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Courting Shynon

By Hearthsong
Created: 2026-03-14 11:54:08
Updated: 2026-03-17 05:23:20
Expiry: Never
anontwilight sparklefluttershypinkie pieraritysafeshy family anonromance?

  1. 1.
    Remember when this was originally conceived as an Anon/Pinkie story?
  2. 2.
     
  3. 3.
     
  4. 4.
    Part One:
  5. 5.
    >Evening has once again descended upon Ponyville
  6. 6.
    >A rare quiet one at that, beyond the sounds of birds chirping away in the trees, the sounds of hooves clip-clopping as Ponies make their way home or to the various restaurants and such to while away the hours, work blissfully in the proverbial rear view mirror
  7. 7.
    >You would be joining them usually - the karaoke bar that recently opened on Whitetail Road has been calling your name, but the week's just been far too busy to make an appearance
  8. 8.
    >Unfortunately, your saddlebags have just a teensy bit too much weight for that just yet
  9. 9.
    >One more delivery to be made before it's time for fun
  10. 10.
    >Speaking of calling your name, what is it, anyway?
  11. 11.
    >Why, (You)'re the Sultan of Soirees
  12. 12.
    >The Countess of Celebrations
  13. 13.
    >The Dame of Disco
  14. 14.
    >That's right, (You) are Pinkie Pie
  15. 15.
    >With a pronk in your step and a content smile on your face, you make your way to the last destination on your delivery route
  16. 16.
    >The Carousel Boutique!
  17. 17.
    >Rarity specifically prefers her order of blueberry eclairs to be delivered late like this
  18. 18.
    >One part that generous nature of hers letting everyone else get their treats first
  19. 19.
    >Another part claiming that something sweet just perfectly hits the spot after a long day of sewing
  20. 20.
    >A sentiment you can absolutely agree with!
  21. 21.
    >You've got several cupcakes waiting to reward you for your own hard work waiting at Sugarcube Corner
  22. 22.
    >But again, first, seeing to your friend
  23. 23.
    >It wouldn't be much of a faux paus to barge right into Rarity's home slash place of business, given your relationship
  24. 24.
    >But you are here on business yourself, so you dutifully rap your hoof on the door to announce yourself
  25. 25.
    >You're just so excited to see Rarity though you can't help but shriek and toss some confetti stashed in your mane into the air when she opens the door
  26. 26.
    "ECLAIR DELIVERY!"
  27. 27.
    >To your dear friend's credit she's only momentarily stunned by the burst of noise before composing herself
  28. 28.
    >"Excellent timing, darling! I had just powered down my sewing machine and put my needles up for the night. Please, do come in."
  29. 29.
    >Rarity opens the door wider and steps aside to allow you entry, which you oblige
  30. 30.
    "Mhm! Sugarcube Delivery prides itself on our timing! That and our quality baked goods!"
  31. 31.
    >To be honest you kind of just wandered around town aimlessly throughout the past few hours
  32. 32.
    >Your patented Pinkie Sense gave you a good drumming whenever it felt it was about the right time to lighten your saddlebags load
  33. 33.
    >It all seemed to work out though, so you weren't going to complain!
  34. 34.
    >Digging your nose into your saddlebag, you balance the paper box on your snout before setting it down on Rarity's kitchen counter
  35. 35.
    "Ta-da! One batch of super yummyrific eclairs!"
  36. 36.
    >Rarity joins you in the kitchen, using her magic to open the box and take one of the treats to daintily nibble on. True to form, she offers you one as well, and it would just be rude to say no!
  37. 37.
    >The expression of delight on your friend's face is enough to get you grinning ear to ear before you take a bite yourself
  38. 38.
    >You baked them yourself, after all, and knowing they're adored is almost as filling as eating them yourself
  39. 39.
    >"Divine as always, Pinkie! You never disappoint. By the by, if you don't mind me asking, are you doing something new with your mane?"
  40. 40.
    >Unceremoniously, you toss the offered eclair into the air and catch it with your mouth, where it vanishes almost immediately
  41. 41.
    >You get a brief taste of blueberry before it's banished to the void that is your tummy
  42. 42.
    >At Rarity's question, you take a brief peek at your reflection in one of the unicorn's many conveniently placed mirrors
  43. 43.
    >Your reflection tips you a playful wink as you reach with your hooves to tease at your mane
  44. 44.
    >It is a bit different
  45. 45.
    >The big poofy curls are almost completely deflated
  46. 46.
    >Normally a cause for concern, but it still bends in wild directions at the ends
  47. 47.
    >Not full on depression-mode, though you can't fault others for assuming such
  48. 48.
    >Just... relaxed
  49. 49.
    >Calm
  50. 50.
