Romance for Dummies and the Otherwise Evolutionarily Hopeless

by J3sterking

Rating: everyone
Tags: Derpy Hooves, Drama, Comedy, Romance, Equestria Girls, Flash Sentry
Length: 3866

Flash Sentry had been feeling the blues for some time now. Derpy Hooves was insistent on trying to cheer him up. Almost...too insistent.

Flash Sentry was done trying to ask Sunset out. Between any number of magical threats she, and she alone, could handle, and her already busy school plate, she didn't have time to be asked out, let alone go on a date.

And throughout all his attempts, Derpy Hooves was there, ready to give him a pat on the back and a word of encouragement. But, during a conversation, Derpy lets it slip that there is another reason she was trying to help, and Flash figures it out.

This is an entry into the May Pairings Contest, being hosted by Wander D. I haven't seen any other fics with this particular ship, so I'd count it as rare enough.

Published 2024-05-14 20:10:00 UTC
Last updated 2024-05-14 20:10:00 UTC

The Klutz and the Dork

Flash Sentry sat in a cafe, tapping one foot impatiently. In front of him was a coffee, still steaming but as of yet untouched; his phone, displaying a message from Sunset Shimmer; and a rock.

He'd intended to ask Sunset Shimmer out on a date, but once again, the world needed saving. So instead of the gorgeous, flame-haired best-friend-ever, he had a small, lumpy rock.

I suppose it's technically a gem, he thought to himself. A ruby...or maybe a garnet? Regardless, he couldn't appreciate its beauty knowing that it had been about to explode less than five minutes ago.

Flash checked his phone, but he had not received a new message since Sunset's last one.

SunShim: OK we seem to be far enough apart so that the gems aren't about to explode anytime soon. I'm going to disarm mine, and then Rainbow, you can come back from Las Pegasus.

RainDash: That's great bc I left my wallet and am getting weird looks.

Flash sighed, leaning back in his chair.

The creak of leather and the clink of china interrupted his brooding. Derpy Hooves, alternatively called Ditzy Doo, Muffins, or even "Bubbles" by the other kids at school, sat down opposite him with her own cup of coffee. "Hi, Flash!"

"Hey, Derpy," he said morosely.

"It didn't go well, I take it?" she asked.

"Well, as usual, something came up before I could ask," Flash said, resting his head on one hand. "But this time, I offered to help."

"Well, that's good!"

"She told me to take this rock, and keep driving as far as possible while she ran the other direction." He spun the ruby around on the table, watching as light reflected off of it.

"Oh." Derpy stared at her coffee.

"Maybe...maybe I should just give up," Flash said. "I think it's pretty clear by now that she's not into me, or she'd have said something. I'm not even sure she's noticed what I've been trying to say." He took a sip of his coffee.

"Well..." Derpy said slowly. "If you're sure..."

"You know what? I am sure!" Flash slammed his fist into the table, bouncing the gem up into the air. "Enough of this moping around. I need to do something. Go somewhere. Be...with someone else."

Derpy shook her coffee. "Well, I could..."

"Like, seriously," Flash continued, oblivious. "To have not noticed me all this time...she's got to be blind! How absolutely thick do you have to be--"

"Flash--"

"--to not notice someone trying so desperately to get your attention--"

"Uh, Flash--"

"--when all they want is for you to notice them!" Flash finished.

"Don't say such things about yourself!" Derpy shouted, slamming her fists on the table.

Flash blinked, reeling back. Derpy glared at him, then realized what she'd said. She leaned back, face turning pink, then let her head fall onto the table, wrapping it in her arms. "Can we...forget I said that?"

"I feel like a jerk," Flash said, running a hand through his hair. "You...like me?"

"I mean...kinda? I don't know," Derpy mumbled to table. "I wanted you to be happy, so...I was trying to help you with Sunset. But..."

"That's...gotta be the most selfless thing I've ever heard of," Flash said. "Helping the guy you like...well, try to get together with another girl." He reached out, taking her hand. Derpy looked up, meeting his eyes...or, one of them, anyway. He had no idea where her other eye was looking.

"So, maybe...we could try," he stumbled. "I mean, if you wanted to, we could just...go out on a--"

The ruby on the table began to glow brightly.

Both of them looked down at it, as it vibrated ominously, before exploding in a brilliant flash of fire. Flash blinked, looking into Derpy's soot-stained face, her hair blown back, and then up to his own similar face and hair.

His phone rang, and he picked it up.

