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Winning Him Over

by Trials

Chapter 1: The Competition

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Winning Him Over

“Here’s another batch, Mac!” the mare cried out from the foot of the hill. With a sigh, she wiped her brow. It was dampened by sweat, but she didn’t mind. It was hard work collecting apples, but she had to earn her keep somehow. Her eyes wandered over to the horizon. The sun was finally setting, sending forth a burst of several different shades of orange into the sky as it began to sink below a faraway hill. With a glance upwards, she could see the occasional glimmer of a distant star on the canvas of pure darkness. The mare gasped, simply taking in the beautiful view. Her mouth fell open.

“Nice haul,” said the voice of a stallion. Smarty Pants shut her mouth so quick, she heard her teeth click together. She turned to face Big Mac, who was busying himself with the basket of apples. Smarty would never admit it, but she hadn’t heard him approach. With a grunt, he placed the basket on his back, and began making his way back up the hill. “Okay, that’s enough work. Come up when ya want to,” he said, pointing to the house.

“It’s a nice view, isn’t it?” Smarty asked, turning back around to face it.

“Gets real pretty about this time,” Big Mac confirmed.

“Don’t you just want to sit here and watch the sun go down?” she tried.

Big Mac hesitated. “Can’t.” he said bluntly. “AJ wants me for somethin’.”

Smarty raised an eyebrow. “She always does,” she said softly.

“What?”

“Huh? Oh, nothing,” Smarty lied. “Just saying how gorgeous the horizon looks.”

“Certainly does,” Mac said before walking up the hill.

Smarty watched the stallion as he left. When he was over the curve of the hill, she sighed. She felt like sitting down. With a yawn, she leapt forward, falling softly on the ground. She bowed her head, smelling the rich scent of freshly-cut grass. Of course, Smarty was used to the smell by now. After living on an orchard for a few weeks, it was practically the only smell around the place, aside from the occasional scent of a delicious apple pie. Granny Smith was an expert with pies. That didn’t mean she didn’t enjoy the grassy smell, however; it reminded her of the fact she was alive.

She raised a hoof to her chin, balancing the weight of her head on it. With another sigh, she looked up into the sky again. There were more stars illuminating the darkness. It was beautiful, but she had other things on her mind.

Big Mac was having trouble seeing Smarty’s actual intentions. Ever since the night they had shared, he had been unfathomably difficult to speak to. Actually interacting with him was a completely different story. Smarty didn’t know if he was just oblivious to her feelings, or if he was doing in on purpose. Moreover, she didn’t know which one was worse.

Smarty knew that he wanted a friend, but that was it. Perhaps his definition of ‘friend’ was slightly different to hers. After all, it was quite a subjective term. Even then, with her... willpower, her determination, as it were, she was surprised he hadn’t realised. Especially after that night. He had been just as forward as she had been, but it simply disappeared the next morning. The promised conversation never happened, and they certainly didn't go into the same bed again. That could’ve been because of Applejack finding the pair of them cuddling in the same bed...

Maybe he was just ignoring her? It was still possible. With a body like his, it must be hard to avoid attention from the mares around town. The last time they walked through Ponyville, in silence, as she recalled, Smarty noticed they couldn't keep their eyes off of him. What if he had his eyes set on another—

Shut up. Smarty let her head fall to the grass. She just didn’t know. She bumped her head several times on the ground. Shut up, shut up, shut up. All she did know was the fact that she could keep trying. With a stretch of her tired legs, she got up from the grass. The last shade of orange had finally disappeared below the horizon, only to be replaced the dark violet of the night. While she did enjoy the peace of the night, it was starting to get cold. She began making her way up the hill, in the same hoofsteps Big Mac had made only moments ago.

Fortunately, the lights shone through the curtains of the house, allowing Smarty to see where she was going. It wasn’t as if she would smack into a tree without the light, but it put her mind at ease. That way, she could see any timberwolves sneaking up on her again. Still, she kept her head on a swivel. Just in case. Following the path of the hill, she eventually found herself on the doorstep of the house. Smarty didn’t like calling it her ‘home’. ‘Home’ sounded like she owned it, but the truth was: she was simply doing work in return for shelter and food. Of course, that wasn’t the way Applejack would put it—she would most likely say something kinder—but it was the truth.

“Jus’ hurry up, Mac,” said Applejack from behind the door. “Otherwise, it’ll get cold.” Smarty heard the twist of the handle, and Big Mac almost collided with her as he stepped down.

He blushed. “Sorry,” he mumbled, turning away.

“Can I come?” she asked.