    >It's usually a foreign feeling, something you only really engage with for a few minutes in the morning before you fully wake up and remember all the super fun and fantastic things you have planned for the day
  51. 51.
    >But the entire town's been feeling a welcome malaise for the past week
  52. 52.
    "I wouldn't say I'm doing anything specific! It's just... kind of happening."
  53. 53.
    >"Oh, just a natural phenomenon, then? Nothing to do with a certain stallion?"
  54. 54.
    >You toy with your at ease mane, coiling some of it around your hoof as you consider the cause:
  55. 55.
    >One Pegasi whose calming vibes were so strong that even an entire village wasn't safe from chilling out:
  56. 56.
    >Gale Incognito, Fluttershy's younger brother (Anon to his friends, which you're pleased as punch to count yourself as!)
  57. 57.
    >The Pegasus had come to town to visit family after several years of estrangment
  58. 58.
    >Though certain... complications regarding her coltfriend(?) had swiftly made it go from a family visit to a vacation in the Chaos Capital of Equestria
  59. 59.
    >As the Premier Party Pony of the town and a One-Pony Welcoming Committee, you were happy to introduce Gale to your beloved town
  60. 60.
    >Introducing him to the best Sugarcube had to offer
  61. 61.
    >A tour of the eclectic shops (he took to the idea of Quills and Sofas a lot quicker than the usual visitor)
  62. 62.
    >Even a walkthrough of Twilight's shiny new castle, where you only got lost eight times! A new record!
  63. 63.
    >Circumstances led to you chaperoning Gale for most of the week
  64. 64.
    >It was fascinating to see how his vibe radiated through the town
  65. 65.
    >Just a few days in and the hustle and bustle of Ponyville had calmed down entirely
  66. 66.
    >A bugbear had broken into the Town Square around Day Four and was so taken with everyone not screaming and panicking that it just... chilled out
  67. 67.
    >By the time it eventually returned to the forest, Daisy, Roseluck, and Lily had braided its' fur with several dozen of their flowers
  68. 68.
    >You wondered briefly if it let them do that because half of it was a bee and bees loved flowers
  69. 69.
    >Before you could get too lost in thought (or even moreso), you felt eyes on you and realized Rarity was staring at you with the most coy expression she could muster
  70. 70.
    >Apparently you had been reminiscing about Anon for way too long (over 1500 characters, wow!) without answering her
  71. 71.
    >And that had given her ideas
  72. 72.
    >"My my my, darling, I think that's the longest I'd heard you gone without a peep. Was I on the money about you perhaps being taken with our latest visitor?"
  73. 73.
    >An exaggerated scoff erupted from your muzzle
  74. 74.
    >"Rarity, hey, come on now. Gale's been real fun to hang out with, but... geez..."
  75. 75.
    >You really hadn't met many ponies like Gale before
  76. 76.
    >The closest comparison you could make was your beloved sister Maud
  77. 77.
    >Though Gale wasn't quite as stoic as her
  78. 78.
    >He had a quiet, unshakeable confidence
  79. 79.
    >Not concerned with being the center of attention but with a passion that made it easy to get eyes on him if he wanted
  80. 80.
    >Even boring things like listening to him and Twilight discuss cloud maintenance and identification had kept your attention just through the sheer magnetism of his passion for the subject
  81. 81.
    >Granted, you could absolutely listen to Maud talk about geology for hours for the same reason
  82. 82.
    >"Don't protest too much now, dear. He is a fine young stallion, after all. And pickings are slim in this little town, aren't they?"
  83. 83.
    >That was true...
  84. 84.
    >Most of the stallions in Ponyville were either taken, like Time Turner or Mr. Cake
  85. 85.
    >Or simply not really your type like Caramel or Big Mac
  86. 86.
    "Why not pursue him yourself then? You seem pretty keen on him, y'know!"
  87. 87.
    >Rarity simply tittered at that
  88. 88.
    >"Why darling, it would be uncouth to just butt in like that! After all, I'm not the one who spent the past week attached to him by the hip, am I? It's polite to let you have your turn."
  89. 89.
    >As you consider her take, you can't help but feel the tips of your ears starting to radiate heat
  90. 90.
    >You don't need to peek at yourself in the mirror to know that your face is starting to turn red
  91. 91.
    "I... I think you've given me a bit to think about, Rarity. Enjoy your eclairs, okay?"
  92. 92.
    >"Ta ta, dear! Remember, don't hesitate too much - a handsome bachelor like that doesn't stay a bachelor long in Ponyville, after all!"
  93. 93.
    >With an awkward laugh you retreat from the Boutique
  94. 94.
    >You do your best thinking down in your Party Cave
  95. 95.
     
