The Dare
Fluttershy eyed her childhood friend dubiously. "'Awesome cool?' Sure. But 'devastatingly handsome?' I don't know. Maybe?"
Rainbow Dasher fluffed up his feathers. "Rainbow Dasher is so cool, he can do anything! Fly faster than anypony in the world. Do a sonic rainboom! Clear the sky of clouds in ten seconds flat."
Fluttershy leaned back against a high spot on the cloud where the two friends rested. "But you said you're the most attractive pony in Ponyville. And those other things you said might be cool, but are they the same thing?"
"Hay! Nothing says handsome like Best Pony does. And anypony who can do all those things is obviously Best Pony. QVC!"
Fluttershy nibbled her own lower lip thoughtfully. "I think attractiveness is shown by...attracting. Come on, let's go down into Ponyville." She leaped off the cloud, flying to the town below. Rainbow followed.
***
"This park should be a good spot to test your claims," Fluttershy said. "Now...start attracting."
"What?" Dasher asked.
"Prove how attractive you are." Fluttershy gestured at the park with one wing. "This park has lots of ponies, having fun or just hanging out. Do your 'romance magnet' thing or whatever."
Rainbow's brows rose skeptically. "Fluttershy...this doesn't really seem like you. Usually you aren't so...assertive. So demanding. So--"
"Ready to call you on your bragging?" Fluttershy smiled. "I just felt like trying something different. And besides...doesn't this sound like fun?"
"I guess?" Rainbow's head tilted. "Hay! You over there!" He pointed at a mare. "Don't you think I'm really handsome?"
A prismatic-maned mare turned around. "Oh, HELLO Dashie! Of COURSE you are! You're the most handsome, best looking, and generally awesome pony in all of Equestria!"
Fluttershy shouted, "Asking your MOM doesn't count! And what's she doing here in Ponyville anyway?"
"I didn't know it was my mom!" Dasher protested. "It was a coincidence!"
Windy Whistles grinned at Fluttershy. "Just delivering some Wonderbolts fan club posters, as part of my new part time job. And hay..." She trotted up to the two friends, and pulled some spectacles out of her saddlebags. "Here, Dashie, you forgot your glasses and left them at home." She embraced her son with one wing. "I thought maybe you would come back to pick them up again...but I guess not."
"Thanks, Mom," Dasher said resignedly. "You're the best mom a stallion could ever have. But, um...Fluttershy and I are playing a game that might work better if my mom isn't here."
"You don't want your mother cheering you on? Helping to raise your spirits? Making sure everypony knows just how awesome you are?" Windy gave Rainbow a disappointed look, tears pooling in her eyes.
"There are some things a pony just has to do on his own. By himself."
"But Fluttershy can still be here?"
Rainbow scuffed the grass with one hoof. "Fluttershy knows how to be quiet. And she doesn't make me nervous while I'm trying to do...what I'm trying. Trying to do."
Windy sighed. "Well...ok. See you later, dear. Good luck!" She spread her wings and flew away.
"Whew!" Rainbow said. "That was a close one. So...maybe that mare over there."
Fluttershy shook her head. "If you're the most handsome pony in Equestria, you should be able to attract ANYPONY. Anypony at all."
"So what do you want me to do?"
"First of all...instead of YOU picking the pony, we should make it more of a challenge. I'll pick a pony randomly. And also...it should be like when you clear the sky for a special event. Give it a time limit."
Rainbow's mouth fell open. "You want me to attract somepony in ten seconds flat?" He scuffed the grass again. "Um...sure! I can do that. No problem!"
Fluttershy pursed her lips, looking up at the sky as she thought. "So that's easy, huh? Anypony who's just lucky can LOOK handsome, but this should be a game of SKILL too. So...come with me."
She led Dasher out of the park, and down the street.
***
"Go into that building," Fluttershy said, "and in ten seconds flat..."
"Yeah?"
"Of the ponies sitting at the bar, pick the third pony from the left...and in ten seconds flat, break her or his heart."
"That's ridiculous!" Dasher said. "Nopony can do that! Nopony should even TRY to do something like that!"
Fluttershy nodded. She said quietly, "That's what I thought. I THOUGHT you were just bragging." She sighed. "But since I know it's very hard...I'll give you a whole minute. SIXTY seconds." She sighed. "If you think you even have a chance."
"Oh yeah?" Dasher said. "I'll DO It. Just to prove you wrong. I'm the best there's ever been, and I'll DO it!"
Dasher strode up to the door, shoved it open, and stomped into the bar.
"You there!" Rainbow said. "You! Yes, you!" He put a forehoof on the shoulder of one of the ponies facing the bar. "Blondie, you with the do!"
The light green pony turned around. "Huh?"
"Let's go on a date! You, me, right now!"
The stubbly-faced stallion blinked. "Um...?" He blinked again. "Where do you want to go on the date?"
"Right here should do." Dasher leaned forward, grabbed the stallion in both forelegs, and shoved his lips against 'Blondie's.' "Aren't I a good kisser? Aren't I? Aren't I the BEST KISSER IN EQUESTRIA?"
The stallion swallowed. "I don't know."
"How dare you say I'm not the best?" Dasher tackled 'Blondie,' and kissed him more vigorously, mashing his lips all over the other stallion's face.
"So, Zephyr...do you love me?" Dasher grinned.
"Dash, you know I've always found you attractive. Ever since you and I were--"
"Well, too bad!" Dasher said. "You and I are OVER."
"But...we're a couple? I didn't even know were were a couple."
"NOT ANYMORE!" Dasher said, shoving the other stallion's chest and walking away.
"No!" Zephyr said. "Give me another chance!"
"Too late!" Dasher called out over his shoulder. "You should have appreciated me while you had me."
"Nooo!" Zephyr wailed, but Dasher was already gone.
***
The next day, inside the same building, Zephyr counted out bits and shoved them across the bartop at Fluttershy. "You win the bet, sis. I don't know how you did it, but you DID convince Rainbow to kiss me right on the lips. And let me tell you...this was the best bet I've ever lost."