The first thing to breach Cheerilee's senses is the faint sound of knocking. The second thing is an intense, throbbing pain in her head. The third thing is an unrelenting feeling of hopelessness.
She forces her eyes open, the crustiness on both them and her cheeks indicating that she had cried herself to sleep. The pain in her head will not go away, to the point where her vision is blurry even after she rubs at her eyes. She groans as she attempts to sit up, only to realize that she already is. As her vision slowly begins to clear, she reaches out in front of her and realizes that she fell asleep sitting at her kitchen table. Her hoof bumps into something, which promptly falls to the floor. The sound of shattering glass fills her house, and she winces as she realizes what happened.
She drank herself into a stupor last night before apparently passing out at the table.
She licks her dry lips and attempts to stretch her back, feeling a painful pop as she does so. A quick glance to the side reveals that she has knocked her ever-growing pile of unpaid bills onto the floor, along with the letters from Spoiled Rich. She must have done so in her drunken state last night, of which she remembers very little. She starts to crawl out of her chair, but she stops herself as she realizes that the floor is now covered in the broken glass shards of what was once a bottle of wine. A quick scan of the kitchen reveals that she drank almost three whole bottles of the stuff. It's a miracle she isn't in the ER.
Now having carefully lowered herself to the ground while avoiding the glass, she immediately walks over to a nearby closet where she retrieves a broom and dustpan. As she starts to clean up the glass, a sound catches her attention. There is someone knocking at her door.
...Well, that explains what woke her up. Also, this is perhaps the worst possible time for her to have a visitor. A nearby clock shows that it's almost ten. She's lucky that it's a Saturday, otherwise she would be in a whole lot of trouble.
Doing her best to finish cleaning up the glass as quickly as she can, she shoves the broom and dustpan back into the closet and makes her way to the door. However, just before reaching it, she freezes, choosing instead to grab the two other bottles of wine and hide them behind her fridge before answering the door. In the process, she gets a quick look at herself in the reflection of a small mirror she has on her fridge. She looks like an absolute wreck.
Hastily trying (and failing) to fix her mane, she finally opens the door.
"Mornin', Lee- WOAH! What happened to you?"
To her surprise, it's Anon, the man she spoke poorly of the evening prior under just a bit of pressure from Spoiled Rich. Which he heard.
"If I may steal your line, it's none of your business."
"Well... can't argue with that!"
Cheerilee narrows her tired eyes at Anon. He's dressed impeccably well. He tends to dress nicer than most thanks to Rarity's influence, but today he looks... well, to be frank, charming. The pink tie is a bit different for him, though. She didn't really think pink was his color, but what does she know about fashion?
However, as she looks closer, she notices something else. Dark circles are faintly gathering beneath his eyes. He has a bit of a slouch, too. If she had to guess, she'd say that he didn't get any sleep last night. On top of that, he carries a large, flat piece of what looks like black canvas in his arms.
"What are you doing here? It's not time for our lesson yet."
"I... huh?" Anon tilts his head at Cheerilee for a moment before his eyes open a bit wider, his expression indicating that he just realized something. "Oh! Oh my gosh, I cannot believe you forgot what today is."
"Is today something special?"
"Well, I was under the impression that it's going to be one of the most important nights of your life, but I mean, if you'd rather not go to the gala, I'm not making you~!"
Anon looks to the side with a cheeky smile. Cheerilee's ears droop and her eyes widen as his words finally register with her. Amongst everything that has been going on lately, she had completely forgotten.
Oh this is bad.
"I... I... I'm not ready! Oh sweet Celestia, I'm not ready!"
"Calm down, Lee. Our train doesn't leave for another couple of hours."
"Then why did you come over so early?"
"We'll just blame it on my intuition. I, er, figured something like this would happen."
"Something like what, exactly?"
"That you would be woefully unprepared for the gala."
"I would really love to argue with you, but I guess my words wouldn't carry much weight when I look like this."
"No, no they wouldn't. Now, what do you need to do to get ready?"