  96. 96.
     
  97. 97.
    >With a strawberry colored mane, a buttery coat, and the worst case of anxiety this side of Applewood, (You) couldn't be anyone else but Fluttershy
  98. 98.
    >And with a deep sigh, you plop down on your favorite couch
  99. 99.
    >The past week has been a bit hectic to say the least
  100. 100.
    >You've enjoyed seeing your baby brother again
  101. 101.
    >But you haven't enjoyed seeing this side of your potential beau, Discord
  102. 102.
    >He's been trying to convince you some nonsense about how your brother isn't "canon"
  103. 103.
    >Whatever that means
  104. 104.
    >And it's made sharing time with him and your family difficult
  105. 105.
    >You think you've made some headway with the Draconequus though
  106. 106.
    >He certainly seemed to agree to ease off with the argument, if only to let you enjoy the last few days of Gale's visit
  107. 107.
    >So long as nothing else gets in the way, you should be able to happily see him off with a nice picnic
  108. 108.
    >Naturally, it's at this point that Pinkie Pie's head erupts out of one of your cabinets
  109. 109.
    >Eyes wide, expression manic
  110. 110.
    >You share a moment of awkward silence with your friend before she suddenly screeches
  111. 111.
    >"FLUTTERSHY I THINK I WANT TO KISS YOUR BROTHER"
  112. 112.
    >Oh, crumbs
  113. 113.
     