"I disarmed the gem!" Sunset said in a chipper tone. "It should no longer explode!"

"Yeah, great, thanks," he said.

"You can come back whenever," Sunset said. "Thanks, Flash. You made this way easier."

"Glad to help," he said.

"I'll let you go, now," Sunset said. "You take it easy, now."

"Sounds like you need to take it easy," Flash said. "Goodbye."

"Thanks, bye."

Flash put down the phone, looking to Derpy, patiently sipping her coffee.

"Want to go out? Together?"

Derpy spat out her coffee--which wiped the soot off Flash's face, but it was quite hot. He cried out, as Derpy panicked, reaching for the napkins and trying to shove them in his face. She, unfortunately, forgot to get up first, and only succeeded in uprooting the diner's table, crashing it into Flash's stomach, as she gasped, the table ramming into her side.

After a moment, she fell back into her seat, the table wobbling back into its place.

Flash wiped coffee from his face, rubbing at the aggravated skin with a napkin.

Derpy chuckled awkwardly, blushing. "Yes," she said, "I'd love to go out with you."

"Probably at a different diner," Flash said, looking to the other patrons and the disapproving waitress.

"I know this great place!" Derpy said, clapping her hands together excitedly. "I'll pick you up. Wednesday?"

"Sure," Flash said. "Wednesday."

It had been a while since Flash had gone on a date. But this was a casual one. Two friends, trying to see if it would work. No reason to get fancy.

Of course, that meant that he should have been anywhere but Carousel Boutique. But there he was, browsing the men's wear.

At really, really fancy suits.

"Hello! Welcome to Carousel--oh, hi, Flash," Rarity said, adjusting her 'work' spectacles. "What brings you by?"

"I just need...a suit," Flash said. "No, not--not a 'suit' suit. Just...something a little nicer than my school wear."

Rarity stared at him. "I probably have something like that around here," she mused. "Need a new Sunday shirt? I could get you something like that..."

"More of a da--" He clamped his mouth shut, but Rarity's eyes snapped towards him like a hawk. "Yeah, just a Sunday shirt," he lied.

"Are you," she said, "going...on a date?"

He looked to one side, where Lyra and Bon-bon were watching him. He looked to the other, where Trixie was pretending not to watch him. Flash sighed. "Yeah."

"With...Sunset?"

"Uh, no," he said. "Look, maybe I'll just--"

"With Derpy?" Rarity cried. "YES! YOU GO, GIRL!" She punched a fist excitedly into the air. "Hear that, Lyra? Derpy finally asked him!"

"We hear ya!" Lyra shouted. "I'll find something for her to wear!" She rushed past Bon-Bon, bowling over her friend.

"Trixie cries out--finally!"

"How long have you guys been waiting for this?" Flash asked hesitantly.

"Why, since the Friendship Games!" Rarity said. "Darling, you have no idea how painful it's been watching you three."

"Three...?"

"Derpy, and the endlessly blind Flash Sentry, and Sunset Shimmer," Rarity said slowly. "Ugh. Some people were making bets on whether you'd ask out Sunset first, or Derpy would ask you. Which means..."

"Trixie is calling Thunderlane," Trixie said. "She will have her peanut butter crackers!"

"Wait, don't--" Flash called out, wincing as Trixie, predictably, ignored him. "Please, guys, no reason to make a big deal out of this. I asked her on an impulse, it's just...casual."

"For now, darling," Rarity said.

"Rarity, for the love of God," Flash said, "I just need a nice shirt. I want to go out with a friend, and see if it works out."

"Of course, darling, we can find something like that," Rarity said. "Ooh! Lyra, what do you think their children will be named?"

Flash sighed, running a hand through his hair. It was going to be a long day.

It's a Date

Derpy held up the white dress to herself, looking at her reflection. She couldn't see it very well, and had broken the mirror ages ago, but it still helped somewhat. "Um, Lyra," she said, "I thought this was just a casual thing..."

Not to mention she hadn't even told Lyra...or invited her into her house.

"We're just all excited for you!" Lyra said. "We all know you've been wanting this for a while."

Derpy grimaced. "I mean, I have," she admitted. "But, uh...have...has everyone been watching us?"

"Of course. Your, like, two of the most popular people in school," Bon-Bon said.

"I thought she was more popular than Rainbow Dash," Lyra said. "But mostly because Rainbow Dash thinks she's good at everything."

"Well, she is," Derpy said.

"Honestly, that just makes it worse," Bon-Bon scoffed. "Like she's judging you for your every flaw."

