Of Challenges and Kisses

by RavensDagger

Chapter 1: Challenge Set

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Featherweight sat on the schoolyard’s green grass. His cream-coloured ears perked towards his friends, while his eyes stared at three talking fillies.

The three fillies--a pegasus, a unicorn, and a small earth pony--sat around huddled, talking and drawing crazy plans in the sandy ground. One in particular drew his attention.


Celestia, she’s pretty, he thought with a sigh.

Scootaloo stood over the other two, wildly gesturing a masterful plan that was certain to either get them their cutie marks, or land them in a hospital. Her two friends alternated between looking at her in disbelief and giving each other small, uncertain stares.

Something nudged against his leg with a small crunching sound. Turning, Featherweight sighed again as he looked at his own two friends’ expecting faces.

“Oi, are you even listening?” asked Pipsqueak, a sheepish smile spread across his small features.

“...And then she said it stood for Prissy Mare Syndrome. I think she was lying,” said Chowder, unaware that the other two colts were not paying attention to him. Suddenly the pot-bellied colt stopped, looking at his two friends as they stared at each other. Shrugging, he reached a hoof into his saddlebags, pulling out a wrapped granola bar and tearing through the wrapper loudly before chewing on it. He stared at them blankly, mouth moving up and down as he chewed.

“You were looking at her, eh?” Pipsqueak nudged the pegasus colt on the shoulder again.

Featherweight stiffened. He knows?! His face reddened violently as his friend began to chuckle.

“You were looking at her!” The smaller colt leaned in, whispering secretly. “You like her, don’t you?”

“Well, no, I-I mean,” his voice trailed away into an almost imperceptible whisper, “Yes.” The three boys sat there, two of them staring at Featherweight while he shifted about on his hooves. The wind caressed them as it blew the sound of songbirds around the schoolyard, the noise almost drowned out by the playful shouting and screaming of the other foals.

“Well,” encouraged Pipsqueak as he tried to break the silence. “Aren’t you going to do anything about it?”

“Yeah, you need to tell her,” said Chowder between mouthfuls of granola, little pieces of the candied bar spraying about between gulps. “If you don’t, you’ll regret it forever, then you’ll get fat and marry somepony you don’t love. Least, that’s what my father said.”

Featherweight gulped under the pressure of his two friends. “But, what should I say? I-I don’t really talk to girls much...”

The school’s bell rang, loud and clear as it struck a note familiar to everypony nearby.

The three jumped. “Come on children, class is about to start.” exclaimed the cheerful voice of Miss Cheerilee. The teacher stood halfway out the schoolhouse with a tiny brass bell held in a forehoof. She smiled broadly as the foals began to trot into the small, rustic building.

Featherweight let out a small sigh of relief as they began making their way into class. The relief however, was short-lived as Scootaloo placed herself right in front of him in the jostling line of foals entering the school. She fluttered her wings anxiously and smiled happily as she chatted to her friends. Don’t look at me. Don’t look at me. Don’t look at me, he repeated in his mind as beads of sweat began to form at the edge of his scalp. The pegasus’ pink tail swished in his face momentarily, making him gulp audibly. For a few seconds his brain backfired, rendering him thoughtless and numb.

A white hoof landed on his shoulder, making the young pegasus jump in fright. Looking to his side, he saw Pipsqueak’s confident smile. “I bet you can’t do it.”

“Do what?” he asked, his hoofsteps clacking against the schoolhouse’s wooden entrance. Inside, a cool wall of air met him and sent small shivers down his already excited spine.

The interior was organized chaos. Paper covered desks that were in neat little rows, accentuating the rustic feel of the little classroom. At the front was a simple wooden desk, adorned only with a fresh red apple and a few notebooks.

Pipsqueak and Featherweight found their way to the back of the room through the bustle of moving foals, sitting beside each other on well-worn benches. “You know, I bet you couldn’t snog her,” his friend whispered.

“What?!” Featherweight’s eyes widened and his ears perked up as he stared at his friend.

“I said could you all take out your textbook and turn to page seven,” said Miss Cheerilee, who sat at the front of the class. Moments later the sound of pages rustling filled the room.

Featherweight looked up, noticing that more than one set of eyes were on him. One set, violet in colour, really drew his attention. “Um, thanks, Miss...” He smiled sheepishly and flipped his book open to a random page. The kind teacher gave him a knowing smile before she resumed her lesson. For a few seconds, the only sound was the clacking of chalk on the blackboard.