  114. 114.
    Part Two:
  115. 115.
    >It's unfortunate, but every so often traffic in the candy shop is low
  116. 116.
    >Sometimes Ponies just aren't in the mood for gumdrops and taffy
  117. 117.
    >And that's fine, sometimes it's just like that
  118. 118.
    >The slow pace of customers is enough to get your marefriend whining in your ear about taking the rest of the afternoon off though
  119. 119.
    >And as always, Lyra is persistent enough to wear you down
  120. 120.
    >(You) are Bon Bon
  121. 121.
    >At the moment anyway, there hasn't been much noise from S.M.I.L.E that requires your alter ego's attention
  122. 122.
    >And Ponyville has been blissfully content for the past week
  123. 123.
    >That's enough to get you outdoors and enjoying a lovely stroll around the village with Lyra
  124. 124.
    >Trading gossip and playful boops when there aren't any foals around to witness you being coy
  125. 125.
    >Your flirting pauses though as you notice a bit of a commotion up ahead
  126. 126.
    >A sizeable crowd of ponies has amassed around the entrance to Princess Twilight's castle
  127. 127.
    >Very peculiar, normally the resident Alicorn leaves her doors unlocked for just about anypony to trot on in
  128. 128.
    >You and your marefriend approach the crowd, parting the equine sea with ease to get to the front of the throng
  129. 129.
    "What's going on here?"
  130. 130.
    >One of the other ponies at the front of the mass acknowledges you - Time Turner, you're pretty sure
  131. 131.
    >"Well, it's just the oddest thing. There's supposed to be a tour of the Castle at this time of day - apparently Twilight managed to recuperate another section of the Golden Oaks Library's old stock and she's quite keen to show it off - but when the group arrived, they found... this."
  132. 132.
    >Time Turner gestures to the sign plastered over the great golden doors
  133. 133.
    >Paired with a massive chain and a comically sized padlock
  134. 134.
    >You read over the sign, which bears the following:
  135. 135.
    >'CLOSED FOR EMERGENCY ELEMENT MEETING'
  136. 136.
    >The simple message is enough to get a shock of concern lancing down your withers
  137. 137.
    >What could possibly be important or dire enough that the Elements need to convene like this in private?
  138. 138.
    >You can't remember them ever doing something like this for anything short of a disaster like Discord's initial return, or Tirek
  139. 139.
    >You can't help but wonder if the Princesses are in there too, strategizing with those six heroes
  140. 140.
    >Glancing around you notice the looks of unease and worry spreading on the villagepony's faces
  141. 141.
    "Well... that is concerning, but lets not get too worked up, now. Those mares have never steered us wrong when it's come to times of trouble, so there's no cause to think they will now. We should leave them to it, and hope for the best."
  142. 142.
    >Your sentiment ripples through the crowd, seeming to mollify those gathered
  143. 143.
    >'That's right...' 'Twilight will know what to do.' 'The Elements can handle it!'
  144. 144.
    >With some help from Time Turner and Lyra you're able to convince the throng to disperse and carry on with their day
  145. 145.
    >But as you and Lyra retreat from the Castle you can't help but look back at it with worry
  146. 146.
    >Maybe you should contact S.M.I.L.E
  147. 147.
    >See if they have any idea what's going on
  148. 148.
     
