Prompt:
>"Hey uhh... Anon? Can I ask you a question?"
yea? can you? Are you able to?
>"Ughh. I mean, MAY I ask you a question?"
Sure Twiggles, whats on your mind?
>"Well... I was wondering something... Uhh. I don't know how to ask this... Oh shoot, I don't know how to even start. I mean what if you think I'm a weirdo or something and-"
Twilight, nothing you can say will make me think you're a weirdo.
>"Nothing? Are you so sure Anon?"
Ok. So maybe a few things, but the chances of you saying them are pretty low. So ask away.
>Twilight starts to hesitate again, but takes a deep breath and begins to ask her question.
>"Is there something wrong with me?"
What? What are you talking about?
>"I mean like... How I look?"
No... you seem normal to me. What do you mean?
>"Well... I don't know if you've noticed but... around this time every year, everyone's running around finding dates for Hearts and Hooves day. "
Oh...
>"yea.... well. I...I-I just was kinda wondering... Why nobody ever asks me?"
>Twilight refuses to look at you, her eyes are glued to the floor as she nervously fiddles with her hooves.
>"Am...A-am I. Ugly?"
>You begin to hear her voice falter. Its obvious she's getting more emotional than she anticipated.
No! of course not! There has to be another explanation. Maybe its because you're a princess? Maybe thats intimidating to some people. Hell... I don't know.
>You scratch your head, not knowing what to say to her.
>"Do...do you think I'm ugly?"
>You bend down and gently rub her mane. She looks up at you for your answer.
No Twilight. Of course not. I think you're a cute little pony.
>"Cute? m-me?"
Yea. Whoever gets you will be one lucky stallion.
>She tries to hide her blush, but she's doing a terrible job of it.
>"Do you think...umm. Do you think...If nobody asks me...uhh"
>She takes another deep breath, trying to draw in courage.
>"Do-you-kinda-wanna-maybe-go-out-with-me-for-hearts-and-hooves-day-or-something!?"
 
Response:
"Sure, I would love to!"
>The words left your mouth without forethought.
>"Really Anon? You will? YESOHYESOHYES!"
>What the fuck did you just get yourself into?
>Twilight was starting to get into one of her classic panic attacks.
>You knew better than to stick around during one of those.
"Ok, so I'll uh, see you then Twilight."
>Twilight didn't even respond as you walked out the door of her library, she just continued her episode.
 
>You hadn't gotten three steps out away from the door before you bumped into Rarity. Literally.
>"Oh, my apologies Anonymous. I didn't see you there."
"Thats a new one. Aren't I like, huge compared to you ponies? How can you possibly miss me?"
>"I was just, um, thinking about something."
"Let me guess, you're worried about Twilight."
>Rarity looked stunned. You knew you had guessed correctly.
"Well you can do both of us a favor, she's in there having one of her episodes."
>"What did you say to her?" Rarity demanded.
"Only that I would join her for Hearts and Hooves day."
>"You WHAT?" A new voice called out.
>Oh shit, its Lyra.
>She was carrying a box of chocolates on her back.
"Sorry Rarity, gotta run!"
>You took full advantage of their surprise as you booked it in the direction of town.
>"Oh no you don't!" Lyra yelled as she chased after you.
 
>It took you almost an hour of running in circles, but you had finally lost Lyra.
>You couldn't have done it alone, thankfully along the way Pinkie Pie decided joining in would be fun.
>She helped you hide in a back room of Sugarcube Corner.
>After releasing you once the coast was clear, she sat down at a table with you and some cupcakes.
>"So Nonny, why were you running from Lyra?" Pinkie asked while popping cupcakes into her mouth.
"Lyra may have thought that I would take her out for Hearts and Hooves day, but she overheard me saying that I'm taking Twilight."
>"You're taking Twilight out for Hearts and Hooves day? Aww thats so sweet."
>Pinkie was smiling at you through a mouthful of cupcake.
>"But I thought you didn't want to date anypony." She added looking a bit confused.
"I don't know, it just sort of happened! Twilight was acting all weird and before I knew it, I agreed to the date."
>Pinkie laughed really hard. So hard in fact, that she got bits of cupcake all over your suit.
"Don't laugh Pinkie, I'm really worried here. First I agree to date Twilight, now I have to worry about Lyra stalking me."
>After Pinkie finally managed to stop laughing, she spoke again.
>"That just means you're popular, silly!"
>You just sigh.
"I don't really want to be popular with mares."
 
