Scootaloo's Best Sleepover Ever

by Matt11


One Fan to Another

Scootaloo started tossing and turning in bed, trying in vain to go to sleep. Why was she having so much trouble? She’d never had this kind of problem before. She was sleeping over at Rainbow Dash’s childhood house, with Windy Whistles of all ponies too.

So how come she wasn’t able to get to sleep? She was tired and wanted to rest, but it seemed like her body was conspiring against her.

The filly reluctantly rose from the bed she was sleeping in. Maybe it was just the unfamiliarity of the room she was in? Or maybe she was just feeling lonely? Either way, Scootaloo decided she would have no choice but to bother Windy. “I hope she doesn’t mind. It’s only for this night.” She thought to herself.

Windy was quite surprised to have her bedroom door opened and for Scootaloo to come trotting in. “What’s the matter, Scootaloo?” Windy asked as she sat up in her bed and turned on the light. “Did you have a bad dream?”

Scootaloo shook her head. “No,” Then she sighed and blushed. “I… can’t seem to fall asleep and… well…” She trailed off, too ashamed to complete her sentence.

Fortunately for Scootaloo, Windy quickly picked up on what her charge was trying to tell her. “Oh, I see. You want to sleep with me for tonight, is that it?”

“Y-yeah,” Scootaloo reluctantly admitted. “Would that… be okay with you? I don’t want to be a bother.”

Now it was Windy’s turn to shake her head. “I’m sorry, my little pony. But you’re too old to be sleeping with someone else,” She got up from her bed and scooped up the filly, carrying her back to Rainbow Dash’s bedroom and depositing her gently on the bed again. “Maybe you’d like me to sing you a lullaby? Or I could fix you a glass of warm milk, that always worked with Rainbow Dash whenever she couldn’t sleep.”

Scootaloo yawned again, this time more audibly. “I don’t really care, but… sometimes when I was younger and couldn’t sleep… I think my mom would sing to me. I don’t remember what she sang though.”

The older pegasus just smiled. “Well if you hum a few bars, I can try to sing it. I remember all the best songs for helping young ones nod off.”

The pegasus filly obliged the request and started humming a little. But she found herself growing drowsy before Windy could even sing a single verse. She finally dozed off just as Windy started to sing.

Windy smiled and kissed her charge on the forehead. “She’s so much like my little Dashie when she was younger. And just as adorable too.” She thought.


The next morning, Scootaloo awoke feeling strangely refreshed. That was the best night’s sleep she’d had since she couldn’t remember when. As she went about her morning hygiene routine, she thought briefly about how motherly Windy Whistles had been to her already. It was kind of like the mare was Scootaloo’s true mother.

At that the filly blinked. That wasn’t right. Windy Whistles could never take Dizzy Twister’s place and Scootaloo never wanted that to happen. Much as she might wish her mom could be around as often as Windy was, she’d never want to trade!

Well the tomboyish pegasus quickly forgot all about that little thought, more important matters quickly occupied her mind. Namely breakfast.

Breakfast was a relatively uneventful for Scootaloo, Windy prepared her a bowl of oatmeal complete with honey and strawberries, and the filly downed it in a matter of minutes.

Following that hearty meal, the filly opted to again play some board games with Windy. Only find out once again that Windy was a tough opponent to defeat and one that never went down easily.

“Don’t feel bad, Scootaloo,” Windy consoled the filly after the final game ended in a victory for her. “Even my husband has trouble beating me games, except when I let him win of course.”

“For the record, you weren’t doing with me in any of the games I beat you in. Or were you?” Scootaloo questioned. “I always hate it when ponies lose just to make me feel better.”

Windy chuckled. “I most certainly didn’t intentionally lose, Scootaloo. I was playing to win, as I’m sure you were.”

“You bet I was!” Scootaloo boasted as she buzzed her wings. “You’re the only fourth pony I’ve ever lost more than I’ve won against! The other three being my Auntie Lofty, Rainbow Dash, and Diamond’s mother,” She shuddered and shivered. “I don’t know why, but even now she still gives me the creeps. I don’t know what Filthy Rich sees in her.”

The elder pegasus just nodded. “Spoiled does have quite the reputation about her, but it’s not my place to judge her or second guess her husband’s choice in marriage. She doesn’t do anything bad to you, does she?”

“Nah, mostly she just pretends not to notice me. Except for a few times I’ve maybe ‘accidentally on purpose’ showered her with dirt while riding my scooter,” The tomboyish filly giggled. “But is it wrong if I say it serves her right for being a not very nice pony?”

Windy gave a wink. “Your ‘secret’ or whatever you wanna call it is is safe with me. I don’t think it’s entirely wrong of you to think that. But I always try to see the good in everypony, regardless of what they may be like,” Then she decided to change the subject. “Now how’s about we look through some more family photos? You saw a lot of Rainbow Dash’s baby pictures, but don’t think for a second she stopped being adorable when she became a filly or a young mare.”


