Dare To Dream

by The Drunken Sailor

Rating: teen
Tags: My Little Pony: Friendship is Magic, Romance, Princess Luna, Slice of Life, Sex, Twilight Sparkle
Length: 2554

Luna and Twilight go out on their first date. Both anxious about spending time with each other and worried about the idea of a relationship.

Luna has dated before, but it has always ended badly. So when she asks Twilight out of their first date she can't help but fret and worry. About her own feelings, about Twilight's feelings, and about whether or not she deserves a relationship at all.

(Sex tag for suggestive themes)
(Cover art by: Magnaluna)

Published 2019-08-22 01:30:01 UTC
Last updated 2019-08-22 01:30:01 UTC

The Date

Dare to Dream

Luna had done this a hundred times but it never got easier.

Perhaps it was lack of practice? After all, it had been a thousand years. Though Luna had thoroughly studied every book she could find on the subject of modern-day courtship she could not escape the overbearing feeling of her ignorance. All the boxes were ticked, the list reviewed. She had applied light make up, enough to highlight her eyes and lips but not so much to appear as a clown. She had even bought flowers, roses were the choice of this era.

The regalia was gone, giving her a much more casual look. Though there was only so casual Luna could look, her, one of the Two Princesses, Goddess of the Moon and Stars, a being prayed to every night; indeed there was only so much she could strip that aura away. Luna wondered if she appeared intimidating.

"You're fretting," Celestia said from behind her. She was looking over some official documents while enjoying a cup of tea. She looked perfect without trying, Luna noted with a touch of jealously.

"I always fret," Luna said. "I need to fret if I don't fret I fail in the mission."

"This isn't a mission," Celestia laughed. "It's a date."

Date, they used to call it courting, not it was dates and dating. Yet the word still made Luna's heart skip, her legs tense and her wings ruffle. Date, she was going on a date, specifically on a date with the most gorgeous mare she had seen in a very long time. Twilight Sparkle.

It had been a great journey to get to this point, first they had become friends, then frequent pen pals, that's when the flirting began. So casual was it at first, and how frightened had Luna been when she had as casually as she could, suggested dinner. There was no romantic intention explicitly stated, but the implication was there and very strong.

"I just want it to go well," Luna said.

"It will," Celestia said assuredly.

"How can you be so sure?"

"Because you are a very pretty mare with a good personality and at least half-decent social skills," Celestia said. "And I do have to say that being Princess doesn't hurt your chances."

"Doesn't it?" Luna said. "It has before, both of us have dared to dream of romance and even... Family before, where has that led?"

"You know I don't engage in pessimism," Celestia said. "Look, we have both made mistakes before, but we're smarter for it, if I knew this would end in tragedy then would I be so strongly condoning it?"

"...no," Luna said.

"Exactly, I have seen Twilight grow into an intelligent and competent mare and now a Princess," Celestia said. "You both share many qualities that compliment each other, in fact I would bet good taxpayer money that she is fretting every bit as you are now."

"You think so?"

"I know so."

"But I know so little of how these things are done nowadays," Luna said. "What if I offer insult? Or just deliver awkward conversation? What if I assume too much and she really doesn't have feelings for me outside of being friends-"

"Luna," Celestia said firmly, looking at her now. "You're fretting, I have seen you face down whole armies and demons from the darkest depths of the abyss without fretting, now, who are you?"

"I am... Luna?"

"That's right, now go have fun," Celestia said, pointing to the door. "Or I will throw this country into economic anarchy just to make you go."

"Okay, okay, thank you, Tia," Luna said, smiling.

"Have fun, Lulu, don't do anything I wouldn't do."

"There's not a lot you wouldn't do!" Luna giggled back and left before she heard Celestia's retort.

The evening was comforting cool one with only the barest hint of Celestia's sun making the sky glow yet one could just see Luna's stars beyond that light. Luna enjoyed the gentle breeze as she glided down from the high toward of the Palace of the Two to the destination for the night.

Initially, Luna had wanted to go to one of Canterlot's most elite and prestigious restaurants, as a special treat and experience. Celestia had gently suggested that maybe flaunting royal money and showcasing wealth may have sent the wrong message. So together they had decided upon a still high quality but more humble locale, a charming traditionalist restaurant named The Copper Bit.

Luna had "pulled some strings" with the owner and had secured them a private seat sequestered just out of sight. Not that the other guests were unwelcome but Luna preferred not to be stared at the entire evening, tonight was about her and Twilight.

