• Published 22nd Aug 2017
  • 807 Views, 15 Comments

The "L" Word - Dandereshy



Hearts and Hooves Day is filled with romance, attraction, and other lovey dovey stuff that Fluttershy has never participated in - until now.

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Hearts and Hooves

Author's Note:

Heyo! Please let me know if you see any typos or mistakes. Enjoy!

Hearts and Hooves Eve. A day where ponies prepare to enjoy romance, attraction, commitment, and being in love. It's a very happy day, for those who are privileged enough to celebrate it with their Special Somepony.

But then there are those who do not get to experience such wonderful, fulfilling feelings. Not all of them are necessarily saddened by this fact, but there are a few who are. They long to be asked out, to be kissed, to be held, and to be wanted. But alas, fate just won't allow it. And one of these ponies is the sweet, gentle mare Pegasus named Fluttershy.

On this Hearts and Hooves Eve, she was spending it just as she usually did, and not unlike every other day of the year. To her, sometimes it just wasn't worth worrying about, as she could never participate anyways. But carnal desire always won her over in the end, and she wound up wishing somepony would come to her, take her hoof, and make her Hearts and Hooves Day evening magical.

It was late afternoon, and Fluttershy had just finished up her daily tasks, which included tending to the needy critters of the local forest, giving her cottage a spotless cleaning, and running a couple errands around the quiet, peaceful town of Ponyville.

But as she drew near the end of her day, thoughts of the morrow came flooding into her mind like a broken dam.

She trotted down the dirt path through town, dwelling on and entertaining her wildest of fantasies. Maybe somepony would finally ask her out tomorrow. Maybe she would work up the strength and courage to ask somepony out herself. But whom? Most stallions were taken by today. Not to mention the mare to stallion ratio was highly unfair. What would she do?

The setting sun cast an orange hue over town. It was cool, sunny, and windless. A beautiful day. Tomorrow would likely be the same, except Fluttershy would probably be spending the day indoors, away from all the... romance.

She shivered at the word. When would she be able to experience this wonderful feeling she knew so little, yet so much about? During her reverie, she walked past a couple, and overheard them discussing plans for Hearts and Hooves Day.

"Oh, dear, we're going to have so much fun! I simply cannot wait for my surprise!" the mare exclaimed joyously, cuddling up to the stallion, who embraced her tightly.

"I just know you'll love it. It's gonna be a gift you'll never forget," he said softly into her ear.

Fluttershy shivered, and realized she'd stopped in the middle of the path while eavesdropping on the couple. She shook her head and took off down the path in a hurried gait, not wanting to hear any more of what she couldn't have. But even as she hummed and sang to herself, trying to get the thoughts from her head, they forced their way back, taking control of her and making her skid to a halt, clutching her head and tearing up. Enough was enough. She needed help, and she knew just who could offer it.

Fluttershy took a deep breath and changed her direction, her new destination being the elegantly decorated rotunda called the Carousel Boutique.


Rarity was home, busy, but willing to help a friend in need. She'd set aside her gown-making to tend to her friend. The two of them sitting in the couch downstairs, Rarity asked Fluttershy to explain her problem. Fluttershy took a deep breath and began.

"Well... it's not really a problem, but... I'd really like help with, um... well, I don't know about... I... oh, shoot, I thought I had this..."

Rarity gave an understanding smile and placed a foreleg around Fluttershy's shoulders. "Dear, just relax. Don't overthink it or you'll get all stressed out. Simply relax... focus... and tell me what's on your mind. Okay? Give it a try."

Fluttershy nodded slightly and, again, took a deep breath, letting it go quickly. "Alright... I need help with... Hearts and Hooves Day..."

"Mmmmm what do you mean, Dear?"

Fluttershy sighed, knowing that most of her personal matters were now going to be known to somepony besides herself. She slouched a little, and closed her eyes as she replied. "I don't know how to romance..."

Rarity hesitated as she searched for an appropriate response. "How to romance... I'm assuming this means you've never been on a date?"

