyes darted back and forth, as if she were looking for an escape route. I didn’t give her one. “Okay, the rainshower was kinda not cool, but I was ... well I had to do something! Cloud was gonna kiss you!”

One of my ears started twitching madly, and I suddenly remembered a prank spell I’d read about that reversed the positions of a pony’s face and rump. “Yes, I noticed that. Good to know you saw it too.”

“Yeah.” Rainbow shuffled her hooves, looking between myself and Cloud. “I mean, I couldn’t let her take advantage of you like that.”

“T-take advantage of me?” I sputtered incredulously. It took a moment for me to get over my shock and remember that I was supposed to be angry with her. “What makes you think she was doing that? Did it never even occur to you that maybe I wanted her to kiss me?”

Rainbow tilted her head to the side, as if I’d suddenly started speaking in Ancient Unicornian. “Whaaat?! But ... that can’t be right!”

“You heard me,” I snapped at her. “Maybe I wanted her to kiss me. But I'm not sure what I want really factored into your decisions.”

“But ... but you can't!” Rainbow sputtered indignantly.

“Why not?” I demanded, glaring down at her. “Give me one good reason why not!”

Rainbow squirmed uncomfortably, her mouth opening and closing several times as she struggled to come up with a good answer. Finally, she just blurted out, “Because!”

“That's not good enough!” I growled, stomping down hard on the cobblestones. “I know you somehow got it into your head that you needed to protect me,” Assuming that wasn’t just a cover for possible jealousy, I silently added, “but did you ever think to ask if I wanted your help?”

Rainbow slumped down further, looking like she wanted to just curl up, put her wings over her head, and try to disappear. “Um...”

“That's right, you didn't.” I angrily turned my back on her. “Because you didn't think I was strong enough to handle this by myself, did you? You thought that ... that I would make nothing but bad decisions.”

“That's not what I thought at all!” Rainbow protested

“Then explain it to me,” I growled, looking over my shoulder at her. “Why did you think you needed to spend the entire evening stalking me?”

“I wasn’t stalking!” Rainbow complained. “I was just ... y’know, following you. Stealthily. And watching you so I’d be there to help if anything went wrong.”

I snorted and rolled my eyes. “Following somepony around and secretly watching them is practically the dictionary definition of stalking.” I summoned the dictionary from my bedroom, opened it up to the appropriate page, and then shoved the book into her face. “See! Right there in the dictionary!”

Rainbow wilted down even further, groaning and covering her eyes with her hooves. Her voice came out as a tiny, miserably whimper. “I ... I was just trying to ... m’sorry, okay?”

I sighed and shook my head. “Right. But you know what? I'm more than old enough to make my own decisions. If I want to kiss Cloud Kicker...” I trotted over to her, taking a moment to appreciate the way that being soaking wet just made her mane hang loose and wild, and how the water had turned her clingy red dress even clingier, hugging to her curves in a way that made her look even more naked than when she was actually naked.

And then I kissed her.

It was nice. Kind of cold and wet, since we were both still soaking wet from Rainbow’s impromptu rainshower. But her lips were still warm and soft. And ... well, nice.

After holding it for a moment I slowly broke the kiss, smiling at Cloud. Then I turned to Rainbow Dash. “See? I kissed her, and the world didn't end.”

Rainbow groaned loudly, covering her face to protect herself from … whatever was going through her head. She can be a surprisingly complicated pony sometimes. “Okay, okay, I get it. I thought that since you were so frag—” She caught herself and quickly reversed course. “Well, I thought ... y’know, I just wanted to make sure you’d be okay. With stuff.”

She sighed, refusing to look at either one of us. “But ... yeah. I guess if you’re alright with it, and Cloud’s making you happy and treating you right, well ... I’d be a pretty sucky friend if I wasn’t okay with you two being happy.” She finally looked us both in the eye, and a hint of the confident trickster I knew so well came back. “All right, so I won’t be a pain in the flank about you two dating. On one condition: could you at least not get all ... couple-y? Watching you guys kiss is bad enough, but if you two start calling each other ‘Schmoopy’ or ‘love muffin’ I’m gonna hurl.”

Cloud rolled her eyes, then one of her wings gently whapped Rainbow upside the head. “Quiet, you. Since you were just being your normal weird, short-sighted, but ultimately well-intentioned self, I’ll forgive you. But you’re not out of the doghouse yet.”

I nodded along with Cloud. “Maybe if you did something nice for us...” I trailed off as the full implications of what I’d just done started to sink in. My cheeks lit up so brightly that any water on them probably boiled away in an instant. “I ... oh Celestia, I just did that, didn't I?”

Cloud smiled and nuzzled me. “You sure did.”

I chuckled nervously, but smiled back. “Yeah, I really did.” I very hesitantly nuzzled her back. “It was ... nice.”

“Nice, huh?” Cloud grinned and teasingly bumped my hip with hers. “Are you sure you can say kissing is nice after just a single experience? After all, that’s a very small sample size. I think we need to collect more data in order to decisively confirm that hypothesis.”

“That seems like a reasonable proposition,” I agreed. “So, see you next Saturday?”

“It’s a date.”

Author's Note

Special thanks to Trinary for letting me play around in his universe. It was rather fun to write a Twilight that's even more neurotic and messed up than her canon version.

As always, thanks to my pre-reading and editing team for all their hard work. Also, I would like to thank all my dedicated Patreon supporters. You guys are awesome.

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