The next hour or so was spent with both pegasi on the couch, browsing through the Dash family album. There were still a few baby pictures of Rainbow Dash to sort through (including one with her wearing a diaper like a hat), but the focus mostly went to her filly years.

One in particular caught Scootaloo’s eyes. It was of an excited looking Rainbow Dash standing next to her parents, as they posed together outside the Cloudsdale Stadium with a much younger looking Wind Ryder.

“This was the first Wonderbolts show we ever took Rainbow Dash to,” Windy explained to the filly. “It was for Wind Ryder’s retirement. And coincidentally, it was the day he set that speed record that no Wonderbolt was ever able to beat.”

“Until he tried to get Rainbow Dash kicked out of the Wonderbolts,” Scootaloo protested. “I didn’t hear much, but Rainbow told me wasn’t a very nice pony when she finally met him. And Spitfire kicked him out for it.”

Windy could only shake her head. “What a shame. I never got the impression that Wind Ryder of all ponies would play dirty. He seemed like such a nice stallion and a fine captain in his day. He was even retiring despite the fact that he had several years left in him as a flyer, said he wanted to be with his grandfoals. Oh well, at least Spitfire’s done a good job of maintaining integrity in the Wonderbolts, especially now that Dashie’s one of ‘em. Wouldn’t surprise me if she ends up becoming captain in her own right someday, it was always her lifelong dream.”

“You really think I might be a Wonderbolt someday, even unofficially?” Scootaloo wondered as she looked at her wings. “They all say there’s plenty of non-flying positions within the Wonderbolts, but I’ve never heard of ‘em or seen ‘em.”

Windy gave a reassuring nod. “I’m sure that even if there’s not a position yet, Rainbow Dash will make one just for you. I know she’d want her number one fan by her side.”

“Yeah, so long as I don’t go joining rival stunt groups just to feel like I belong,” Scootaloo glumly commented. “I still can’t believe Rainbow forgave me for all of that. She was only trying to keep me from doing something dangerous, and all I could think about was myself.”

“Hey now, there’s no need to get so upset,” Windy protested. “You made an honest mistake and you regret it. Besides, you think you’re the only one who went through a rebellious phase in their youth? Because if so, you should’ve seen what Rainbow Dash’s phase was like. Bow and I didn’t think she’d ever come out of it!” And with that she turned the page, depicting what appeared to be a teenaged Rainbow with her mane and tail styled into a punk like attire. She wore a midnight blue boarding on black collar jacket, and appeared to have a small star on the right side of her phase.

“Whoa! Rainbow was into punk rock as a teenager?!” Scootaloo exclaimed as her eyes grew wide, this was the first she’d ever heard of such a thing.

“Unfortunately it was true,” Windy explained in a noticeably less than cheerful tone of voice, her expression even seemed to morph into a frown. “Don’t even know where she got it from, nopony in my family or Bow’s family ever went through it. One day, out of the blue, she just attended a punk concert and for two years it was all she could ever think about. If it wasn’t the Wonderbolts, it was punk rock. But after she grew out of it she got rid of all her clothes and equipment, and insisted on stealing every photo she could find of her during the phase. This was the only one that survived.”


When Windy finally closed the family photo album, the clock struck the hour. Twelve chimes signaled that it was noon, prime lunch time.

As if on cue, Scootaloo’s stomach began to rumble ever so slightly. “What’s for lunch?” She asked Windy.

The elder pegasus mare’s response took her charge by surprise. “I was thinking we could go to Sugarcube Corner and get some milkshakes. After all, it’s a lovely day. The pegasi must be working extra hard at the factory.”

“You think maybe my mom’s on lunch break right now?” Scootaloo asked. “Maybe we could go see her?”

But Windy shook her head. “Even if she is on lunch break she’s probably very busy. I know Bow sometimes had to eat lunch inside the factory so he could get back to work sooner, especially if he was working a double shift. Which he and your parents probably are.”

“Well, if we see her, can we still wave to her?” The tomboyish filly asked. “I… kinda miss her, and I’m sure she misses me too.”

Windy nodded. “We’ll keep a lookout for her, my little pony. Now come on, it’s quite a walk to Sugarcube Corner from here.”


Unfortunately for Scootaloo, despite the trip to and from Sugarcube Corner, she and Windy didn’t see Dizzy Twister at all. A fact that left the filly feeling just a little bit downtrodden when they returned to Rainbow’s childhood home about an hour later.

But Windy knew just how to cheer up a down in the dumps filly, a few friendly rounds of hide n’ go seek in the backyard.

Scootaloo proved to be a lot better at this game than any other, she found hiding places that took Windy forever to consider and had no trouble finding Windy when it was her turn.