Fluttershy gave a silent nod.

"Hmmm. One does not simply know how to romance, Sweetie. It's learned with experience," Rarity said simply.

"And let me guess, that experience is through dating...?"

Rarity gave her a reassuring pat on her forearm. "You mustn't feel so bad about that, Hon. Why, I've never truly been on a date myself. Dating is difficult for most new ponies. Your first date is bound to be awkward, quiet, and unfulfilling."

"Well, that's not how Rainbow Dash said her first date went..." Fluttershy interjected, looking away, as if she was about to be reprimanded for disagreeing.

"Really? I hadn't known that Dashie had been on a date. Who is this stallion she saw?" Rarity prodded, being a bit nosy.

"She's still seeing him, and it's Soarin'..."

Rarity gave a deep hmph and scratched her chin. "Well, obviously there are exceptions. Not every date is the same, because not every pony is the same. Does that make any sense?"

"Yeah..."

Rarity realized she needed to get to the point, chuckled a little, and hugged the slightly depressed mare sitting beside her. "Don't you try too hard. That's the first thing. No stallion likes an over-needy mare. I usually play hard to get, and it works fine for me."

Fluttershy cocked an eyebrow, glancing over at the white Unicorn. "Wait... I thought you said you've never been on a date?"

Rarity chuckled again. "Did I say that? I did, didn't I? Hmm. I meant I've never been on a formal date. Yes. Maybe a few one-time swings, but never anything truly romantic. Although, it doesn't mean I know nothing of said romance." She grinned and batted her perfect eyelashes.

Fluttershy sighed again and pouted. "Tomorrow will be the same for me, yet again..."

Rarity frowned and hugged her once more. "You mustn't think like that. I know it must be hard to be alone for so long, and to see other ponies having the grandest of times, as I will tomorrow. I've got me a date with this handsome young stallion from Canterlot. He's such a darling, and so fancy! Ooh, I just know tomorrow will be-" The look on Fluttershy's face stopped her in mid-sentence. "Oh, right. Anyways, Darling, don't be afraid to ask a stallion if he has any plans. It's much less embarrassing, easier, and not nearly as anxiety-inducing to simply ask a stallion if he'll be busy tomorrow. If he says no, than you can move to the harder question."

"Which is... asking him... to..."

"Go on a date with you. Yes."

Fluttershy gave a high-pitched eep, startling the fancy Unicorn.

"I can see that this is clearly a much touchier subject for you than other ponies. Hmm. Perhaps it'd be easier for you to let a stallion ask you, instead." Rarity stood up and got on a coat. Fluttershy watched curiously and responded.

"Well, it would be... but... nopony ever asks me... Also, um, why are you putting on your coat...?

Rarity smiled gently at her friend. "We're going to go get you a date, my Dear."

Fluttershy gulped.


Rarity's plan to hook Fluttershy up with a mate for Hearts and Hooves went unsuccessful, to say the least. The mare simply could not overcome her timidity enough to actually ask any of the various stallions Rarity had introduced her to on a date. And cooperation on the stallions' part just didn't occur.

As evening approached, the two mares retreated back to the Carousel Boutique for a short while before Fluttershy would have to head home for the night.

Fluttershy sat on the big, red couch Rarity frequently used in her dramatic antics while the fashionista prepared another gown for the romantic day ahead, trying to console her friend.

"I guess I'll get back to my cottage and make some supper before I head to bed..." Fluttershy said dejectedly, staring down at the floor with an adorable pout. She stood up and stretched.

Rarity sighed with defeat. There wasn't anything she could do to fix the situation. She just had to hope for the best, that somepony would finally ask the poor mare on a date for once. "I hope your day is better than you anticipate it to be, Dear. Very sorry about today. I did all I could. For the record, you're a very attractive mare. Somepony will want you, if they don't already."

"Thanks Rarity, but I doubt it. I don't think I'm dateable material. I-I'll just head home... Thanks for the help anyways..." Fluttershy left in a hurry, before Rarity could give a response.

"Poor girl..."