He Loves Me, He Loves Me Not

by Flagstar of Flagclan

Rating: everyone
Tags: Other, Romance, Princess Luna, Original Character, Princess Celestia, My Little Pony: Friendship is Magic, Sad
Length: 3440

Luna falls in love with one of her dark royal guards, but can't seem to get a date with him. Celestia tries to help by being her wing pony but ends up just getting annoyed by his annoying friend. Now Luna doubts and Celestia gets annoyed.

Luna tries to find the guts to ask out Shackles, one of her royal guards and the love of her life, but can't seem to. Celestia helps by being her wing pony and going out with his annoying friend, Thorn. When Luna asks him out he says no, leaving her heart broken. As her older sister lends a hoof to help get her confidence back up, Thorn annoys the crap out of her, making it even harder for her to help Luna. Will Luna ever get her date? And will Thorn get to go out with Celestia?

Published 2014-08-12 20:40:05 UTC
Last updated 2014-08-18 21:43:56 UTC

Wing Pony?

Luna sighed as she sipped her third glass of punch. She looked over across the ballroom to see him sitting all alone. He looked very vigilant, glancing at her every so often. Luna felt confused, wondering if he was just doing her job or if he possibly liked her. She wanted to ask him out, but couldn't find the courage. She was a princess, and even though she's been trapped in the moon for a thousand years, she still knew how to date. Ever since she hired the new guard pony she couldn't think straight. All she thought about was how his face was perfect and he had the best looking wings, with totally wicked fangs to pull off the character. Celestia was standing next her, shaking her head.

"Sister, you need to talk to him."

"I can't. What if he doesn't except me?"

"Shackles clearly likes you Luna. You just need the guts to go and ask him for a dance."

Luna shook her head. As much as she wanted to, she was afraid he may reject her. She closed her eyes and thought about the day he had first come into Canterlot, looking for a job as a dark royal guard.

Luna was sitting in the throne room with her sister, talking about the plans for the new city.

"It should have something that screams wonderful." Luna said.

"I know. So what shall we put in there?"

Celestia and Luna both closed their eyes to think. The same idea seemed to come to them as they both said the same thing.

"A dance club!" The sisters said in unison.

One of the royal guards opened the door. Next to him was a dark violet pegasus. Luna put a wing over her face to hide her blush. Both ponies bowed their heads.

"We are sorry to disturb you, your highness's, but this pegasus wishes to become one of the guards for Princess Luna."

Celestia looked at her younger sister and gave a small chuckle when she saw her blushing. Luna did her best to put on her serious look and took down her wing. She looked at the violet pony.

"I suppose since one has quit it would be beneficial to have another guard as soon as possible." She said with a high note of authority. "So due to this problem I accept your offer of being my royal guard."

The pegasus gave a wide smile and bowed.

"Thank you Princess Luna."

Celestia looked at both of them. "Ahem! What is your name?"

"Shackles."

She nodded and dismissed them. The two ponies left the room and she turned to Luna.

"Somepony's got a crush."

"I do not!" Luna said, trying not to blush again.

"Then why are you blushing?" Celestia said, a large smile on her face.

"I'm not blushing!

Luna giggled at the memory. Even though she was really nervous the memory made her feel better. Celestia smiled, clearly knowing what she was thinking. Luna turned back to look at Shackles and sighed.

"Sister, I have an idea."

Luna groaned. "What?"

"How about you ask him out and I'll be your wing pony. I can go out with Thorn. Besides he's always asking me out anyways, so it would be easy to make it a double date."

For once she felt like her sister's plan may work. It seemed logical, and she knew Thorn had feelings for Celestia. Luna nodded and set down her punch glass. The two sisters headed over to Shackles, who was now talking to Thorn. She took a deep breath and smiled.

"Hello, Shackles."

"Hi, Princess Luna." He said with a bow. "What can I do for you?"

"I was wondering if you would like to....." She took another deep breath. "go out with me?"

There was a look of happiness that spread across his face but quickly disappeared.

"I'm sorry, but I can't."

Luna just nodded and headed back towards the punch table. She grabbed her punch again and started to sip, trying to hold back tears. Celestia came up beside her and put her wing around her.

"It's okay Luna, I'm sure he was just nervous."