"Well, let me think." In truth, she has no idea. She is so unprepared for this that she's not sure how much she can do. She can't afford to get her mane done, she doesn't have time to doll herself up as she'd like... heck, she doesn't even own a formal dress. This is going to be a disaster, isn't it? "I need to fix my mane, I suppose. Grab my ticket... er..."
"You don't have a plan, do you?"
"You know me so well."
"Luckily for you, I was prepared for that too."
"I honestly don't know whether I should be flattered or offended."
"Both would be funny. Anyway, here."
Anon hands the flat whatever-it-is to Cheerilee, who only now notices that there is a zipper going down the center of it.
"What is it?"
She asks that question as she unzips it, but the answer makes itself known before Anon says a word. As it turns out, it's a bag for protecting formal clothing, and within that bag lies a jaw-droppingly gorgeous pink-and-green dress. She stares at the garment with wide eyes, unable to find the right words to convey what she's thinking.
"Rarity said she already had your measurements, so unless you've gained weight or something it should fit just fine."
"What a way to ruin the moment!" Cheerilee kicks Anon in the shin, but it isn't enough to hurt. He simply chuckles as he watches her eyes begin to grow misty. "This... Anon, I can't accept this."
"Sure you can. It's a gift. Besides, you're my date, aren't you? Plus, I got a matching tie!"
"S-since when am I your date?"
"Is that not implied by you being my plus one?"
"Aren't your friends bringing their friends and family? Those aren't dates!"
"Sure, but I'm bringing you. I suppose we could refer to it as a more casual sort of thing if you'd like, but that doesn't make my tie match your dress any less."
"Enough about the tie!" Cheerilee fights back tears as she cannot bear to look away from the dress in her hooves. Never in her entire life, even prior to Spoiled Rich's interference, could she ever afford something this nice. "How did you even get this?"
"I called in a favor from Rarity."
"How did you-"
"I did her taxes for her."
"W... what? How? You've only been in Equestria for a couple of months."
"So? Turns out, my degree was good for something. I just had to get the bit conversion rate lined up in my head and then it was all second nature."
"I..." Cheerilee cannot think of anything else to say. Instead, she throws herself at Anon, wrapping a hoof around his waist as best she can in the closest approximation to a hug she can manage given their height difference. "I guess I'll go put this on."
"Woah, hold on there. The dress is the last thing you need to put on."
"I'm sorry?" Anon reaches into his pocket and pulls out a small, silver ticket before handing it to her. "What is this?"
"A voucher to the spa. They'll get you all sorted out. Pretty sure Lotus can even do your mane for ya."
"I can't-"
"Shut up and go, Lee." She looks up at Anon, who gives her a knowing smile. "Gotta look your best when your dream is coming true, right?"
"But you... aren't you mad at me?"
"Hm? What for?"
"..." Did he not actually hear what happened yesterday? She wants to breathe a sigh of relief, but she'd feel bad if she did. Either he did hear what she said and he's playing dumb for her sake, or he didn't and she's hiding the fact that she talked smack about him behind his back. Either way, she's unsure of how to respond. "Never mind. Th-thank you, Anon. Truly. Nopony has ever done something like this for me before."
"There's a first for everything, right? Even an old mare like you needs some love." Before she can make a retort to his playful jab, he's already pulling her out the door. "Now come on, I know I said we have a couple of hours but we're still on the clock."
"Are you going to the spa, too?"
"Nah, I have some errands of my own to take care of. You enjoy yourself, okay?"
"R-right."
"We'll meet up at the train station before noon." Anon begins to walk away, but instead of his usual half-hearted wave goodbye, he turns around to face her as he walks backwards. "And don't forget your ticket! That would be a really predictable and avoidable problem!"
"Okay!"
Cheerilee is struggling to handle the whirlwind of emotions she's feeling at the moment. Her head hurts, she's tired, and her life may as well be crumbling around her. And yet, here she is, dress in hoof, about to get pampered at the spa and then taken to the gala of her dreams.
What else can she do but smile?
"Woah." Anon looks at Cheerilee with surprise as she approaches him at the train station. He wasn't kidding when he said the spa would get her sorted out. She got cleaned up, got a massage to wash away her fatigue, got her mane done, and she even got a hooficure. After that, she stopped by her house to try on the dress. Sure enough, it fits perfectly. She got a good look at herself in a mirror before she left, and the sight alone was enough to make her blush. The dress clings to her figure in all the right ways, and the color matches her coat and her eyes in a way that make both seem even more lovely than before. Never in her life has she ever felt so... "You look beautiful."