>Since Pinkie Pie could tell you were in a bad mood, she spent the rest of lunch trying to cheer you up.
>As cheesy as her jokes were, they did eventually put a little smile on your face.
>You still didn't like the situation you were in, but atleast you felt a bit better.
>As you leave Sugarcube Corner, you see a very distressed looking Applejack.
>Against your better judgement, you approach her.
>"Applebloom, when Ah find you, Ah'm gunna make ya wish you never crossed me."
"Applejack?"
>"Oh, Anon! Thank Celestia you're here. Can you help me clean up this mess?"
>She points a hoof at a bunch of apples lying all over the ground.
"Sure, I'll help."
>'Not like I have anything better to do' you think to yourself as you start picking up apples.
"So what happened here?"
>"Applebloom was supposed to help me deliver these apples to Sugar Cube Corner, but she ran off with her friends."
>"Then Ah tripped 'cuz Ah was trying to carry too much."
"Well Sugarcube Corner is pretty close, so I can help you carry these."
>"Thanks Anon, yer a real gentlecolt."
"Gentleman." You corrected under your breath as you helped Applejack.
 
>A few minutes later the task at hand was finished.
>You were about to leave, but you stopped as you felt a tug from behind you.
>"Wait Anon, there's actually something I need to ask you."
>It was Applejack who stopped you.
"What is it?"
>"Ah was wonderin' if you had plans for Hearts and Hooves day." Applejack practically stammered out.
>You both froze as the words came out of her mouth.
>You didn't see this one coming.
>Applejack was always friendly, but you never expected her to actually ask you out.
>This day just got weirder and weirder.
"I'm sorry Applejack, I already have plans."
>Her ears drooped and she looked at you with the saddest eyes you have ever seen.
>"What... What kind of plans?" She asked, tearing up.
"I already promised I would go with Twilight. Again, I'm sorry, I really am."
>For the first time you had ever seen, Applejack started openly crying.
>You took this as your queue to leave, as nothing you said could really comfort her at this point.
 
>You aimlessly walked around Ponyville, trying to distance yourself from Sugarcube Corner and the sobbing mare.
>You didn't get far before there was a rainbow-colored flash, and you found yourself flat on the ground.
"Goddamn it Rainbow Dash, not again!"
>"Sorry about the rough landing, but I needed to talk to you."
"Don't tell me you want to ask me about Hearts and Hooves day too."
>"No, of course not. I like mares, Anon."
>Well that explains alot.
>"I wanted to ask if you knew why Applejack was crying uncontrollably while saying your name."
"Oh."
>"So what happened?"
>You explained to Rainbow Dash everything that happened since Twilight asked you to be her date.
>"Okay, I think I got it." She said, as you got to the part about Applejack.
"So what do I do now?"
>"I'll go back and do what I can to comfort Applejack. It sounds like you need to talk to Lyra."
"Ugh, but avoiding her is so much easier."
>"You can't avoid her forever, Anon." Rainbow Dash answered before taking off.
"Watch me."
 
>You were quickly forced to eat your words.
>When you turned around, you were greeted by a smile that terrified you.
>It was Lyra, lying sideways on a bench, with the heart-shaped box of chocolates held in front of her chest.
>"Found you."
>You thought about running again, but saw Pinkie Pie staring at you from a nearby alleyway.
>The look she was giving you told you running wasn't an option this time.
"Look Lyra, we need to talk. I know you-"
>"Yes, we certainly do need to talk." She interrupted.
>"I had been making plans to ask you out for Hearts and Hooves day for months, Anon! Months!"
>"But you go and make plans with Twilight Sparkle on a whim."
"Lyra, listen, I-"
>"No, YOU listen!" She spat back.
>"I've been trying to get you to notice me ever since you came to Ponyville!"
>"I've tried so very, very hard, but you never seem to care."
>"WHY WON'T YOU CARE?"
>As she shouted those words, she threw the box of chocolates in your face.
"Lyra I do care about you, but not in that way. I just wanted to be friends."
>"I was okay with that when you said that you didn't want a special somepony, but now you agreed to date Twilight!"
>"Where does that leave me?"
>You didn't have a good answer. You just dropped your gaze to look at the ground.
>"Won't you atleast consider choosing me over that boring purple mare?"
>For a moment, you did consider it, but you had already made your decision.
"I'm sorry Lyra, but I can't do that."
"I won't break my word with Twilight, and I won't let you guilt trip me into dating you."
>It hurt to say these words. You had never been good at this sort of thing.
"Goodbye, Lyra."
>And once again, you left having broken another mare's heart.
>Not wanting to deal with any more drama, you head straight home to your cottage outside Ponyville.
>After a quick dinner consisting of leftovers, you decide to get some extra sleep.
>It had certainly been a crazy day.
 