Minutes of blindly listening to the tales of ‘Inky the Bold’ later, Featherweight received a poke on the shoulder. Looking down, he noticed a small, crumpled-up ball of paper laying at the foot of his chair. Slowly, so as to not be noticed, he leaned over and grabbed the paper, stuffing it in the cracks of his notebook.

He unfurled the paper, cringing at every crackle it made until finally it opened. He read it in a low whisper, “I’ll bet my signed Spitfire poster that you can’t snog her by the end of the day. --Pip”

Featherweight’s jaw dropped. That Spitfire poster was not only beautiful, it was signed by somepony who was quite possibly the best flyer ever! Shutting his mouth, he gulped, peeking at Pipsqueak’s giggling form beside him. For the second time that day his mind went blank as he imagined the implications. Not only could he get his hooves on the precious poster, success would also mean that he would get to...

“Who do you want to be with, Featherweight?” a smooth, motherly voice asked.

“Scootaloo,” he said absently, still looking at the note.

The eerie silence of the classroom was the first thing that notified him that something was wrong. Slowly, he lifted his head, looking at the other students.

Everypony’s eyes were staring at him. The most attention grabbing of them belonged to Scootaloo and her two inseparable friends. Miss Cheerilee shifted her weight as she stood nearby. “You want to work with Scootaloo? Fine.” A tiny smile escaped the teacher’s lips.

Blushing madly, Featherweight looked at the blackboard. ‘Special biology project!’ was written across it in the teacher's usual bubbly hoof-writing. “Um, yeah,” he said, his blush deepening on his beige face. “We’re both pegasi. you know, wings and all that...” His hoof traced a small circle on the wooden desk.

Miss Cheerilee perked up. “That’s an excellent idea! How about everypony works with somepony like them?” The teacher spun around, heading towards the front of the class, pointing from student to student making pairs. “Okay children. This project is simple,” she said as she faced the class once more. “The goal is to point out a few interesting aspects of the species you picked. Now be as specific as you need to.”

Cheerilee grabbed a piece of chalk and began writing on the blackboard while she talked. Featherweight quickly pulled out pen and paper before he began scribbling notes.

“That was smooth,” whispered Pipsqueak under his breath, interrupting the pegasus’ concentration. Featherweight dropped his quill to shoot a glare at his friend, only to have his attention stolen by Scootaloo. One of her eyebrows was perked up and her head slightly tilted to one side. Sweet Celestia, she’s looking at me! his mind screamed.

He gulped before giving her an awkward smile and a tiny, almost imperceptible hoof wave.

She smirked back, teeth gleaming brightly as they caught the sun , cheeks puffing out while her face contorted into a big grin.

His heart melted. Slowly and forcibly, he turned his head back towards the front of the class, not daring to look anywhere but the blackboard as the heat on his face slowly dissipated.

“Okay class, I expect that group project on Tuesday. That only gives you four days!” said Cheerilee as the students raced to pick up their things. Featherweight hurriedly swished his wing across the desk, sending all of his notebooks into his open bag before bolting for the door.

Leaning against the school’s wooden door was Pipsqueak, Chowder only a few hoofsteps behind him. “That, Featherweight, was awesome!” squeaked the little colt as he tapped his friend on the back.

“Yeah... awesome.” Featherweight stumbled out of the building, his little wings fluttering before he landed on the soft grass.

“No, really, that was cool!” said Chowder, stuffing his face with hickory chips. “Takes a brave stallion to confess so publicly.”

Featherweight’s eyes widened to the size of saucers. “Confess?!” he yelled, then whispered as he noticed the eyes of many on him. “Confess? I didn't do that, did I?”

Pipsqueak trotted up beside him, hopping on the spot to adjust the height of his saddlebags. “Not really, but anypony that can read between the lines.”

Featherweight moaned helplessly. “I’m so doomed.”

Pipsqueak nudged him. “Don’t worry. Chowder and I will help you out!”

The little pegasus looked up, suspicion written all over his face. “What would you two know about ‘snogging’?”

The little spotted earth pony open his mouth to speak, but stopped when his eyes locked on something behind the pegasus colt.

Turning slowly, the colt gulped as he saw the three fillies that had gathered behind him. “Hi, Featherweight,” called Scootaloo, waving. Behind her, Sweetie Belle and Apple Bloom shot him an distrustful glance.

“Oh, um, hi Scootaloo,” he said, almost shaking as his nerves rattled. She’s talking to me. Oh Celestia, she’s talking to me!