“Oh. Uh. I dunno ‘bout th—”

“Sure!” Applejack interrupted. “Mac would jus’ love the company! Yer takin’ that pie to my friend, Rarity. Ya met her before, I think. It’s a bit late out, so don’t dilly-dally, okay?”

Smarty nodded eagerly. She tried to push the thought of Mac attempting to reject her to the back of her mind, but she knew it was going to be hard. With a fake smile, she began walking. “C’mon, Big Mac! Let’s go already!”

“Right behind ya,” he said as he placed the pie in his saddlebag.


It took longer than Smarty expected to reach Rarity’s boutique. Maybe it was because the time seemingly dragged on forever. After all, time flies when you’re having fun. Big Mac hadn’t spoken a word, and neither had she. Big Mac would occasionally catch her watching eyes, and she would always look away at the last moment, but that was all the interaction they’d shared. At least Smarty had the silence to think, even if each little thought was trying to emerge as the most important in an incoherent maelstrom of words, creating a distracting haze that occupied Smarty as she walked.

Hell, even recognising her thoughts as animate objects—rather than the electrochemical messages they truly were—engaged her mind.

Shut up. In complete silence, aside from the insane amount of noise in her mind, the pair of them made a left turn on the main street of Ponyville. The darkness shrouded the top of the boutique, but the lights inside thankfully illuminated the entrance. Without a word, Smarty walked over to rap on the wooden door. Big Mac exchanged a glance with her for the first time, but was interrupted as soon as her eyes latched onto his.

“Good evening!” Rarity said, smiling warmly as she indicated inside, “please, make yourselves at home!”

“Uh, it’s fine, Miss Rarity,” Big Mac began, “it’s quite late, and we’re mighty busy. Here’s the pie ya ordered,” he said, reaching into his saddlebag to pick up said palatable pastry. With a giggle, Rarity took it into her own hooves.

“Thank you very much, but you can’t stay out here. Nonsense!” Rarity exclaimed, laughing politely. She peered around the side of the door, exactly where Smarty was hiding. “Oh, Smarty Pants!” she cried, grabbing her by the hoof. “You didn’t say anything. It would be rude not to invite you in for a cup of tea, especially when it’s this cold!” she said, shivering for effect.

Smarty hesitated, but then nodded. “Nice to see you again, Rarity,” she said. Though I hope you won’t try to fit me into another one of those cursed dresses, she thought.

“And you!” Rarity said, grinning. “Tell me, what’s it like living on an orchard? I could never do it myself. Of course, I mean no offence, Big Mac,” she added quickly.

“It’s fine,” he said simply. “Livin’ on an orchard ain’t for everyone.”

“Quite,” she confirmed, allowing an awkward silence to fall between the three. Smarty only just realised that Rarity was waiting for an answer when she began talking again. “Anyway, come in! It’s been a while since we’ve caught up.”

“I’ll stay out here,” Big Mac said. “Wait for ya to finish.”

“Are you sure?” Rarity asked, pouting slightly. Big Mac nodded firmly. “Well, just you and I, Smarty Pants! We can have a proper mare talk...” Rarity rubbed her hooves together, giggling as she bowed her head.

“Uh, sure,” Smarty said. Rarity began walking inside, allowing Smarty to shoot Big Mac a worried glance before following the mare. Much to her dismay, he didn’t even notice. He was watching the starry sky above, which was obviously more important than herself. Obviously. With a silent sigh, Smarty entered the boutique and shut the door behind her. She would’ve said farewell to him, but she doubted he would even hear it through the thickness of his skull.

“Rarity?” she called.

“Over here, darling!” Rarity replied. Smarty followed the voice, going straight through the wide room she’d entered, and into the next room. Rarity was standing over the pie, her knife at the ready. “Would you like a slice while it’s still warm?” she asked, cutting away before waiting for the reply. Smarty’s stomach just so happened to grumble at precisely the wrong moment. “Oh, somehow, I think I know the answer!” Rarity exclaimed, laughing.

“No thanks, Rarity. Had enough apples in the past couple of weeks to last a lifetime,” Smarty admitted. She knew Rarity would rather force-feed her than let her go without food after hearing her stupid stomach.

Instead, Rarity simply paused. “Fair enough,” she admitted, “I think they are slightly... fanatical about apples over there, if you don’t mind me saying.”

Smarty’s eyes went wide. “I thought I was the only one!”

“No, of course not,” Rarity said. “Then again, it is a family tradition, so that’s neither here nor there...” The unicorn placed the slice of pie gently on a plate. As delicately as possible, she took a small bite out of it, shuddering as the overwhelming flavour tantalised her taste buds. “So...” she began, recovering from the rich taste, “is there... something between you and...” She tilted her head to the left.