>The following morning you were awoken by violent knocking on the door to your cottage.
>After putting some clothes on, you answered the door.
>Standing at your door was Big Mac, and he was staring at you angrily.
>You could guess why.
"G-good morning." You stammered out, trying not to meet his gaze.
>"I have a few questions for you, Anon." Big Mac said, continuing his angry glare.
"Okay, come right in."
>You were trying to be nice, but you couldn't help but be a little nervous.
>Big Mac almost never showed any anger, yet everyone knew he could be scary when he wanted to.
>This was one of those times.
>"Okay Anon, I'm not here to threaten you or anything."
"Oh thank God. You looked upset and it was making me nervous."
>"Eeyup. I'm here to deliver a message from Applejack."
>"She said she doesn't want what happened yesterday to ruin your friendship, but she isn't quite ready to talk to you herself."
"I see." You replied, taking a seat in your small living room.
>Big Mac followed your example, and took a seat on the floor nearby.
>You two just sat there silently for a few moments before Big Mac spoke again.
>"You sure you don't got nothing else to say?"
"Not really. What else do I say to a mare after I break her heart?"
>"No." Big Mac shook his head. "Not that. You sure you don't want some help with Twilight?"
>You blinked. You hadn't expected him to say that.
"You would do that? After what I just did to your sister?"
>"Eeyup."
"Thanks Big Mac, you're such a bro."
>"Eeyup."
"Alright, where to start..."
>You took a deep breath and explained what a crazy day you had yesterday.
 
>Be a certain purple princess pony
>A pony who now had a date tomorrow!
>You couldn't help but be really excited, but you were equally nervous.
>You had never been on a date before.
>There were all sorts of books on dating in your library, but none of them said anything about human stallions.
>You weren't sure how much would be the same, or what would be different.
>While you were reading as much on the subject as you could, you heard a familiar knock on your library door.
"Come in."
>The door opened with magic, and Rarity walked in.
>"Your date is tomorrow Dear, what are you doing still reading?"
"That's why I'm reading! I'm reading about dating."
>Rarity let out a soft chuckle.
>"Oh, Twilight. What will I ever do with you."
>She pulled the book you were reading out of your hooves with magic, and set it on a nearby table.
"Hey, what are you doing? Give that back!"
>"Come along Twilight, you have much to learn, and none of it will be in those books of yours."
>You knew Rarity was right, so you sighed and followed her as you both walked out the front door.
>After telling Spike goodbye, Rarity led you into Ponyville.
>One short walk later, you arrived at the Ponyville Spa.
"Wait, why are you taking me to the spa, Rarity?"
>"We need you to look your best for tomorrow, of course."
>That makes sense.
>"And.. well, there isn't a better place in all of Ponyville for gossip!"
>You let a grin show on your face.
"So that's your real angle."
>Rarity smiled back at you.
>"Oh dear, was it that obvious?"
>You both giggled as you walked inside and were seated for your group massage.
>Rarity wasted no time getting to the topic at hand, and before long you were both gossiping about Anon and your date tomorrow.
>For the next few hours, you were thoroughly pampered.
>First Aloe and Lotus gave you a message, then you had a long bath, and finally Rarity helped you choose a dress and showed you how to use makeup.
>The afternoon passed by very quickly, and soon it was sunset.
>You were about to return home, but Rarity stopped you one last time.
>"Now Twilight, I want you to repeat to me what I told you about tomorrow."
>You smiled, confident in your perfect memorization skills.
"Number one, let Anon lead since he is the stallion. Two, don't let him do all the talking. Three and most importantly, I have to try not to be nervous!"
>Rarity nodded her head, and gently put a hoof on your shoulder.
>"And you're sure you can do all that, Dear?"
>That little comment made the reality of the situation hit you like a brick wall.
>You weren't sure how to answer, but you caught sight of yourself in one of Rarity's many mirrors.
>You didn't normally like to complement your own appearance, but you looked absolutely stunning.
>Your dress was made of purple silk, with sequins spaced all over.
>Even the smallest movement made light dance across your body.
>With newly inspired confidence, you looked back at Rarity and nodded once.
>"Well good luck tomorrow. I've done all I can to help, the rest is up to you."
"I know, and thank you again Rarity."
>You hummed a happy tune as you walked back in the golden light of the sunset.
>Tomorrow was going to be a great day!
 