Scootaloo didn’t seem to notice. “I was wondering if we could work on the project today? Me and my friends are going crusading this weekend so we don’t have much time. Are you free?” The filly tilted her head to one side while looking at him inquisitively.

“Of course I am!” he answered a little too loudly. Bringing his voice down he repeated himself, “Yeah, I’ve got all night.” Several eyebrows rose.

“Great!” said Scootaloo, turning as she addressed her friends. “I’ll see you guys later, alright?”

“Alright Scoot, we’ll be over at Sweet Apple Acres when yer done!” Apple Bloom said as she turned around and began trotting away.

Sweetie Belle’s eyes shifted between Scootaloo and Featherweight before she too began trotting away, muttering something about ‘Rarity warned me about this’.

Scootaloo watched as her friends trotted down the well-paved road where other fillies and colts played. “So, where do you want to start?”

Featherweight stared at her blankly until Pipsqueak spoke up. “Why don’t you two go to Featherweight’s place? His parents work ‘till late so you’ll be all alone to work on the project.”

“Cool, hopefully we can get it over with tonight; these projects are such a drag.” Scootaloo turned, hooves crunching against the gravel road that lead to Ponyville.

“Okay,” whispered Chowder as he snuck in beside his pegasus friend. “Make sure she knows that you’re better than her at everything; it’ll impress her. And they don’t like it if you’re too fast. Oh, and check your breath before kissing her; if it stinks she’ll say no,” the chubby pony counseled wisely.

“Stay close to her at all times!” added Pipsqueak.

“No actually means yes.”

“Cider makes everything better!”

Featherweight fluttered up into the air, floating a few hoofsteps up while he placed his forehooves against his temples. “Okay, okay, I can handle this... No, I’m going to die.” He began hyperventilating, chest heaving and puffing in an uneven rhythm.

“Aw, don’t worry,” said Pipsqueak, pushing the hovering pegasus towards the young filly. “Just be yourself; you’ll be fine.”

Gulping once more, the little pegasus fluttered after Scootaloo, flying past the schoolhouse and the other fillies and colts who were still playing. “C’mon Featherweight, I don’t have all day,” she yelled. Without hesitation, he redoubled his efforts and sped up to her, landing at a trot beside the walking filly.

For a while, they both walked beside each other: he, pointedly looking at everything but her, and she, glancing around in a carefree fashion, her eyes often pulling upwards towards the deep, blue sky.

“So,” she broke the silence as they walked into the town proper.

She’s talking to me; she’s going to ask me a question. He snuck a quick peek at her wide expecting eyes, then refocused on the road ahead. I can do it. Just think, and don’t say anything stupid.

“Where do you live?”

The tension that had been building up in the little colt deflated almost immediately. “I live behind Sugarcube Corner, not far from the town hall,” he said, picking up a little confidence when he noticed that his voice didn’t shake.

“Oh, that’s cool,” the little pegasus said with enthusiasm. “Rainbow Dash’s house passes over there every Tuesday.”

Featherweight was taken aback by the sudden comment on Rainbow Dash, an eyebrow rising in surprise and exclamation. “You really like her, don’t you?”

Scootaloo stopped where she was, staring through him, eyes filled to the brim with adoration. “I love her! She’s so cool, those powerful wings, her awesome mane. Oh, and those epic eyes... I could stare at them all day long.”

Featherweight could sympathise as he looked to her with the same level of adoration.

“Should we keep going?” he finally asked, immediately regretting it as she shifted her attention elsewhere.

“Yeah, sure!”

Featherweight smiled shyly before leading the way, twisting and turning amongst the town’s roads. Relaxed ponies trotted around, chatting or minding their own business as they went about their routines.

“Here we are.” Featherweight stepped up to a small house that was squeezed between two shops. One of the shops had a dangling sign proclaiming that it sold the best cameras in Equestria. Hopping forward, the colt pushed the handle with his muzzle, twisting until the door clicked open. “Welcome to my home,” he said, stepping aside to let the filly in.

A quizzical brow rose up as she trotted into the home. “This is nice,” she said, looking at the white walls adorned with dozens of hung picture frames.

“Thanks! My dad owns the camera shop next door. We take a lot of pictures.” The colt squeezed past her, trotting down the narrow corridor that led to his room, blinking his eyes to adjust to the house’s yellow light.

Scootaloo followed him as he opened the door that led into his little room.

“Wow, this is cool,” she said, throwing her saddlebags to one corner before spinning a tight little loop as she took in the entire room.