"Like you feel so inadequate when she's around," Lyra agreed. "Like your every flaw is just highlighted for everyone to see."

"Really? I have lots of flaws, but I've never felt like that," Derpy said, holding her chin in thought. Why was that?

"W-well, you should try on the dress," Bon-Bon said.

"I don't know," Derpy said. "I never feel right accepting Rarity's gifts."

"She lives to give, D.D," Lyra said. "Don't worry about it."

"Well, alright," Derpy said. "But I don't want to pressure Flash."

"Oh, don't worry. Word on the street is he was getting dressed up, too," Bon-Bon said. "He had Rarity get him dressed in his Sunday best."

"Really?" That was something she hadn't expected. Maybe she'd accidentally stressed him out and he was trying to over-compensate?

"Really really," Bon-Bon said. "So quit worrying about it! Just put it on!"

"Okay...here we go." She began pulling off her shirt, but the doorbell rang.

"Oh, shoot! He's unfashionably early!" Lyra gasped. "You get dressed, I'll distract him!"

"Why distract him?" Derpy asked, but Lyra was already out the door.

Flash had, in the end, pulled his second-best shirt out of his wardrobe. Rarity had foisted a ridiculous, three-piece suit with diamonds sewn into the fabric--a technique she had learned from her inter-dimensional doppelganger.

Flash had only a couple of talents. One of them was knowing when it was too much. He'd gone for a simple leather jacket and somewhat fancy-looking shirt. He had put a rose in it, and that was the only concession Rarity was getting.

He knocked on the door. He heard muffled shouts--which was odd, because he thought Derpy just lived alone with her mother.

Lyra Heartstrings opened the door.

"Oh, hi, Flash, what's up?" she said, with the fakest grin he'd ever seen plastered on her face.

"Nothing much. Just going to take Derpy on a date." He raised an eyebrow. "Which you knew about?"

"Whaaaat? How would I know that? Am I psychic like Pinkie--"

"Not psychic!" Pinkie Pie shouted from inside.

Lyra jerked her head, looking over her shoulder, then turned back to Flash. "So," she said. "How've you been?"

"Better that I quit moping about Sunset, worse with a certain someone blocking off the doorway to my date," he said. "Should I...just leave, then?"

"No, no, no--she's waiting on you!"

"Then can I come in?" Flash asked.

"Never!" Lyra declared.

"Lyra," Flash said, patience thinning. "What is going on?"

"Oh, nothing."

"So let me in."

"No."

Flash face-palmed. "Okay, look. I asked Derpy on a date, right?"

"Yeah, we both know that."

"So, we are going to go, together, to a pre-determined place to hang out," he said.

"I know what a date is," Lyra snorted.

"So, I should say hi to her, greet her, and then take her out," Flash continued.

"Yeah, of course!"

"So can I come in?"

"Never in a million years," Lyra said.

"Okay, I'm dressed!" Derpy called out.

"Thank God," Lyra whispered, stepping aside. Flash stepped past her, looking to Derpy.

And his jaw dropped to the floor.

Derpy stood, hair done up. She wore a beautiful white dress, with a golden lacing along the bust and sleeves, and down to the waist. The skirt came down to her ankles, where diamonds swung gracefully. Around her throat was a beautiful diamond necklace.

"Where in the hay did Rarity get all these diamonds?" was the first thing out of his stupid, traitorous mouth.

"I think from Equestria?" Derpy said, looking down at herself. "Hope she doesn't crash the diamond market."

"Eh, it's all inflated prices, anyway," Flash said, scuffing one shoe against the floor.

"Whatever happened to your Sunday best?" Bon-Bon asked, peeking from behind Derpy.

"I said 'just a Sunday shirt'," he said. "And then Rarity held me hostage until I accepted a five-hundred dollar suit."

"So...you want to just be...casual?" Derpy asked.

"Of course. That...I'm going to be honest, that hardly looks like you," he said. "I'm fine with you, however you look."

Derpy let out a sigh of relief. "I'm glad. I don't think those diamonds would survive the night."

"Wait, what are--"

Derpy grabbed the dress by the throat. Lyra screamed, jumping and tackling Flash. Being half his size with the build of a malnourished willow, she bounced off and merely clung to his shoulders.

Derpy ripped the dress off, revealing shorts and a tank top beneath, as well as impressively muscled arms. In the far distance, Flash heard Rarity let out one of her patented shrieks as Derpy gave the dress to Bon-Bon, then shook her hair loose. The pins fell to the floor, clattering.

