• Published 16th Nov 2021
  • 1,295 Views, 37 Comments

Let Yourself Fall - Briarberrybones



New feelings can be a bit hard to navigate. Perhaps some friend's advice and a beautiful dinner date in the Everfree Forest can help?

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Armed and Ready

Fluttershy had plenty to mull over after her chat with Applejack and luckily the walk to Rarity’s boutique was a decent ways away; giving her equally enough time before having to spill out a little bit more of her heart.

“Perhaps you can get a better read on what this…stallion is feeling by thinking back on how he acts around you?” Applejack’s kind words of advice were spinning around her head. “How he acts around me, huh?” She began making a mental bullet point list. She knew full well that he at least enjoyed spending time with her.

Early on in their friendship, she was concerned that the effort to see her weekly may have been for show. Perhaps to appease the princesses and make it at least look like he was reformed? However, that thought was easily erased over a rather short time when he had shown that he very much did enjoy their tea dates and he did enjoy being around her; and cared for her. It was very apparent in his frequent letters leading up to every Tuesday, his misplaced jealousy of TreeHugger, when he singled her out to rescue her from the changelings, and not to mention that one time he had made such a fuss over hosting their next get together and nearly wasted away trying to make her comfortable. Remembering his first hosting attempt brought a small blush to her cheeks.

He had gone through so much trouble just to try to make her feel at home. She remembered how sad it was to see him try to change for her approval and how genuinely concerned he seemed that ponies around town didn’t believe that they were close, or maybe even thought that they shouldn’t be. She had set him straight though, letting him know that she liked him perfectly the way he was and nopony else’s opinions of them mattered. She meant it then and she meant it now.

That warm and loving glow was beginning to grow in her heart again and as she continued her way, the small smile tugging at her lips was proving hard to fight. “Applejack had also made it seem like Big Mac enjoyed trying to touch Sugar Belle as well as just being around her,” She noted to herself.

Fluttershy furrowed her brow in concentration at the thought. Discord was most definitely a touchy pony, or draconequus, she corrected herself. He made invading pony’s personal spaces a regular habit, but more so only to get a rise out of them. He wanted very much to be accepted by ponies again, or to at least be tolerated enough that he wouldn’t be bothered, but he still enjoyed startling everypony he knew and making them just a little uneasy about his presence. The way he behaved around Fluttershy did seem to be a little different, however. Whether in front of friends or in private, he was always far gentler with her than anypony else. His voice would always soften and at least once during every Tuesday tea party he had always found a reason to touch her in some friendly way, sometimes lingering in it.

“Could he actually? Maybe? Oh, I shouldn’t get my hopes up just yet.”

Fluttershy had arrived at the storefront of Rarity's boutique a little quicker than she'd anticipated and was beginning to have second thoughts. Confessing to Applejack that she was interested in anypony was a massive leap of bravery for her, but to Rarity too in one day? It was all happening so quickly, it made her shaky at the knees, but she knew Applejack was right. Rarity was a known helpless romantic who'd had her fair share of stallion experience. Fluttershy was more than just a fish out of water to the matter, but knew deep down that learning how to flirt, even just a little bit, might come in handy.

With a gulp, she lightly knocked the door with her hoof.

A few moments of silence passed. Fluttershy was about to call it quits and turn tail, when she finally heard Rarity's voice echo from the other side. "One moment, I'll be right there!"

The door opened rather abruptly to reveal a pleasantly surprised Rarity, dressed in an extravagant purple feathered gown. "Oh, Fluttershy, darling! What are you doing here? Did I forget our spa day?"

"Oh, no." Fluttershy could feel the heat returning to her cheeks as she thought about what she'd say next. "Um, Rarity. If you're not too busy right now, could I ask you for some advice?"

Rarity's smile began to fall at the serious tone of her friend's question. "Of course, darling. Whatever is the matter?"

With one more gulp, Fluttershy spoke, barely above a whisper, "Um, could you teach me how to...flirt?"

In a flash, Rarity had grabbed Fluttershy by the hoof, yanked her inside the boutique, locked the door, and rotated the "Open" sign to "Closed".

She was practically being carried up the stairs to Rarity's personal arsenal room of fashion weaponry. In the same motion, she was sat abruptly on a very plush loveseat, with a glass of what smelled like wine suddenly appearing in her hooves. A very giddy Rarity appeared next to her, now adorning a violet bathrobe and wine glass of her own balancing in one hoof, the other perched beneath her chin. The overzealous look she was giving Fluttershy, had her just a tad nervous about what she may have just unleashed.

Rarity gave her a soft, but very impatient nudge to her shoulder. " So darling, what all would you like to know and just WHAT brought this up?"

Fluttershy was quickly beginning to resemble a ripe strawberry in the face and stuttered, "Well, um, Rarity... I... oh gosh, I'm not sure how to say this now."

Rarity relaxed a bit, she was always so quick to get excited about anything that involved romance and to hear it suddenly coming from her dear, sweet Fluttershy, it was all but impossible to contain her glee. However, she should've known that Fluttershy would be reacting this way. She was such a private pony about all her feelings. She was clearly flustered, and Rarity realized that her reaction to the matter, although genuine, probably was a bit over the top.

"I'm so sorry to make you nervous, dear." She said, placing a now reassuring hoof on her friend's shoulder. "Please tell me what's happening. I'm just a bit surprised to hear you mention anything about flirting or the need to. I'm just excited for you!"

Rarity's shift in tone had calmed Fluttershy to a point where she could at least string her thoughts together in a cohesive sentence.