Luna looked at her older sister and gave her a death stare. She flinched but held her ground, only removing her wing.

"This is all your fault! If only I had ignored your idea!" She yelled, running out the door.

Celestia sighed and started to slowly follow her. She knew it was just the pain talking but it felt as if Luna had ripped her heart out.

"I was wondering if.....you would go out with me?" Luna said.

Shackles nearly fainted, a smile coming across his face. He quickly hid it, thinking it could just be a joke. He hoped that it would be real but was scared that Luna was just pulling a prank on him, as she sometimes did with her guards. She wasn't usually this deep into it, it was pretty much just snake cans and squirting flowers with her, you know the light stuff, but he didn't want to take any chances.

"I'm sorry, but I can't" Shackles replied, forcing out every word.

Luna walked away with a nod and he felt a pang of sadness. "Maybe she was sincere." He thought. Suddenly, he wanted to run up to her and change his answer, but he stayed where he was. Thorn gave him a stern look.

"Dude! Princess Celestia was with her! Maybe she wanted to double date or something! Now you ruined my chance!" He said angrily.

"I just thought she was playing a prank on me! How was I supposed to know that she was serious?"

"Oh I don't know, look at her expression! It cried I love you all over it!"

Shackles shook his head. He watched as Luna ran out of the ballroom, Celestia trailing behind her. He thought maybe he could go and apologize, so then they could go out, but thought better of it when he saw a look of rage on her face. He grabbed his spear that was hidden behind a curtain and walked out after them. Thorn slowly followed behind.

"I have an idea," He said.

"What?"

"How about I ask Celestia out on a date. We could do a double date so you could be with Luna." Thorn said tentatively.

Shackles smiled. "That's a perfect idea."

The two colts headed for the castle, talking about their plan all the way there.

Author's Note

This is my first chapter. I know I haven't finished any of my books yet but I'm close with one, and the other will never end until a couple of years. Okay maybe a bit less than that but still. I hope you enjoy this love story! :)

I just got done with some major corrections on it. Thanks for everyone who has helped.

Love is so confusing!

Luna locked her door and hopped on her bed. She let out a loud high pitched scream and started to cry. All her hopes and dreams, crushed by this one moment. She thought that the pain of rejection wouldn't be this bad, but was totally wrong. When Shackles told her no at the ball, she had felt her heart rip into a million pieces. Her sister had told her that she would be her wing pony and help her get a date. "That's the last time I trust her ideas!" She thought to herself.

She knew it was wrong to blame her, but she couldn't help it. Luna was perfectly comfortable sitting there and drinking punch. Even though she really wanted to go and ask him out she was afraid. She shook her head to clear it. She wished she could take back that moment but knew it was impossible. A knock came from her door, causing her to break out of her bad memories. She wiped away her tears with her hoof and gave permission to enter. Celestia came through the door.

"I'm so sorry Luna," She said.

"It's fine, I just can't believe he said no."

Celestia walked over and gave her a big hug. Luna hesitated but returned the affection, already feeling better. After a few moments they stopped and looked at each other.

"I must go now," Celestia started, "I have to go and write a letter to Twilight."

She headed out the door, leaving Luna alone. The alicorn used her magic to lift up her favorite novel: New Moon. It was part of the Twilight series. She had been reading it for several days after she finished the first book, hoping it would give her an idea on how to ask out Shackles but it was no use. These ponies were so weird with their vampires and werewolf issues. She opened it up and started reading. She had only read a couple of pages when she got bored.

Luna turned on the TV to see a new episode of Random Events on. She smiled when Derpy cheered over winning muffins.

"Maybe I should do that show," She said out loud.

Another knock came one her door. She sighed.

"Come in!"

Shackles came through the door. Luna wanted to hide but held her ground. He had a sheepish smile on his face, clearly feeling uncomfortable.

"I wanted to um.....apologize." He said

She gulped, "Why would you need to apologize?"

"When you asked me out, I thought you were playing a prank on me, so I said no. When I realized that you were serious, I wanted to change my answer."

"Oh."

"So is that offer on the date still open? I would understand if you said no....."

"That would be splendid!" She said with a smile.

Shackles smiled back. "That's great. So how about I pick you up at eight and we'll double date with Celestia and Thorn?"