That night, Windy surprised Scootaloo with an invitation to a pillow fight. As she put it, it was a way for the filly to let out excess energy so she’d sleep better (and reduce the risk of her rolling out of bed).

“You’re going down! My mom’s a pillow fighting champion, and she taught me all the best tricks of the trade!” Scootaloo boasted as she grabbed a pillow and chased Windy around the bedroom.

Windy just giggled. “I’m no stranger to pillow fights myself, Scootaloo. I took part in more than my fair share when Dashie was growing up.”

“And I’ll bet she whooped your sorry rump every time too!” Scootaloo declared.

“Only way to find out is if you can catch me!” Windy teased as she continued to run around the room, taking great care not to bump into anything.

Ultimately, Scootaloo managed to catch Windy off guard and hit her over the head a few times with the pillow before Windy decided the pillow fight was over.

Just as Windy had hoped, the fight had worn Scootaloo weary. She was already sound asleep by the time she was deposited on the bed. And Windy couldn’t help but think the filly looked oh so adorable in this state, like a little angel. “It’s funny. I never imagined I’d ever have another foal after Rainbow Dash was born. And yet ever since Scootaloo came into my life, it’s like she was that second child,” She thought to herself. “I’m so glad Dizzy isn’t jealous of the fact that her daughter likes to spend so much time with my husband and I. I could never be the mare she was, she’s not quite as easy going as I am. And definitely not a super fan.


The rest of the weekend passed by in the blink of an eye and sooner than either pegasus would’ve liked it was Monday morning. That meant school for Scootaloo.

Even as the filly was packing up her things and getting ready, Windy could tell her charge was… distracted for lack of a better term. She had a pretty good feeling why that was too. “Scootaloo, is something the matter?” She inquired in her cheerful tone, trying to make it sound like she suspected nothing. The last thing she wanted was to make Scootaloo feel like she was being put on the spot.

Scootaloo heistated for a moment and her lips quivered, as if she were trying to stop herself from crying. Then she confessed. “This sleepover’s been great, Windy. Really great. It’s just… the way you talk, the way you’re always so concerned about me. It’s like your mother. Not my actual mother, but like a second mother if you know what I mean.”

Windy nodded. “I most certainly do, and I don’t see what’s wrong with that. I’m proud to consider you part of my family, especially since you and Rainbow Dash are honorary big sisters.”

But the tomboyish filly protested. “That’s the thing though. I don’t like the idea of seeing you as a second mother, or even a third mother if I count Aunt Holiday and Auntie Lofty. I don’t like the idea that I project what I want in a mother onto you. I love my mother! She’s, well, my mother! It just doesn’t feel right to see anypony else in the same light, but at the same time it feels natural! Especially when you do stuff like this with the sleepover, and helping me when I can’t go to sleep.”

Windy just lightly stroked the filly’s mane and did her best to calm her down. “Scootaloo, you can have more than one pony you consider a mother. I certainly don’t want you to feel like I’m trying to replace your mother, or that anything I’ve been doing is because I want you to consider me your mother. If I’ve been putting any kind of pressure on you at all this weekend, I’m sorry. The whole reason I wanted to have this sleepover, was so that I wouldn’t be all by myself while my husband was working. And when Dizzy approached me with her problem about having to go into work as well, I saw an opportunity for the both of us to solve our problems.”

“So then, it’s totally okay if I consider you like a second mom to me, right?” Scootaloo asked as she looked at the mare. “I can still love my mom and love you, right?”

Windy firmly nodded and smiled. “Of course, Scootaloo. Nopony ever said you had to choose between one or the other.”

Huh, now I know how Terramar must’ve felt when Apple Bloom, Sweetie Belle, and I were trying to help him figure out where to live.” Scootaloo thought, realizing she still kind of owed the hippogriff/seapony an apology for arguing and fighting with Sweetie Belle instead of trying to solve his problem.

“Now come on, no time for long faces,” Windy spoke up as she reluctantly ended the embrace. “School will be starting soon and I promised Dizzy I’d make sure you got to class on time. That’s a promise I intend to keep.”

“Wait, before I go, there’s something I need to do!” Scootaloo interrupted. She quickly dug into her saddle bag and pulled out a camera. “I actually kind of forgot I had this, good thing I remembered now!” She declared and snapped a picture as she stood in front of Windy. She then gave the photo to the elder pegasus. “There, now you’ll have something to remember this weekend by.”

“Oh Scootaloo, it’s perfect!” Windy happily exclaimed. “This’ll make a fine addition to the family photo album! I’ll make sure to cherish it forever and ever!” She set the photo down carefully on the kitchen table, and then she and Scootaloo set off for the Ponyville schoolhouse. Both already looking forward to the next occasion when they would be together.