All things considered, Big Macintosh and Cheerilee’s relationship ended on rather amicable terms. They were no less friendly to one another than they had been beforehoof; in fact, if anything, they were friendlier still. Cheerilee made a point to see her ex-coltfriend once or twice a week when she came to town shopping for apples, and their conversation was always pleasant and never awkward. The two still met from time to time over coffee to talk about school business, farm business, or no business at all – just casual, friendly chatter. But friendly chatter was all it was. They had come to see that there was nothing more between them than a simple, happy friendship, and they were both content to leave it as such.
Their friends, they were pleased to discover, shared in their contentment. Those closest to them just wanted them to be happy, and if they were truly happier as just friends then that was fine by them. Not everypony was quite as thrilled about the situation, though – there were quite a few stallions who had hoped for a messy breakup, so that they could swoop in and rescue a heartbroken Cheerilee from the throes of despair. But aside from a few resentful suitors, things seemed to be going very well for the happy new ex-couple, and it didn’t take long for what little stir their breakup had caused to die quietly down.
Within a few days, Big Macintosh had settled back into his old routine as though his romance with Cheerilee had never occurred. He actually found work on the farm a little easier without all the concerns of a relationship cluttering his thoughts. “It’s kinda nice, really,” he would always answer when asked about the breakup. “Took a little while to get back in the swing of things, but it really ain’t bad bein’ single. Just gives me more time to focus on the farm, and on my family.” And he meant it, too – Big Mac was truly a family stallion, and his granny and sisters would always be first in his heart, the way he figured.
So it was that on a calm, breezy afternoon in mid-spring he found himself returning to the old grind with ease. He moved from tree to tree, knocking down bucketfuls of apples with each kick, his mind clear of all diversions and totally immersed in his task. He was so focused on his work that he never once realized that he was being watched.
Fluttershy stood sheltered in the shadows of a particularly large apple tree. She was quite some distance away from the red earth pony – far enough that he wasn’t likely to notice her, unless he was actively looking for her. But she could see him well enough. For almost a full minute she stood and watched him as he worked, keeping as still as possible so as not to catch his attention.
Soon he passed out of sight, moving on to another part of the orchard, having gathered all the apples he could from this area. The second he left, Fluttershy slumped against the nearest apple tree and hung her head, blushing furiously.
She felt pathetic. Spying on Big Macintosh while he worked – what foalish behavior! And yet here she was, chasing after her longtime crush like a little schoolfilly. She took several slow, measured breaths and made a concerted effort to relax. It didn’t work: her heart still raced, her stomach still fluttered, her blush deepened. So she tried talking to herself.
“Oh, what am I going to say to him?” she said aloud, albeit very softly. “I…I suppose I could just ask him how he’s doing, and maybe that could lead to talking about Cheerilee…and maybe that could lead to my asking him if…if he…if I could…” she trailed off. She couldn’t bring herself to say it even when nopony was listening. Pathetic indeed.
A pair of pink saddlebags rested against the tree at Fluttershy’s side. She reached into one of them and produced a book: her diary, which she had lately taken to carrying with her at all times. Thoughts seemed to spring into her mind quite often these days, thoughts she wanted desperately to share with someone; but she was still far too shy to discuss her secret with anypony, even her best friends. Her dear diary would have to do for the time being.
Taking a pen in her mouth, she flipped through the book to the first blank page and began to write:
It has been one week since you-know-who and you-know-who-else broke up. I was going to talk to him yesterday, but…oh, I just couldn’t! It seemed too soon. Do you think it’s still too soon? Maybe I should wait another day….
Oh, what does it matter, anyway? I could wait for months and I still wouldn’t know what to say to him. I’ve never dated anypony before and I don’t know how to ask someone out. It all just seems so hopeless….
I’ve started thinking about talking to someone – other than you, I mean. Of course, I’m always glad to talk to you, but sometimes I just wish I had someone else. I really, really don’t mean to hurt your feelings, Diary, but it would be nice to talk with somepony who really listens to me. I don’t mean to say that you aren’t a good listener, it’s just that…oh, dear. Never mind.
Fluttershy spat the pen from her mouth and looked back over what she had written. The way her mind tended to wander when she wrote, she often found herself saying things to her diary that she hadn’t known she was thinking. Now was such a time. Was she really ready to talk to somepony about her crush? Her face darkened in contemplation.
No. No, she just couldn’t. Maybe, eventually, someday, she could spill her heart to a close friend – Rarity, probably, or Twilight, or maybe even Applejack – but not yet. After all, she’d only been in love with Big Mac for…how long, now?
That thought gave her pause. Just how long had it been since that awful Hearts and Hooves Day? It didn’t feel like very long, but Fluttershy couldn’t be sure. Time, as she perceived it, had melted into an emotional blur, each day nearly indistinguishable from the previous; and all of them were spent pining and longing and trying to fill her empty heart with idle distractions. The date often went neglected in favor of more pressing concerns. She hadn’t even bothered to date most of her diary entries; it just didn’t seem important to her.