She nodded. He left the room with a skip and a jump. Luna waited for him to leave the room, then gave a giant jump.

"Woo hoo!" She yelled happily.

Celestia walked out of the room and headed towards her own. When she got there she took out a quill, ink, and a piece of paper. She started writing a letter but got distracted with Luna's feelings. It felt like she had failed her sister. 'Maybe forcing her to ask him out was a bad idea.' Celestia heard someone clear their throat outside so she opened the door. Thorn entered the room, a small smile on his face. He bowed his head.

"Hello, Princess Celestia."

"Hello, Thorn. What brings you here?"

"I was wondering if you would like to double date with me and Shackles?"

Celestia took a deep breath. "Is Shackles asking out Luna?"

"Yeeeaaahh....."

'Curse me promising to be the wing pony!' She thought to herself.

"Of course I will go out with you."

Thorn gave her a wide smile. She couldn't help but smile back, glad that she made somepony happy tonight.

"Okay, I'll pick you up at eight, cupcake!" He said excitedly.

She nodded and he headed out the door. Celestia waited for a few minutes then exited the room. She found her hooves taking her towards Luna's bedroom. She saw Shackles leaving, then heard a loud cheer from her sister. Celestia knocked on the door and heard an excited 'enter'.

"Ooo, guess what! Shackles asked me out!" Luna said as she entered.

"I know, so did Thorn. I guess we're double dating."

Luna looked like she was gonna explode with happiness. Celestia was glad that her sister was in a good mood after her horrible night.

"I can't wait! Oh my gosh, it's gonna be eight in an hour. You better leave so I can get ready!"

"Okay, see you in an hour."

Celestia exited the room and headed back to hers. She opened her closet and started looking through her things. There were so many dresses to choose from that it made her head hurt. Finally, she decided on a rainbow dress with glass slippers. She chose a black hat covered in sequins to go with it.

"Maybe this won't be so bad." She whispered under her breath.

She wasn't so keen on going out with Thorn. He was really nice and had looks but he was just too perky. Maybe they could make it work but Celestia was afraid he may get on her nerves too often. She silently worked on combing her hair for tonight's date.

Shackles waited outside of Luna's door. It was almost eight and he was so excited.

"Are you almost ready Luna?" He called.

"Yes, just give me a minute."

After a few moments she opened the door. His jaw dropped wide at her beauty. Luna was wearing a dress that seemed to be made of stars. It had matching shoes to go with it. Her crown was black with a red jewel on the top. Shackles shook his head so he could clear it. He didn't wanna do anything to ruin this date and he couldn't think straight with her beauty coming at him in waves. She smiled at him, causing him blush.

"This is gonna be a really good date." He thought to himself.

He took her hoof in his and led her towards the other couple.

Author's Note

I really hope this is a better chapter. My first one wasn't the best so I hope this will turn some of the dislikes into likes.

Corrections made on this chapter too. Thanks so much for all these corrections, I'm just noticing all of these mistakes now. (Wow I'm pretty bad at this.)

A Great date? As If!

They two couples headed towards the Pizzeria. It wasn't the most romantic place Shackles could think of but there weren't many restaurants in Canterlot, well for what he knew of at least. Luna smiled at him. He looked over to see Celestia and Thorn walking together, though Celestia kept her distance.

"So what's you favorite color?" Thorn asked her date.

"Pink. yours?"

He smiled, "Red."

Shackles noticed she didn't return the smile. They came up to the restaurant and he opened the door for Luna. She smiled and entered, Celestia following her. He requested a table for four. The waiter, a red unicorn, led them to a booth in the back of the restaurant. She asked for drinks and all of them ordered a lemon iced tea.

"Shackles?"

He turned to Luna, "Yes?"

"I'm really glad you brought me here."

"I'm just glad you let me bring you here after I, uh, you know."

Luna frowned a little, "Yeah, I know."

He shifted uncomfortably and tried to listen to what Thorn and Celestia were talking about.

"So have you ever heard of slorgs?" Thorn asked his date.

"No, what are they?"

"Green slimy creatures."

Shackles sighed and tried to return to his conversation with Luna. She was still looking at him, her small frown gone. He was about to ask her about the weather when the red unicorn came back with their drinks. After they all got menus he tried to talk to her again.