Speaking of Twilight, there she was now.

Standing by the side entrance that they had agreed to meet at, Luna swore Twilight glowed in the light of the... twilight. Whoever had helped her either her makeup, Luna suspected Rarity, they had done so well. Twilight's eyes were lined with a dark purple shade which made them pop intensely and draw one into them, this colour was mirrored with the dress she was wearing. Luna may have been mistaken, but the dress seemed to hug her just a tad tighter than what may have been considered respectable yet Luna found no complaint.

"I see you found your way," Luna said, hoping her smile was natural.

"I did, have you ever been here before?" Twilight asked, at least her smile seemed genuine, and her eyes... Luna had to resist staring at those jewels.

"I... I have not!" Luna nearly choked. "Shall we?"

They were welcomed by the owner, a charming older mare called Copper Spoon with a kindly wrinkled smile. She welcomed them warmly and showed them to their table, a simple affair with a red table cloth and warm orange lantern, menus already at the ready. Copper Spoon left them to decide with a wink, dashing behind the red curtain which maintained their privacy.

Luna scanned the menu, a delectable selection of homely soul food. All recipes no doubt passed down through generations of the same family. All very filling and calorie intensive.

"So," Luna said, clearing her throat. "You have been here?"

"Once," Twilight said. "After the first invasion of Canterlot, they have very good shawarma here and we thought it was the perfect way to unwind."

"Indeed, I have never heard of this shawarma but perhaps I shall try it!" Luna said. "Though I don't have the taste of battle to go with it."

Twilights laugh made Luna's face feel warm.

"I..." Luna almost gave in to her cowardice but she was committed. "I really like your dress."

"Thank you," Twilight said, oh her smile was so beautiful. "Though it took some convincing from Rarity."

"You should listen to her more often, the result is stunning," Luna said and the blush that she got in response came very close to being the thing that claimed her life. She almost missed what Twilight said next.

"What sort of wine do you prefer?" Twilight asked. "I'm not very experienced in the subject, though I read a very good book recently on the subject, Of Grapes and Fermentation."

"By Grape Juice, yes, I'm familiar, he cultivated the sweetest wines to ever grace the planet," Luna laughed. "And the parties he threw were always ones to remember!"

"I always forget you were present for the lives of so many legends," Twilight said, she sounded envious. "But you knew the master, maybe he passed on some good judgment when it comes to wine selecting?"

"Well, I have always been partial to the Colovian Red..."

Copper Spoon would soon return and take their drink order and swiftly after two glasses of a rich red wine would be placed for each of them.

"It's sweet!" Twilight said in surprise after she took a sip.

"Yes, I thought you might like it," Luna said. "There are stronger-tasting ones but I've always had a soft spot for this."

"I can see why," Twilight said, sipping some more.

"Tia has been talking about purchasing a vineyard," Luna said. "Not really for profit, but a Royal Reserve Wine brand might be interesting..."

Luna trailed off because Twilight was giggling, a girlish and adorable sound.

"What's so funny?" Luna asked, laughing along with the infectious sound.

"Tia," Twilight said breathlessly. "You don't really call her that!"

"I do!" Luna laughing. "Only in private though, but imagine the faces of the noble council if they heard that sort of talk!"

"And what does she call you?" Twilight pressed, leaning forward with a smile.

"Uh..." Luna hesitated, blushing hard. "Well that's uh..."

"Go on," Twilight, back laughs.

"Lulu..." Luna muttered under her breath.

"What?" Twilight said, leaning more forward and her smile growing bigger.

"Lulu!" Luna said, her face on fire.

"That-" Twilight giggled. "Is adorable."

"Do promise you won't spread that around," Luna said, embarrassed.

"I won't, but it's really not as silly as you think it is," Twilight said, leaning back.

They would soon place their orders, two orders of shawarma and the menus were taken away. This gave Luna concern, without the food or drink to discuss what was she supposed to talk about? She had made an extensive list the night before of conversation topics and had spent hours memorizing them, yet she could not recall a single one! All Luna could think of how lovely Twilight looked tonight...

"Have you..." Luna's throat felt dry. "Been seeing anyone recently?"

Why, why did she ask that? It was so implicit, up until now the romantic implication had been very comfortably not in the forefront. Yet Luna had brought it out into the light. Why couldn't she remember her list?

"Oh not for a while," Twilight said, the question didn't seem to faze her. "I wasn't really the dating type when I was young and I've been so busy since I moved to Ponyville, after I became a princess I got more than my fair share of stallions and mares knocking on my door but they all seemed to be more focused on the crown on my head, what about you?"