Curiosity took hold of her and she flipped back through the pages. At length she came across the entry she’d been searching for:
I know we haven’t spoken in a very long time, but this is kind of a special occasion and I just wanted someone to talk to. I’d try talking to my friends, but…I just can’t. I wouldn’t know how to say it. It would be so embarrassing. But I know I can always talk to you. You won’t laugh at me or make fun of me.
Tomorrow is Hearts and Hooves Day. Every year since I came to Ponyville, I’ve spent Hearts and Hooves Day at home by myself. Well…not really by myself. I have Angel Bunny, of course, and sometimes my friends stop by to visit me, but it’s not the same as having a special somepony to spend the day with. I’m not really lonely, I don’t think…well, maybe just a little. But I know what I can do to change that.
I’m going to ask Big Macintosh if he would like to be my special somepony, if only for the holiday. He’s so kind and sweet, and it would mean a lot to me if he said yes. I’ve been thinking about him a lot recently – do you…do you think that means I’m…I’m…that he…that I….
The writing after that point grew quite shaky and nigh-illegible. Fluttershy smiled in reminiscence. She remembered just how she had felt when she wrote that entry: uncertain, frightened, and more than a little excited. Indeed, it was the first time in her life she could remember feeling scared and actually liking it; it was a good kind of scared, the kind that told her that something new and amazing was about to happen.
Her face fell. “But it didn’t happen,” she said softly to herself, remembering what had happened next. She turned to the next entry:
Today is the day. Today is the day. If I just keep telling myself that, I’m sure I can do it. Today is the day.
I have a plan, sort of. I’m just going to go to Sweet Apple Acres, find Big Macintosh, and…tell him something. I don’t know what I’m going to say yet. But I’ve decided that I have to say something. Maybe I’ll just come right out and ask him to…if he would like…well, you know. Oh dear, I hope I’ll be able to say it when I actually see him. If I can’t even say it to you, Diary, how will I ever be able to say it to Big Macintosh? I’m really worried….
No. I can’t let anything stop me. Today is the day. Today is the day. Today is the day.
Her eyes brimmed with tears as she flipped over to the next day’s entry:
Yesterday wasn’t the day. And neither is today. And tomorrow won’t be the day either.
Big Macintosh already found a special somepony. It’s Cheerilee. Not me. Not Fluttershy.
I’m really happy for him. They seem happy together. Cheerilee is so nice. I’m sure things will work out wonderfully for them.
I…I just wish that I…that I….
The entry ended there; Fluttershy hadn’t been able to bring herself to write anything more. A few tearstains dotted the page.
After that point, the entries were all more or less the same: broken, unfinished musings and sad secrets. She could hardly bear to read them again. As she counted through the daily entries, it struck her just how long it had been since that dreadful holiday. Two full months had passed between Hearts and Hooves Day and the previous week, when Big Mac and Cheerilee had broken up. It was almost staggering how much time she had let slip down the drain, wallowing in her solitary depression.
Fortunately, the entries grew much less gloomy after that. Fluttershy had felt terribly conflicted when she’d first heard about the breakup: part of her was sad for him that his relationship hadn’t worked out; another part was happy that she now had a chance with him; and still a third part felt guilty about the second part feeling happy. Eventually, she had decided to ignore her guilt and take a chance while she still had one…which is how she ended up here, spying shamelessly on Big Macintosh and unable to bring herself to talk to him. Again: pathetic.
The sound of hooves striking a trunk echoed across the orchard, jarring Fluttershy from her memories. She perked up; Big Mac hadn’t quite left the area yet! She could still catch him if she tried. It didn’t matter what had happened in the past two months – today could still be the day! Mustering every last ounce of confidence her soul had to offer, Fluttershy rose to her hooves and –
A sudden loud yawn from somewhere overhead prompted the already-tense pegasus to release a nervous squeak and tense up even further. She dropped to her knees and trembled, eyes squeezed shut in terror. Had she been found out? Had Big Macintosh seen her? Oh, how embarrassing….
“Oh, hey Fluttershy! You okay down there?”
That voice – it wasn’t Big Mac. Fluttershy timidly raised her eyes. A cyan-coated, rainbow-maned pegasus was sitting in the tree, on a large branch just above her head. A pillow was situated against the trunk; she must have been napping.
“Oh…h-h-hi, Rainbow Dash,” Fluttershy replied. She stood up, embarrassed to have been so spooked by nothing. She took a deep breath and composed herself as best she could. “Yes, I’m just fine.”
“Really? You seem kinda nervous.” Rainbow glided down from the tree and landed at her friend’s side. “More than usual, I mean. What’s up?”
“Oh, it’s…it’s nothing. It’s just I, uh…I….”
“Hey, what’s that?” Rainbow interrupted. Something behind Fluttershy had caught her eye, and she walked around her for a better look.
Fluttershy turned around to see what had gotten Rainbow’s attention. At once her eyes widened in stark terror – she had left her diary lying on the ground, and open to today’s entry, no less!
“Oh, it’s nothing!” she said, frantically scrambling to block her friend’s view of the book. Fluttershy trusted Rainbow with her life, but not with her darkest secrets.
Rainbow tried to nudge her way around the other pegasus. “No really, what is it? Lemme see.”