 
>Be Anonymous
>You had spent more time than you liked to admit getting ready.
>You were wearing your finest suit and tie.
>You had picked up some flowers and a box of chocolates.
>You were more than prepared, yet you couldn't help but feel a bit nervous as you knocked on the door to the town library.
>A few tense moments of silence passed before you heard footsteps from inside, coming for the door.
>When the door opened, you were greeted by a tiny purple dragon.
>"Hey there Anon, you're early."
>Early huh? You were never good at telling time.
>Ever since your watch stopped working, you've been having to guess the time based on the position of the Sun.
>You really should get it fixed.
>Oh well, it was better to be early than late.
"Sup Spike, is Twilight ready yet?"
>He shook his head.
>"No, not yet Anon, but I can tell her you're here."
"Okay, I'll just wait out here."
>Spike nodded and ran off to talk to Twilight.
>You didn't have to wait long.
>Soon after Spike went back inside, you heard Twilight's muffled voice and lots of footsteps.
>After about a minute, the door opened again and before you stood a very well-dressed Twilight Sparkle.
>She had her mane very carefully braided, and was wearing quite a bit of makeup.
>You weren't an expert but you thought it was a bit too much.
>But the dress! Oh, the dress was amazing!
>It was a slightly brighter purple than her regular fur, but it was made of fine silk, and it sparkled in the light as she moved.
>Usually you didn't care much for Rarity's dresses, but she had outdone herself this time.
"Wow, you look..."
>You took a moment to collect your thoughts before finishing the sentence.
"Stunning."
>That one word made Twilight blush so much it was visible though all the makeup
>"Thanks, Rarity helped me choose the dress."
"And she did a great job. Here, you might want to leave these here."
>You handed her the flowers and chocolates.
>"Thank you Anon. Does this mean humans do give chocolates on Hearts and Hooves day too?"
>She levitated your gifts inside as you explained how humans had a similar holiday.
>Before long, you two were on your way through Ponyville.
>"And that's why Hearts and Hooves day was created!"
>You hadn't been prepared for Twilight to explain the entire reason for the holiday, but it was atleast somewhat interesting.
>Thankfully your first stop was coming up, now you could change the subject.
"Ah here we are, the local cafe."
>You and Twilight sat down at one of the outside tables.
>Twilight started looking nervous as she noticed how many other couples were there too.
"Such a gorgous day! I guess it's no wonder this cafe would be busy." You say, trying to ease Twilight's nerves.
>She smiles back.
>"Well, of course it is. The weatherponies wouldn't let it rain on a holiday!"
"I guess not. Honestly, Im still not used to the whole manually controlling the weather thing."
>"Yes, you've told me a few times that Humans were unable to control the weather like ponies do."
"So while we wait to order, why don't you tell me what you've been up to this week?"
>"I helped Applejack move some supplies across Ponyville, and on Tuesday afternoon I had tea with Rarity and Fluttershy."
"And I assume alot of the remaining time was spent reading?"
>"..Yes." She admitted, her gaze faltering a bit.
"Hahah, I expected no less of the brilliant Twilight Sparkle."
>It was then the waiter approached your table.
>"Hello Anon and Miss Sparkle, can I get your order?"
>You turn to face the waiter and answer and before you stands none other than Discord himself in a tuxedo, holding a notepad.
"Discord? What are you doing here?"
>"Why I'm simply volunteering my services as a waiter temporarily. This cafe is always terribly short on extra help on the holidays."
>You didn't buy that story one bit.
>Discord may have improved his behaviour, but he still often had ulterior motives.
>Though these days his goals were more about quick laughs.
"What's the real reason, Discord?" You asked, glaring straight at the draconequus.
>"Why I heard from a little birdy that you and Twilight were on a date, and I just HAD to see that."
>He laughed at you both long enough for Twilight to turn a bright red again, and cover her face with her hooves.
>Before you could chew him out for making Twilight uncomfortable though, he changed his focus to something in the nearby bushes.
>Whatever it was, it was making him visibly nervous.
"Discord? You alright there?"
>"Well, it was nice seeing you two, have a nice date, gotta run!"
>With a snap of his fingers, he was gone, and before you there were suddenly two salads on the table.
"Well atleast he was generous enough to leave us some salad."
>"Yeah. I wonder who told him we had a date today? I only told Rarity and Spike." Twilight pondered, grabing her salad.
>Returning your attention her way, you had to stifle a laugh.
>She had smudged her makeup pretty badly with her hooves.
>While it was pretty adorable at the moment, you should probably tell her.
>You take a deep breath and attempt to inform her calmly.
"Twilight, you might want to take a trip to the mare's room." You wisper in her ear.
>"Why? What's wrong Anon?"
"Just trust me and go look in a mirror."
>She nodded and walked to the bathroom.
>You quietly sat alone at your table and ate your salad while you waited for her to return.
>After about fifteen minutes though, you start to get worried.
>You walk over to the door of the bathroom and knock on the door.
"Twilight? You okay in there?"
>You heard some muffled sounds from inside, before the door suddenly shot open and Twilight dragged you inside.
>Suddenly you were pulled down to face level with Twilight and you stared right into her tear filled eyes.
>"Anon, tell me the truth. Did you go on this date with me out of pity?"
"What? No! Why would you think that, Twilight?"
>"Because you've told me several times you didn't want to date anypony."
"Well.. Yes, I did say that once, but that was a long time ago."
>You carefully wipe the tears from Twilight's face.
"Listen to me Twilight, and listen carefully."
"I certainly wasn't expecting you to ask me out for Hearts and Hooves day, and back then I never expected us to actually go on a date together."
"But here I am, on a date with none other than the Princess of Friendship. I wouldn't give it up for-."
>Twilight grew closer and closer as you spoke, and before you could finish, she pushed her face onto yours in a passionate kiss.
>Surprised as you were, this didn't stop you from enjoying it.
>You wrapped your arms behind Twilight, drawing her even closer.
>You felt her fur rubbing against your skin, her warmth against your body.
>Her wings awkwardly flapped about in the tight confines of the bathroom, pushing up against the walls.
>The kiss probably only lasted a few seconds, but it felt so much longer.
>Once she pulled away, you only had one thing to say.
"I love you, Twilight."
 