"I uh..." Luna really wished they could have kept focusing on the wine or something. "It has been a while for me aswell... I was actually nervous before coming here tonight."

Oh there it was, a full admission, this was a date. Confirmation of that fact somehow added tension to it. Yet Twilight's laugh cut through Luna's anxiety.

"You were nervous," Twilight giggled. "I nearly drove myself crazy! Lists upon lists, it's how I deal with stuff like this, Rarity and Spike eventually got me to calm down."

"Why would you feel nervous around me?" Luna asked, she was nervous because of her feelings for Twilight, but if she was nervous too...

"Well, I..." It was Twilight's turn to blush. "I uh, I've always... Thought you were very beautiful and intelligent..."

"R-really?" Luna asked, abashed. "That is what I think of you!"

Twilight's whole face was consumed by her blush, yet Luna only felt emboldened. She leaned forward and placed her hoof upon Twilights.

"I think we can feel comfortable with each other," Luna said. "We both fretted much too hard for this, thinking the other didn't... Feel the same, but knowing now..."

Luna stopped, because her warmth and confidence was replaced dread. Her past anxiety returned, not that Twilight didn't feel the same as her, but of the many mistakes she had made. Luna pulled away.

"What's wrong?" Twilight asked, concerned.

"It's just that..." Luna trailed off. "In my long life, I have sought... Connection with others many times, and every time I just end up hurt or hurting the one I care about... Me having any sort of relationship... I have always thought of it as a lofty dream."

"It isn't!" Twilight insisted. "You could never hurt me, and I would never hurt you!"

"You don't know what I'm capable of..." Luna said, looking away in bitterness yet Twilight gently turned her face to match her eyes.

"I know you," Twilight said gently. "This... This can be something, it may take a little effort, but I... I want to have it... I want... To spend time with you."

"I am... Glad to hear that, thrilled in fact," Luna said, placing her hoof over Twilight's which still rested on her cheek. "You are... A lovely mare, smart, brave, I.. Admire you and have... Felt for you for some time, and it brings me joy to hear that you feel the same."

Twilight smiled, no words needed to be said. Their food arrived and both of them eat happily, the anxiety had vanished. They chatted comfortably about the good food, about books they were enjoying, Luna promised to show Twilight her art pieces and Twilight was excited to discuss her own writing with Luna. The night concluded happily and they left Copper Spoon a big tip.

"I'm glad you asked me out," Twilight said as they walked out the way they came. "I don't think I would have ever worked up the courage to do the same, I had written up seven drafts of a letter but kept re-writing it."

"Tia was the one that got me to do it," Luna admitted with a laugh. "Practically held me down and wrote the letter herself."

"So..." Twilight said, looking up at Luna. "This was... Fun."

"When can I see you again?" Luna asked.

"I'm free Tuesday," Twilight said immediately and eagerly. "How about Ponyville this time, meet me at my place?"

"I shall..." Luna said, and then came the moment. Just before they were to part, Twilight looked up at Luna eagerly and with expectation. Her eyes reflected the moonlight. Did Luna dare? Well, she had been quite daring all night, what's a little more?

Luna lowered her head and softly placed a kiss upon Twilight's lips, it lasted only a second. It was quick but passionate, and it promised more; much more, in the future.

"Goodnight, Twilight," Luna said softly, her face still close to Twilight's.

"Goodnight... Lulu," Twilight said, her smile was full of humour and affection.

Oh, how the night air felt as Luna flew back to the palace. She felt weightless, her heart was still beating hard but from excitement and not anxiety. She actually had to stop on a nearby roof just to let out a little dance and excited squeal, like a schoolfilly she felt! Rolling in the air and somersaulting right into the room she had left from.

Celestia was still there, seemingly unmoved as she looked up casually when Luna came through the window.

"So..." She said, her expectant smile betrayed her. "How did it go?"

"Fantastic," Luna said breathlessly. "Oh, she is just lovely Tia, her face, her eyes, her voice! We promised to meet again and I'll be counting the seconds!"

"Seems like you were wrong to fret then," Celestia said.

"You were right Tia, you really were, thank you," Luna said happily. "This... This could go somewhere... I want it to go somewhere, maybe this could be it, is that silly? I cannot tell."

"Dare to dream, my sister," Celestia chuckled. "Dare to dream."

Author's Note

Some fluff.