“It’s nothing, really!” Fluttershy moved back and forth in a desperate attempt to keep Rainbow at bay. “I mean, it’s nothing that…I mean, you shouldn’t…I, uh….”
At last the cyan pegasus caught a good glimpse of the book. “Is that…is that your diary?” she asked.
Fluttershy nodded sadly.
“Aw, c’mon, Fluttershy! You can trust me. I’m not gonna go blabbing your secrets all over Ponyville. What don’t you want me to know?”
“It’s really, really nothing, Rainbow! I just…it’s….”
As if on cue, another loud knock came echoing from across the fields as Big Macintosh bucked another tree. The sound broke Fluttershy’s train of thought and brought a blush to her face once again. She tried to hide behind her mane, but it was too late – Dash had seen it.
Rainbow looked in the direction from whence the sound had come: she could see Big Macintosh bucking apples on a hilltop some distance away. The gears in her mind whirred as she glanced back and forth between the stallion, her friend, and the open diary; and then all at once it struck her what was going on.
She grinned. Actually, it was really more of a smirk. Whatever it was, she directed it right at Fluttershy and it made the yellow pegasus feel very uncomfortable. “Oh ho, Fluttershy,” said Rainbow, still smirking. “Hoping to catch Big Macintosh on the rebound, huh?”
“No! I mean, well…yes, but…I…I mean…oh dear oh dear oh dear….” Fluttershy turned aside, her face totally obscured by her long pink mane. This was almost as bad as being found out by Big Mac himself.
Rainbow’s smile softened just a tad. “Hey, don’t worry about it,” she assured her nervous friend. The cyan pegasus spread her wings, preparing to take off in Big Mac’s direction. “Just let me handle this. I’ll have you two hooked up in ten seconds fla – ”
“Oh no! No, you can’t!” Fluttershy interrupted, moving to block Rainbow’s flight path.
“What? Why not?”
“I need to talk to him myself,” she replied. “I’ve been waiting so long, I can’t just let somepony else do it for me.”
“Fair enough,” Dash agreed. “Then what’s stopping you?”
“I, um….” Fluttershy looked sadly at the ground. “I don’t know how to. I’ve never dated anypony before…what am I supposed to say to him? What do I do?”
“That’s your problem?” Rainbow nearly laughed. “Hay, that’s the easy part! Anypony can do it. Here, I’ll show you.”
Rainbow began to walk around Fluttershy in a slow circle. Her face bore an uncomfortably alluring expression, eyes half-closed and her mouth curled into a somewhat mischievous grin. “It’s all about how you look at him,” she said with a wink as she walked in front of her friend. Her rainbow-hued tail brushed Fluttershy’s muzzle as she passed. The yellow pegasus’s face turned beet-red. This wasn’t what she meant at all.
“And then,” continued Rainbow, “you say something totally clever. Like, ‘Hey, big fella. Wanna come back to my place and buck my apple tree?’”
“Rainbow!” Fluttershy cried. Her cheeks burned so fiercely she was afraid they might catch fire. “T-that wasn’t what…I didn’t mean…I’m not trying to….”
“Hey, calm down, ‘Shy. I was just kidding. I know you better than that.”
“Oh,” said Fluttershy, immensely relieved. “So…um…what am I really supposed to do?”
Dash shrugged. “I dunno. Mushy stuff like this isn’t really my area. I bet Rarity’d have some better advice for you – you know how into gooshy romance she is.”
That sounded like a good idea to Fluttershy, and she nodded. Rarity was one of closest friends. If there was anypony she’d be willing to spill her secret to, it’d be her. “Thanks, Rainbow. I’ll talk to Rarity as soon as I can.”
“Great! Sounds like a plan,” her friend answered. Another loud buck sounded across the orchard. The rainbow-maned pegasus spread her wings and took to the air. “Now, if you’ll excuse me, I’ve got some Zs to catch. It’s getting kinda noisy around here.”
She flew off at high speed in a multicolored bolt, only to return a moment later and hover just over Fluttershy’s head.
“Hey, ‘Shy,” she said, a little more softly than usual. “Just wanted to say this before I forgot: I’m really proud of you.”
“You’re…proud of me? What for?”
“For actually insisting on talking to Big Macintosh yourself. You remember how shy you used to be? This time last year, if you’d had a crush on Big Mac, you would’ve just holed up in your cottage and let somepony else to do all the talking for you.”
“But…but I haven’t talked to him yet. I’m still not even sure if I can.”
“But you want to, don’t you?” Rainbow asked, and Fluttershy nodded in response. “Then there you go. That’s initiative. You want to do things for yourself and you’re willing to try. That takes guts.”
Fluttershy looked back up at her friend, her eyes bright and her face beaming. “Thank you, Rainbow Dash. That means a lot to me, coming from you.”
“Heh. Don’t mention it,” Dash said with a grin, and took to the skies once again.
As the cyan pegasus shrank into the distance, Fluttershy turned and looked back in Big Mac’s direction. He had moved quite a way away by now, and was little more than a red shape on a distant hilltop. But somehow, Fluttershy felt closer to him than she ever had before. She finally felt like he was within her reach.
She finally felt like she had hope.