Yeah. That.
"I feel different, that's for sure."
"Got your ticket?"
"Right here."
Cheerilee shows Anon her ticket, which was tucked away in one of her dress pockets.
Yup. That's right. Her dress has pockets.
"Good. I already got our train tickets, so we're good to board."
He gives her a smile before taking a few steps towards the train and motioning for her to enter before him. She does, giving him a sly elbow before completely passing him by. With that, the two finally get on the train and make their way to their designated car. Along the way, they pass a few other ponies that are also dressed well. Not all of them are going to the gala, of course, but some most certainly are. And yet, each and every one has their eyes drawn to Cheerilee. There can be no mistake: She looks gorgeous.
Eventually, they make it to where they are supposed to be. There are a fair amount of ponies in this car as well, but they easily find their seats. Among the ponies sitting around them, Cheerilee recognizes several. Specifically, she recognizes Twilight Sparkle and her friends, who are right next to the pair.
"Hello, Anon! Hello, Ms. Cheerilee!" Twilight greets them with a smile. Her mane is done up as well, and she has a beautiful dress that compliments her features perfectly. And yet, it somehow still doesn't quite compare to Cheerilee's despite being made by the same pony. "Both of you look wonderful!"
"Thanks, Twi." Cheerilee glances at Anon. Seems like Twilight has reached that elusive nickname status he told her about. "You're all looking good, too."
"Well, Rarity did work really hard on our dresses."
"Speaking of!" Rarity, who sits next to Twilight, excitedly looks at Cheerilee with sparkles in her eyes. "I'm so happy to see that it fits you, darling. I must say, it was by far the greatest challenge I had to face going into this gala. But, after Anon told me about how excited you were, I knew I could give you nothing less than my absolute best work possible."
"G-goodness, I didn't realize it was so much of a hassle." Cheerilee blushes as she speaks.
"Not at all, darling! It was a very enjoyable challenge, and I am quite proud of the result."
"Thank you, Rarity. Really."
"You're very welcome! Ooo, I'm just so excited about tonight!"
After that, the group begins to converse about their expectations for the night to come. Twilight and her friends seem very adamant about tempering said expectations, and they advise Cheerilee to do the same. Granted, Cheerilee is older than them and feels like she has a better idea of what to expect, but hey, what does she know? Meanwhile, Anon stays quiet, silently grinning as his attention continues to be split between the group and the landscape outside the train's windows.
"Hey. Anon." Cheerilee keeps her voice low in an attempt to prevent the others from hearing her.
"Hm? What's up?"
"You're doing that thing you do when there's something on your mind."
"Am I?"
"Staring wistfully out the window while acting uncharacteristically quiet?"
"...Well, you got me there."
"Something on your mind?"
"I'm, er... I'm just not really looking forward to meeting with Celestia."
"Haven't you met her before?"
"Sure, but only briefly. Plus, Twilight did most of the talking for me. This is the first time I'll be around her for a prolonged period of time, and I'll be all on my own. Well, save for the untold amount of nobles that she plans to 'show me off' to."
"Princess Celestia is beloved for a reason, Anon. I don't think you have anything to worry about."
Anon hesitates for a moment as he stares out the window, his attention never directly geared towards Cheerilee.
"We'll see."
The two say nothing more as the train enters Canterlot. It gradually slows until coming to a complete stop at the train station, and the passengers are directed off of it one-by-one. Anon and Cheerilee walk side-by-side with bated breath as they slowly make their way across the grand city towards the castle that looms over all of Equestria. As they walk, Cheerilee notices how many looks the two of them are getting. Not only is she not the typical sort of high-class pony to attend an event like this, but Anon's human form sticks out like a sore thumb. The fact that he is essentially acting as her escort doesn't help matters. However, not even that can quell the growing excitement within her stomach as they slowly make their way across the small drawbridge and into the castle.
The Grand Galloping Gala has begun.