"Well, um... I've recently realized that I may have feelings for a very close friend of mine."

"Mhmmm," Rarity ushered. Still a little too excitedly and... a little too knowingly.

"And well... I'm trying to figure out if he might feel similarly about me, but I'm not so sure what I'd even do if I found that he does." That last part left her lips a little quieter. Almost like she was still trying to convince herself that there was a smidgen of a chance.

"Oh, Fluttershy, dear! Again I'm so happy to hear this, but why do you seem so gloomy about it? I don't mean to assume, but I can feel an uncertainty in your voice," Rarity replied.

"Well, I'm still not so sure if I'm really the right pony for him. I just still can't shake the feeling that maybe somepony else could make him happier. That and I'm still not fully confident that my heart could handle the rejection if I'm right."

Fluttershy glanced up from her twiddling hooves to see Rarity sporting an identical expression of frustration that Applejack wore when they'd spoken earlier.

Rarity firmly sat her wine glass down on the end table with a "hmph" before shooting Fluttershy with the most offended daggers she'd ever mustered.

"Fluttershy, how dare you underestimate yourself like that!" She was leaning further towards Fluttershy with every word. "You are easily the most graceful, elegant, enchanting pony I've ever had cross my life! Why on earth do you think I had begged you to be my model so long ago! 'Perhaps somepony else could make him happier?' Pssssh," she spat. "Darling, I promise you that you are the absolute envy of every mare around! Any stallion should feel honored that you'd even bless them with a sideways glance!"

Fluttershy leaned away into the farthest arm of the loveseat. Rarity was lost in her rant, and she knew there'd be no way of stopping her until she was finished.

"Darling, you are the epitome of patience and kindness in the most literal sense! A strength that we all could use more of. My goodness, if that big buffoon even had half a head on top of that long neck, he should've wed you yesterday!" Tire wheels screeched Rarity's fiery speech to a halt.

"Wait... what was that last par-?"

"Nevermind that!" Rarity cut her off. "I'm sorry, darling, you are just such a special mare and friend to me that it makes me a bit upset to hear you degrade yourself like that, but please trust me when I tell you that all I say is true. I promise you that you should have no worries what so ever about whether this um... stallion...should find you attractive, let alone marefriend or wifey material."

Rarity was quick to notice the sudden color in Fluttershy's cheeks at the mention of marefriends and implied marriage, but it was the smile tugging at her mouth again that let her know that it was finally starting to sink in.

"Thank you, Rarity. That all means a lot. I just get so lost in my doubts sometimes, and I do feel a bit better, but... um... again let's say that this stallion feels the same way about me. How should I....", she gulped. "Court him?"

Before Fluttershy could register what'd happened, she'd been dragged to the center of the room. Rarity was circling her with a sly smirk.

"Now darling, since you ask, the first thing that should happen is that the two of you should enjoy a date together. Not a hang out, a real date! Complete with a romantic ambiance, but that's where the fun really starts."

Fluttershy swallowed her nervous "eep" at what Rarity could possibly imply next.

"Now of course when I say 'romantic', it should still be a setting that you both feel comfortable in. A place where you can both feel yourselves... of course some proper lighting can certainly help set the mood."

"Oh?"

"Oh, yes! Now the time and place are only half the work. Next, you'll need to show off your assets to entice him in!"

"Pardon, but my what?!" Fluttershy had said that I little more loudly than she'd liked.

"Oh, sweet Fluttershy!" Rarity giggled. "You're so cute. Of course, I encourage you to move at your own pace and only do what you're comfortable doing, buuuuut... you should know that males are very visual creatures. Sometimes you must communicate what you're wanting with your body!"

She was circling Fluttershy a little more frantically, looking for the perfect "material" to work with.

"You have a positively luxurious mane, darling. Give it a little flip or twirl during conversation! Your eyes are beyond mystical. Give him some eye contact but keep them relaxed and... dreamy if you will." She paused and examined Fluttershy's tail with that knowing smirk again. "And speaking of assets, don't be afraid to give this flank of yours of little swish and sway if the night's going well."

Fluttershy could do little to hold in her gasp at Rarity's last tip.

"Oh, don't fret about it too much, dear. You'll know what to do when the moments are right. And um... perhaps if the two of you are as close as you say, it may come easier than you think. Ahem." She coughed lightly into her hoof. "But um, remember again that males tend to be a bit simple when it comes to courtship, but they do love a chase."

"A chase?" Fluttershy pondered the notion; a mental lightbulb beamed to life in her head. She knew just what she'd do.

"Do you feel prepared, dear?" Rarity asked, a little too elated at Fluttershy's apparent change in demeanor.

"I think so. Thank you so much, Rarity. I was really nervous about this whole thing, but I'm feeling a bit more confident about it all and maybe even excited?"

Rarity squeezed her hard into the tightest hug. "I'm so proud of you! You'll do splendidly. Just remember to be yourself and have fun. That's the most important part!"

With that, Fluttershy left the boutique feeling radiant. She'd been given no make over or fancy new gown, but she certainly felt that glow just a little stronger than before. However, her mission wasn't complete. She had an ounce of newly found confidence and a mini arsenal of flirtatious tips, should all head in a positive direction, but there was still a very important piece of information she needed before she could throw herself all in.

"I need to talk to Spike."

Author's Note:

A bit of a long chapter, but Rarity was just too fun to write. A lot of inspiration here came from personal experience during my first year of college. My friends were going to great lengths to teach me how to flirt and prepare my silly ass for the first date with my now husband. So I guess it worked?