Every wall was covered in pictures. Not a centimeter remained that did not have a colourful image of something, from ponies doing silly things, to pictures of nature and greenery, to images of his friends. In one corner, standing out because of their stark colours that meshed badly against the colourful walls, was a bed and a desk.

“Do... do you like it?” he asked, fumbling with his hooves self-consciously. She didn’t notice as her eyes wandered the room, looking from one image to the other.

Suddenly her ears perked up. “Hey! We could use pictures for the project.”


“Yeah, you take pictures of my wings.” She fluttered her little orange wings, sending a small draft of wind around the room. “And we could use them in the project! It’d be awesome.”

A thin smile crossed his face. “Sure, I’ll prepare my camera!” Maybe this won’t be that bad. All we need to do is take a few pictures of our wings while she’s in my room the-- His heart stopped and his mane stood on end as he rewinded his thoughts. She’s in my room. Gulping, Featherweight turned, looking at the filly who was staring at one of his picture-covered walls.

That particular wall had images of school, a school that she attended. Images of Scootaloo outnumbered everypony else’s. “I’m ready!” he suddenly exclaimed, swiping the camera off his desk before dashing between Scootaloo and the images. Sweat poured freely from beneath his mane, plastering the edges of it against his forehead. “Whew, a little hot in here, huh?”

“Um, yeah?” Scootaloo tilted her head to one side, her hair cascading down with a slight rustle as she examining him closely. “Should I open a window?”

Featherweight sighed inwardly. “That’d be great! Just turn the knob, I’ll put a new reel of film in.”

While the young mare turned to spin the window’s cranky knob, Featherweight ripped as many images of her off the wall as he could, grimacing as they tore audibly. Thinking quickly, he threw them under his bed, pulling out a poster of the Wonderbolts.

Just as Scootaloo was about to face him, he slammed the poster onto the wall with a swift kick. “Thanks for opening the window, it’s much better now!”

“No problem. Now, let’s get this over with, alright?” the orange filly trotted to the middle of the room, standing there staring at him while he fretted with his camera. “You going to take pictures, or what?”

“Um, yeah,” said the colt, stepping forward he lifted up his camera and pressed its button. A loud click went off as it flashed brightly in the room. Moving around her, Featherweight snapped image after image.

“Should I stretch my wings?” she suddenly asked, snapping him out of his reverie.

“Stretch your wings?” he repeated in a daze. Misunderstanding him, the little pegasus unfurled her wings with a light snap, keeping them straight along her sides as each individual feather reflected the sunlight that poured through the open window.

Leaning forward, Featherweight looked down the objective of his camera, quickly snapping image after image of the little mare’s wings. His face flushed a deep red as he approached her; she smelt of a summer breeze.

Each individual feather preened as he approached, their glossy orange brighter than anything in the room as he stared at them lovingly. “They’re beautiful,” he whispered.

Scootaloo tucked her wings back in. “What did you say?” she asked, turning to face him with her wide violet eyes.

“I-I said, um...” I can’t lie to those eyes, he thought as the filly’s stare pierced his soul. “I-I said that they’re beautiful.” He coughed lightly, turning away from the filly to stare out the window. He kicked the ground lightly, scuffing the floor absentmindedly as his face burned.

“Oh,” she said, her own orange face becoming a deep red. “Well, um, thanks.” The filly’s eyes met his own, both of them staring at each other for a few seconds that felt like hours to the colt.

Featherweight broke the contact, coughing awkwardly before doing a half turn towards the entrance. “Maybe, maybe I should get us something to, um, drink?”

“Yeah, that'd be great!” she exclaimed, relief plastered all over her face. “I’ll start on the written part of the project.”

Featherweight trotted out of the room and into the corridor that bisected his home. His wings twitched self-consciously as he made his way towards the kitchen. Stupid, stupid, stupid! Why am I so stupid?! I should have just shut up. Gah, I’m so doomed, he berated himself while pulling at his mane.

In the small kitchen he made a beeline for the fridge, opening it and searching for drinks. Quickly, he pulled out a jug of lemonade and two glasses from a nearby cupboard. Placing his hooves on either side of the filled cups, he bowed his head. Okay, Featherweight, you can do it, just go in there and act normal.

Pushing himself away with a sigh, he placed the two glasses on a tray that he balanced on his back before walking out of the room.

“I’ve got lemonade,” he said as he walked into his room.