>Several hours later.
>You were thankful that Twilight knew an invisibility spell, or you might have started some rumors around Ponyville when you exited the cafe restroom.
>After that, you took Twilight back to her library so she could properly clean up her makeup.
>Then the two of you just sat and talked for a bit, but you told her to keep an eye on the window.
>At sunset, you led her back outside again.
>"So where are we going this time, Anon?"
"You trust me right?"
>"Yeah, I trust you." She answered with a smile.
"Then just follow me. I promise you'll love it."
>You led her out of town, in the direction of Fluttershy's cottage.
>Once you got near however, you suddenly stop and face Twilight.
"Okay Twilight, we just have to cross through this initial thicket here, then we'll be there."
>"We're going into the Everfree?" She asked, obviously confused.
"Yes, but not far. Fluttershy showed me this spot. It's perfectly safe."
>"Okay."
>Holding Twilight by one of her wings, you guide her along the narrow path into the Everfree.
>It takes less than five minutes to reach your destination.
>The path opens up into a meadow, with all kinds of flowers and small plants.
>During the day, you would be able to see all their bright colors, but it was now getting dark.
"Here we are, my Princess."
>"It's gorgeous! I can see why you brought us here."
"Now now, I didn't just bring you here to show you the meadow."
>In the middle of the meadow, is a bag you had brought here earlier this morning.
>You and Twilight settle down next to it as you unpack its contents.
"I was made aware that we share a common interest in astronomy." You explain in the meantime.
>"You like astronomy too? I've never met anypo-, er, anyone else who was outside of Canterlot!"
>Nodding, you continue your explanation.
"When I was a small child, my father and I would often sit on our roof and gaze at the stars. I always was interested in what could be out there."
"It's always humbling when you look up at the stars and think about how small your problems are compared to the universe."
>"I can relate."
>"Most ponies think that Luna created the night sky, but she only controls the moon."
>"Celestia told me that the heavenly objects are far older than either her or her sister."
>"Ever since I learned that, the night sky has always felt mysterious and wonderful."
>At this point, you had finished setting up the telescope and blanket. After a quick adjustment to the focus, it was ready to use.
>Your discussion quickly became about the differences in the night sky from back home.
>It was actually more similar than you expected.
>You were having fun listening to Twilight explain the names of constellations and planets, and she was having fun teaching.
>But after a few hours, Twilight gradually went from obviously drowsy, to dozing off, to actually falling asleep in your lap.
>Unwilling to wake her, you carefully pack up your things back into the bag, and then carry her over your shoulder.
>She was actually lighter than you expected.
>Before long you had brought her back back home.
>Spike let you in, and helped you put her to bed.
>As you lay her down, you wisper in her ear.
"Good night, Twilight. Love you."
>"Good night Anon. Love you too." She mumbled back.
>And so ended Anon's first Hearts and Hooves date.