Smarty cocked her head. “Excuse me?” she asked, making sure to remain polite.

Rarity beamed. “Oh, I think that little accent Applejack has is rubbing off on you. Rather interesting,” she said, giggling once more. Silence fell between them.

“What did you mean?” Smarty asked. Dodging questions wasn’t unfamiliar territory with Rarity, and she knew this from the first time she’d met her.

“Applejack’s accent? Oh, you must know. She often drawls her words. Says ‘yah’ instead of—”

“No, what did you mean?” Smarty asked. “About something between myself and...” She tilted her head in the same direction as Rarity had done.

Rarity raised an eyebrow. “Oh, come now. You don’t understand my meaning?”

“Hence why I asked,” Smarty said, growing irritated. She wouldn’t be able to hold her composure for much longer. It wasn’t like she disliked Rarity for dodging the question—even if it was rather disconcerting—but Smarty hated being made a fool of. She would much prefer being ignored to having her intelligence insulted, but Rarity was obviously opting for both.

“You. Him,” she said slowly. “There’s nothing between you two?”

“Him? Who are you tal—” Her mind finally made the link. Him. Big Mac and her. Her and Big Mac. Were it not for Rarity being in the same room, she would’ve verbally berated herself.

“Either that, or Big Mac was simply being the usual gentlecolt,” Rarity said. “Not every stallion will wait outside in the cold to walk you home.”

“Is that what it is?” Smarty asked.

Rarity shrugged. “As I said, it could be either.”

Smarty sighed. Rarity took another delicate bite of her pie. “Is it that obvious?” Smarty tried.

“Quite. I’ve seen the way you look at him," Rarity admitted.

“I thought I was keeping it quite subtle...” The unicorn let out a sudden laugh before apologising profusely. “Well, I don’t really feel like talking about it now,” Smarty complained, sulking.

“No, no, no, please!” Rarity begged, her voice desperate. “Take a seat! Make yourself at home!”

“I’m fine,” Smarty admitted. “The thing is, I don’t think Big Mac realises that I... like him. We shared this one night—”

“Oh, do continue!” Rarity exclaimed, smiling excitedly. Her eyes were twinkling.

Smarty’s brow furrowed. “No!” she cried. “It wasn’t anything like that. We just slept in the same bed for a night. It was... nice, but from that point onwards, Big Mac has barely said a word. It’s been a couple of weeks now, and the most interaction he’s given me is... well, the occasional statement. How lovely the weather is. How he’s happy with my work. Even then, it’s always me starting the conversations. I mean, what am I meant to do? I can read most ponies like a book, but it’s like Big Mac has a few pages stuck together! He’s as responsive as a rock, and that’s saying something! You can always roll a rock down a hill, or throw it somewhere! How am I meant to—”

Smarty felt a comforting hoof on her shoulder, interrupting her thoughts. She caught her breath, only then realising that she’d lost it. Rarity retrieved a handkerchief, gently dabbing Smarty’s forehead. Smarty hadn’t even noticed how hot the room suddenly was. “Thanks,” she said simply, going red from embarrassment. There she was again, looking like a moron. Nothing new there. Her head fell, and her shoulders slumped.

Rarity smiled cheerfully. “Not a problem, my dear. It’s obviously upsetting you. Now, a word to the wise: Big Mac isn’t exactly... big on words. He’s very shy. Why, I can barely get a word out of him myself. Sometimes, he simply feels that silence is better than words. As such, it can be rather difficult for him to present his feelings so willingly.”

“Oh, I’m beyond being subtle, Rarity,” Smarty admitted, nodding furiously. “If he doesn’t understand me, I have to be doing something wrong. The amount of times he's brushed me off... well, I don't know how many more times I can take."

“See, you are rather straightforward, much like me,” Rarity said. “We can both express ourselves to the world with ease, but it’s different for Big Mac. It’s not that he simply wants to mind his own business; I believe it’s physically difficult for him to show his feelings.”

Silence fell between the pair. “That’s stupid,” Smarty admitted.

Rarity shrugged. “A little.”

“Maybe it’s just because he doesn’t understand me? Maybe I'm doing something wrong?” Smarty asked, raising a hoof to her chin. “I mean, I could try to make it more obvious for him. He might just not... Oh, forget it,” she said. “Thanks for the chat, Rarity, but it’s getting late. Big Mac must be freezing outside. I’ll see you again.” Smarty began moving away. Fortunately, Rarity was occupied by chewing, so she couldn’t reply or keep her from walking away.