"So how about this weather lately? The pegasi have really outdone themselves, keeping all the clouds away. Not to mention," he started saying with romantically, "this beautiful night of yours."

Luna blushed, "It's just the usual."

"Oh, that's such an understatement. When you came back the nights were so much brighter."

Celestia gave a small growl. Shackles did his best to ignore it, wanting to focus on his date.

Celestia gave a small growl. "How dare he say her nights are better than mine!" She thought bitterly. She sighed, feeling ashamed, knowing that she had no right to be mad. "He's just trying to get her to like him more." Celestia told herself. She turned back to Thorn, who was concentrating on his menu. She knew she might as well start a conversation.

"So," She began, a little out of practice, "Do you have any siblings?"

He looked up from his menu and smiled.

"No. Do you have any siblings, you know, besides Luna?"

"Sadly not, though I do have an adopted niece, Princess Cadance."

The red unicorn came to the table and took their orders. Celestia was going to order a mini pizza when Thorn got a couples pizza. She sighed in defeat. "Clearly nothing will go my way tonight," She thought sadly. Thorn got up and whispered something to both Shackles and Luna. Both of them smiled. Luna switched places with him so he could sit right next to her.

"Just my luck," Celestia said under her breath, "I have to sit right next to him now."

"What was that dear?"

She tried to hide her embarrassment of being heard, "I was just saying how happy I am that you're sitting next to me."

He gave her a quick kiss on the cheek. Suddenly, she felt something she hadn't felt in a while. The feeling hadn't been there since she broke up with her first ever boyfriend, Lightning Rider, a pegasus who had stolen her heart, but never truly cared about her. She had never trusted another boy since, afraid for the same type of rejection. Celestia had only agreed to this date for her sister, but was surprised to find that she had feelings for this pony.

"The pizza's here," Thorn said, waving his hoof in her face.

She blinked away the memories and stared at the food. She hadn't realized how hungry she was. The unicorn set down the food and left, not bothering to ask if they needed anything else. Celestia felt a small pang of excitement at the thought of sharing something with her date, but quickly ignored it. "I don't need to feel such feelings for somepony who may not care for me back. For all I know he could be acting." She thought to herself.

Thorn took a knife and split the pizza in half. He smiled and took a bite out of his half. Celestia felt him scoot over, making it so there's no room between them. "Maybe he does like me," she thought. The waitress came back and asked how they were doing. When Celestia told her that she was finished, even though she barely ate, the unicorn used her magic to get the plate. Luna gave a large stretch, accidentally spilling her drink on the waitress. The red unicorn stopped using her magic due to shock and ended up dropping the plate on Shackles's head. He turned red and gave the unicorn a death glare.

"What was that for, stupid? Can't you see I'm on a date here? I mean, are you trying to ruin it?" He screamed at her.

"I, I'm s, s, sorry! It was a, an accident!" The mare replied in a scared voice.

"Yeah right! And pigs fly you stupid, pathetic piece of.....," he began, only to be cut off by Luna.

"There is no call for that kind of language. And the only one ruining this date is you, for being such a hot head." She turned to her sister, "Come, Celestia! I believe we have business elsewhere!"

The two mares left, leaving both colts angry. When they were outside Celestia looked at Luna.

"Are you okay?"

"No! This feels like the ball all over again, except this time the feelings are stronger!"

"I know it hurts to have your heart broken twice in the same night, but I'm sure it will get better." Celestia said, trying to calm her sister down.

"Ya right!"

And with that Luna turned and ran down the street. Celestia thought about following her, in hopes of calming her down, but decided she needed to cool down on her own. She spread her wings and flew off towards the castle, feeling a pang of sadness.

"Maybe I should try to calm the colts down?" She asked herself. Celestia shook her head. "I've done nothing wrong, and I don't want to get into another fight tonight."

When she got to the castle she headed towards her room and closed the door, even locking it for good measures. Then she took off her dress and slipped into her night gown. Celestia closed her eyes, hoping she could get some sleep, but the events of that night kept her awake.

Author's Note

This chapter may be a little rough, but if you see any errors that need correcting I'd be glad to hear them. I've been getting a lot of help so far and I'm really thankful. Thanks!