Scootaloo had her back to him, hunched over his work desk that was covered with papers and her opened saddlebags. Trotting forward, he deposited the tray on the edge and glanced over her shoulder. “Wow,” he gasped.

In front of the little filly was a hoof-drawn diagram of a pegasus’ wing, each and every little bone and ligament present and labeled. “That’s incredible!”

Scootaloo blushed a little. “Really? I just know about wings...”

Featherweight leaned over her, inspecting the image. “No, really, it’s awesome! How come you know so much about wings? I could hardly name half of these.”

The filly reached over, grabbing one of the cups and sipping from it audibly. “Well, I’ve always been fascinated with flying. you know, Rainbow Dash is really good at it, and I wish I could fly as good as she does, so I studied it a bit.”

Featherweight looked up from the image. “What else have you done?”

The filly reached out and pulled a thick book from her saddlebags. “Well, I thought that we could use some of the things in our manuals. Maybe expand upon them. I was sorta surprised at how there isn’t much about pegasi in here, really. It hardly covers flight, bone structure or even our inherent magi--” Scootaloo stopped, blushing self-consciously as she slowly turned towards Featherweight. “I mean...”

She’s even cuter when she’s smart! And she’s shy about it, Featherweight gushed in the privacy of his own mind. Coughing lightly, he got his thoughts straight. “So, where should we start?” he asked as he walked around the mare, flipping through the pages of the textbook until he found a section that spoke of pegasi. “Mmm, how about we focus on flight? You seem to know a lot about it and I can take pictures and document ponies in flight!”

Scootaloo seemed to overcome her apprehension as he excitedly looked over the project. “That’s a great idea! Oh,” she said, eyes filling with adoration. “Maybe we could get Rainbow Dash to help us!” The filly began quizering with anticipation.

“We don’t need her, I’m sure you’re an excellent flier!” Featherweight gulped as he realized his mistake. Scootaloo looked down in shame, a warm heat radiating from her face as she did so.

“Not really, I-I suck at it.” She sighed. Suddenly, she looked up and out the room's only window. “It’s getting late,” she said, staring at the orange sky where the sun was beginning to dip below the horizon. “I should get home.”

With the sound of the wooden chair scraping against the linoleum floor, she leaned over and grabbed the sheets of paper, throwing them into her saddlebags. “Thanks for the lemonade.” Scootaloo began walking out of the room.

Darn it, darn it, what did I do? Gah, I’m such an idiot!

Arriving at the front door, the little pegasus filly turned around. “Well, this was really fun, Featherweight. I’ll be back tomorrow?”


“...You know, to finish the project?” She smiled kindly at him.

“Oh, right!” He smiled back, blushing awkwardly while rubbing a forehoof behind his head.

Scootaloo nodded formally before opening the door and hopping out.

She... she left...

“Wait, Scootaloo!” he screamed, hooves clacking against the floor as he rushed out.

Outside, the orange filly stood on the edge of his entranceway, her coat glowing in the warm rays of the dying sun as the empty street whistled the desolate song of sleepy birds. Sweet smells from the bakery next door filled the air with an odor that left them hungry.

“You, know... about flying, maybe I could, um, teach you?” he said, turning his eyes away from her. “I’m not all that good, certainly not a Rainbow Dash, but I can manage, and mayb--” His words cut off as the impossible happened.

Scootaloo hopped towards him, leaning forward to give him a hesitant peck on his upper cheek. “Thanks, Featherweight, that’d be nice,” she said, both of them blushing heatedly.

“I-I, um, it’s, er--” Featherweight fumbled with his words as she stepped back onto the street, the lights casting her in a warm orange glow.

“See you tomorrow!” Scootaloo called back as she galloped away, a silly grin on her small face as the sounds of her hoofsteps faded.

“Yeah, tomorrow,” he repeated, eyes glazed over as a hoof rose to touch his cheek. A strong burning sensation still tingled where his hoof touched. “Tomorrow...”

Hours later, when many a light was off and the entire town was covered in a shroud of darkness, only illuminated by the bright moon overhead, a certain beige pegasus sat in front of his house, the largest and silliest grin adorning his face. “I‘ll see her tomorrow,” he whispered into the night.

Yeah, yeah... Not my usual ordeal. No death or plagues or globe controlling empires bent on the destruction of X... Call it practice, this time of cutesy wusty D’aww stuff...

Edited by the great, powerful and marvelous Arcainum and N!
Proofread by Bearycool And Frederick the Saiyan!

The author is some dufus called RavensDagger who promised that he’d be working on this, instead.

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