She could hear her desperately murmuring through the pie filling her mouth, but decided to keep walking. Smarty suddenly heard the sound of Rarity swallowing deeply, and then a sigh. “Wait!” Rarity cried. “I have an idea!”

“What is it?” Smarty asked, turning instantly on the spot.

“Why, aren’t you eager?” Rarity asked, giggling to herself.

“What is it?” Smarty repeated quickly, punctuating each syllable.

“We have something of a... tradition here in Ponyville. We are, as you can tell, very traditional around these parts. Every year, before the leaves on the trees fall to the ground, stallions who are not spoken for become involuntary participants of the Bachelor’s Buffet contest. Big Mac is among those poor souls, as tradition dictates.”

“Are you saying what I think you’re saying?”

Rarity blinked. “What would that be, dear?”

“I have to fight for Big Mac?” Smarty asked, her voice on the verge of cracking.

“Naturally,” Rarity said. “After all, it is a contest.”

“I can’t do that!” Smarty cried. “Competing with the cutthroat mares of this town? I’d have no chance!”

Rarity harrumphed. “I’ll choose to ignore that comment.”

“Oh, uh, no offence, of course,” Smarty said quickly. “Please continue.”

“As I was saying,” Rarity commented, clearing her throat, “it’s a contest to win the heart of the lucky stallion. It begins in a week or two, though I cannot remember the specific day, and goes on for a further week. You have a week to convince Big Mac into loving you, but there is a catch. As you said, other mares will also be competing for him. At the end of the week, Big Mac can either declare which mare he loves the most, or he can simply abstain.”

“Abstain?” Smarty asked, cocking her head. “Why would he do that?”

Rarity scoffed. “I don’t know. I even tried a couple of years ago, but he said what he says every year.”

“And what is that?”

“He’s waiting for the right one,” Rarity said, rolling her eyes. “A hopeless romantic, if you ask me.”

Smarty licked her lips. “Maybe I am the one.”

The unicorn let out a laugh. “Oh, believe me, that’s what every mare says when they opt for him! He’ll just end up lonely if he doesn’t settle down soon. Half the population of Ponyville have tried for him, and no such luck!”

“But I wasn’t part of that group,” Smarty tried.

“I don’t mean to put you off, I assure you,” Rarity said, “but I don’t want you to be hurt if the answer is... well, what I’m trying to say is—”

“It’s worth a shot,” Smarty finished.

Rarity hesitated. “It is,” she confirmed. The room became quiet once more.

“Well, I think Big Mac has been waiting for long enough,” Smarty said. “Thanks for your hospitality, and for the idea. It’s better than nothing.”

“Of course!” Rarity exclaimed, smiling again. “I’ll show you out.”

“Thanks, but no need. I can let myself out,” Smarty explained, beginning to walk away. “Oh, and Rarity?”

Rarity nodded. “Yes?”

“Could you... um, give me some advice when the time comes?” Smarty asked, her eyes pleading. “I’m not very experienced with talking and interacting with stallions, and—”

“Say no more,” Rarity interrupted. “Of course I can help you! I can teach you the proper etiquette of a mare, as well as... more obvious actions. Maybe a beautiful dress, hm? Some make-up? Easy to do, and it’ll certainly impress Big Mac.”

Smarty chuckled nervously. “That’d be great. Thanks, Rarity. Just something to give me an edge over the competitors, you know?”

“Well, as I said, there might not be many competitors,” Rarity admitted. “A lot of mares have already tried and failed with Big Mac, making them move onto other targets.”

“Just to be sure?” Smarty asked, raising an eyebrow.

“Of course!” Rarity exclaimed. “I’d be happy to. Whenever you need a word of advice, simply come to me. Now, that stallion is waiting in the cold for you, and I wouldn’t want you to start off poorly. Go, and just keep him happy,” Rarity said, pointing towards the door.

“Thanks, Rarity,” Smarty said. “I’ll talk to you soon.”

Smarty Pants continued her walk over to the door. With a heave, she yanked it open, leaving Rarity to talk to herself about the dress she had in mind for Smarty. She rolled her eyes. Smarty didn’t really like dressing up, but maybe it would help her win Big Mac’s heart. As she closed the door behind her, Big Mac glanced over. “Ready?” he asked. She looked him up and down, from his golden mane to his strong hooves and everything in between.

“Ready,” Smarty confirmed. Of course she was ready.

Author's Notes:

Damn, it feels good to write about Smarty Pants again.

Next Chapter: A Rival Estimated time remaining: 32 Minutes
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