"Give me a second to get my biking jacket!" Derpy said excitedly, closing the door to her room. It slammed shut on Bon-Bon's hair, but leaving her trying to tug it free fruitlessly, unwilling to drop Rarity's expensive dress.

Derpy bounced past, running to a closet and pulling out a black leather jacket. She slung it over her shoulders, then handed Flash a men's necklace.

He held it up, looking at the topaz in it.

"Rarity gave us matching necklaces," Derpy explained, pointing to her diamond one. "Lyra told me to give it to you."

"You weren't supposed to tell him I told you to!" Lyra said.

"Oh. Well, someone told me to give you that necklace," Derpy said with a smile.

"Oh, thanks," Flash said. "It's nice." Wow. Smooth like jazz, ya moron, he thought angrily at himself.

"Well, come on!" Derpy said, pulling him towards the door, oblivious to Bon-Bon's attempts to free herself.

Flash followed her, as she walked him past his car. "Wait, I thought we were taking my car," he said.

"Silly, I can't drive a car," she said.

"I mean...I figured, but I can," Flash said.

Derpy laughed. "No, Flash, I'm driving," she said. She picked up a bicycle with an oversized basket on the front. She sat on it, then beckoned him over. "Come on! Buckle up!"

"Um--how about we just take the car?" he suggested again. "I don't think bicycles are meant for two people."

"Just grab onto me!" Derpy said. "You have three feet of me to choose from."

"Um--" Flash did the smart thing, and shut his mouth before he could make any more stupid comments that evening. He got on the bicycle, behind Derpy, and put his hands around her waist.

Derpy paused.

"What?" Flash asked.

"You've got nice calluses," she said. "Do you work out?"

"Um--no?"

"Huh. Must be the guitar." She rang the bike's bell, saying, "Buckle up, bronco!"

Flash had been prepared for many things, including them going off balance and careening into the bushes. He was not prepared, however, for the bike careening over his car, onto the road, and screeching down the street with the sound of burning rubber.

"Um, Lyra?" Bon-Bon called out. "Can you help?"

Lyra stepped over, then tried the door. "Uh, it's locked."

Bon-Bon tugged at her hair, then sighed. "Can you fetch my lockpicks out of my purse?"

"Sure. Where'd you leave it?"

"In Derpy's room." They both looked to the door, then, as one, sighed.

The Two of Us

Derpy's bicycle skidded to a stop, landing perfectly into the bicycle parking. "Here we are!" she said, climbing down from the bike.

Flash shook himself, then got down after her, wobbling unsteadily. Rainbow Dash's magic necklace had nothing on how fast that ride had been.

Flash brushed a stray, blonde hair off his shoulder, then stared up at the building in front of them. "Derpy, is this..."

"My favorite place to eat out: Rise N Shine Bakery!" she said proudly.

Flash stared at it in surprise. Well, it wasn't the weirdest place he'd gone on a date, but he'd yet to meet someone who suggested it first.

Derpy looked at him, confused. Did I do something wrong? she thought. She hadn't gone on a date before. Lyra had just said, "Take him somewhere nice," and, as usual, forgot to follow up with anything more specific.

And Derpy had never been smart.

Flash chuckled, thankfully. "Alright," he said. I mean, I can't think of anyone who doesn't like pastries, he thought. Maybe a bakery was a better first date location than he'd have thought.

The two walked into the Rise N Shine. Flash considered taking her hand, but...he didn't want to come across as too forward. She might think it creepy. He instead looked around the bakery. He'd been in here before, but Sugarcube Corner was his normal haunt, though Sunset had never liked eating--

Again with Sunset, he thought. She's not here, and not interested. Derpy is interested...and I've got to admit, at this point, I am, too.

He's not taking my hand, Derpy thought to herself. I thought he'd want to, but...is that too forward? Oh, why don't people come with manuals? Derpy had never been able to read the room, or 'get a clue', and still wasn't sure why they called it a 'poker face'. Were there things she wasn't getting? Was the girl supposed to take the guy's hand?

I should have asked for more details, she thought.

Flash lead the two to the counter, examining the menus he hadn't seen in months, at least. She's being quiet, he said. Did I do something? Truth be told, Flash hadn't gone on as many dates as people had assumed. Being popular was one thing, but he'd never just accepted dates from random people he barely knew.

Aside from Sunset, who had apparently been a unicorn from another dimension.