  149. 149.
    >Meanwhile, inside the Map Room
  150. 150.
    >Pinkie Pie urgently raps a crystal gavel on the crystal table to get you and the rest of the girls' attention
  151. 151.
    >Not that she really needed to do that, given that the five of you were already staring at her with various levels of impatience
  152. 152.
    >She'd gathered you all together quite urgently
  153. 153.
    >Literally leapt out of the bushes and foalnapped Rarity while she was having her afternoon constitution around the market
  154. 154.
    >But now that she had everyone gathered she had been sitting in her marked throne
  155. 155.
    >Seemingly waiting for something
  156. 156.
    >"Sorry girls, I was waiting for that Bon Bon opener to wrap up!"
  157. 157.
    >And we're out of the gate with nonsense
  158. 158.
    >Great
  159. 159.
    >You rest your cheek in the frog of one of your foreleg's hooves, sagging
  160. 160.
    >(You) are Twilight Sparkle, and you were supposed to be giving a guided tour of the new wing of the Library today
  161. 161.
    >The effort to find new copies of everything the Golden Oaks had once held has been a process
  162. 162.
    >Frustrating, fascinating, and especially cathartic
  163. 163.
    >You feel like a bit of your soul is being pieced back together every time you manage to reacquire one of your lost tomes
  164. 164.
    >And you had finally reconstructed the entire collection of Encyclopedias that were lost!
  165. 165.
    >You should be wowing a crowd of ponies with your array of Seapony Biology manuals
  166. 166.
    >But here we are, instead
  167. 167.
    >"Now, I'm sure you all are dying to know why I gathered you here today"
  168. 168.
    >Pinkie starts, but Rainbow Dash interrupts
  169. 169.
    >"We were dying to know about half an hour ago, Pinks, now I'm just thinking about all the flying I'm losing out on. Can we get this going?"
  170. 170.
    >You're annoyed by the sentiment but you do privately agree
  171. 171.
    >Pinkie just continues on
  172. 172.
    >"The truth is... I need your help. I've hosted hundreds of parties, dozens of Cute-ceanaras, and so many birthday bashes, but..."
  173. 173.
    >Pinkie sets down the gavel, and nervously taps her hooves together
  174. 174.
    >You can't help but sit up a bit straighter, you've never seen your friend like this before
  175. 175.
    >"I need your help to plan the perfect date for Gale. I've never planned one before! I've decided I want to kiss his face and it's gotta go just right if I want that to happen!"
  176. 176.
    >All five of you stare at Pinkie with mixed expressions
  177. 177.
    >You're taken off guard, but happy for Pinkie - you've only met Gale a few times during his stay but he seems like a solid stallion, definitely knows his way around a cumulus cloud
  178. 178.
    >Rarity is, perhaps unsurprisingly, delighted by this, clapping her own hooves together excitedly and letting out a shrill squeak
  179. 179.
    >Fluttershy can't seem to decide if she's pleased with this declaration or nervous
  180. 180.
    >Applejack shoots Pinkie a pleased little grin and lets out a folksy 'Well I'll be!'
  181. 181.
    >And Rainbow...
  182. 182.
    >"Alright, I'm out."
  183. 183.
    >The Pegasus makes a beeline for one of the doors but is stopped short by, surprisingly
  184. 184.
    >Not Applejack's lasso or your own magic (you were a bit slow on the draw)
  185. 185.
    >But Rarity's own blue magical aura, demonstrating a surprising level of strength, overpowering Rainbow as it is
  186. 186.
    >"Now Rainbow darling, please. Our dear friend Pinkie here is asking for our help! Are you really just going to abandon her in her time of need?"
  187. 187.
    >"Well, I mean, I was, but you're kind of getting in the way of that."
  188. 188.
    >Your ears twitch as you distinctly hear Applejack murmur 'Element of Loyalty my hide' under her breath
  189. 189.
    >Rainbow Dash apparently heard it too because she throws a venomous stare her way
  190. 190.
    >"I don't do dates, Applejack! What am I possibly going to add to this?"
  191. 191.
    >Rarity carts Rainbow back to her throne and rather pointedly sets her down in it
  192. 192.
    >"Now dear, just because your romantic life is shriveled up and nonexistent -"
  193. 193.
    >The unicorn pointedly ignores Rainbow's furious sputtering
  194. 194.
    >"- Doesn't mean you have nothing of value to add to these proceedings. You were foalhood friends with Fluttershy and her family, were you not? Your insight could prove invaluable!"
  195. 195.
    >Rainbow simply sags at that, conceding the point
  196. 196.
    >"Fine, but we have Fluttershy here, it's not like she couldn't make most of the same observations."
  197. 197.
    >"Perhaps, but I think you'll find that how one behaves amongst family and how one behaves around ones' friends can be quite different. Now, Pinkie, I do hate to take over this meeting of yours, but do you have any ideas of your own, to start?"
  198. 198.
    >Pinkie jolts and tugs at her loose-hanging mane, considering
  199. 199.
    >"Well... I was thinking of inviting him to bake with me, but I don't know. Does that feel like too much work? Baking can be fun, but I don't want him to feel like I just volunteered him to help me do my job."
  200. 200.
    >"Excellently reasoned, darling. Now, lets open the floor, shall we?"
  201. 201.
    >And from there the meeting truly begins
  202. 202.
    >Each mare sharing their own ideas
  203. 203.
    >Some vetoed down hard, some given real consideration
  204. 204.
    >You still think your idea of taking turns reading a romance novel wasn't really fairly considered
  205. 205.
    >And was way better than Applejack's offer of a cart ride around the Acres
  206. 206.
    >But as the night whiles on a plan is formed
  207. 207.
    >Now it's just a matter of making it happen

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