"Hey, Derpy," the woman behind the counter said. "Been a while, huh? What can I do for ya tonight?"

"Well," Derpy said, "how about a dozen of the regular, to share. And Flash? What do you want?"

"Well," he said, thinking, "let's get some donuts, and share those, too."

"Okie-dokie!" Derpy said. "A dozen of those, too!"

"That's a lot of pastries," Flash muttered.

"Oh, um..."

"No, no, it's fine!" Flash said. "We can just pack up anything we don't eat." I have got to learn when to shut my mouth, Flash thought to himself.

Maybe the Rise N Shine was a bad idea, Derpy thought to herself. I need to be careful not to ruin this for him...

The two sat down with a box of donuts, and a large basket of muffins.

Flash took a muffin, and Derpy took one of the donuts immediately.

"You come here often?" Flash asked.

"Well, I used to," Derpy said. "I haven't been in a while, though."

"Why not? Seems like you like the place."

Derpy sighed. "Yeah, but I accidentally broke the kitchen, so I'm helping pay for that." She stared at the donut, almost forlornly.

"You broke...the kitchen?" Flash asked. "You mean, like, the countertop, or--"

"I accidentally hit the island, knocking it into the stove," Derpy explained. "Mom was upset. Her pie was fine, though."

Flash stared. "Wow. That's a huge cabinet, and you just...threw it into the stove?" FIND YOUR FILTER, MAN!

Derpy nodded. "I'm really strong," she said. "I break things all the time, but normally smaller stuff. Less expensive stuff."

"Oh. Well, uh...sorry to hear that."

Derpy stared at the donut. "I break lots of things," she said.

"I like buying unnecessary and expensive things," Flash replied.

"I can't drive a car."

"My only real talent is music, and that's only so-so," Flash said.

"I have lots of doubt problems," Derpy said.

"So do I," Flash said. "But...you..."

"You deserve better than me," they both blurted out.

There was a pause. Then, Derpy laughed. A wonderful, musical laugh that wrapped up Flash and brought him along for the ride.

They laughed for a good long time. "I don't want better than you, though," Derpy finally said, wiping tears from her eyes.

"I just want you," Flash agreed. "I was...a little on the fence about it. It was really sudden, you know? A random, spur-of-the moment choice. But...I'm glad I made it. You're a wonderful person, Derpy."

"I...I am?"

Flash chuckled. "Of course. How many other people would be sitting there, helping the guy they like try to get together with someone else? How many other people would still be around after so many klutzy mistakes? How many other people could smile like you do? So sincerely...so nice."

Derpy frowned. "Well, um...you're wonderful, too. How..."

Flash waited patiently.

"How many people, could, uh...play the guitar like you do?"

Flash sighed. "Rainbow Dash," they both agreed.

"Hold on," Derpy said. "Um, oh! I got it! How many people would keep going after being rejected over and over again by the same woman?"

Flash paused. "Well, yes, but you don't have to phrase it like--"

"How many people are so nice they become the most popular person in school? How many people keep going after things don't work out, again and again? Just...keep fighting. Keep being you. Keep on...keeping on." Derpy smiled.

Flash smiled. "Thanks. It'd have been better if you hadn't taken two tries, but...still. Thanks." He smiled, picking up a muffin.

It took him a second to realize they were out of muffins. He frowned, looking at the empty box, then looked up to Derpy, who was chewing happily. She looked at the empty box, swallowed, then gasped. "Oh! Sorry, did you want another?"

"How in the..."

The earth shook. They both jumped up in alarm, as the windows rattled.

"Earthquake!" Flash yelled.

Derpy seized him by the front of his jacket, pulling him closer, and kissed him. Flash froze, unable to move, as a rainbow blast shone outside, along with the distant cry of, "Friendship is ma-gic!"

After a long moment, Derpy let go, blushing. Cheers rang up from the other customers as Flash ran a hand through his hair.

"I, uh...it felt right," Derpy said.

Flash grinned. "Same time, next week?"

Derpy nodded. "Yes." She took his hand, holding it in hers, and added, "Thanks for giving me a chance."

He kissed her, catching her off guard. "Thanks for everything," he told her.

Author's Note

And here we are. It's been a while since I wrote romance, but I think it turned out okay. Drafts alternated between hyper-fixating on both of their insecurities, or just being completely comical, but in the end I decided upon this mix of the two. Anyways, I hope you enjoyed! I will be getting the next chapter of Cyberpony: Y2K out this evening or early tomorrow, and I wish you all good evening.