A Drinking Game
"One more bottle."
The bartender, an older stallion with a combed mane and well-maintained mustache, nods silently at Anon before reaching behind the bar and sliding him another bottle of whiskey. Anon digs into the sack of bits Twilight gave him and pays the modest price before taking the bottle with him to the back of the tavern. There is a small half-circle shape in the back wall where a large circular table rests, a well-padded booth built into said wall acting as the seating. This table provides a great deal of privacy, which Cheerilee can appreciate. Not that there's much need for said privacy, as the only other patron in the tavern is Berryshine, who is conveniently asleep at her table.
Cheerilee glares at Anon as he reaches the table. Her cheeks are a bit rosy, and although there is a bit of color to Anon's cheeks, it isn't quite as pronounced as Cheerilee's. There are three shot glasses at the table, only one of which is within reach of the tired teacher. Anon sits across from her, where the other two glasses are. An empty bottle of whiskey sits in the middle of the table, its contents having already been hastily consumed by the bickering pair.
"I couldn't tell ya the last time somepony bought me a drink."
"That's not surprising."
"Oh, shut up."
Cheerilee immediately reaches for the bottle, pours herself a shot, and throws it down effortlessly.
"I gotta say, I didn't take you for a drinker. You come here often?"
"No. I couldn't afford to if I wanted to."
"Ya know, you keep saying something to that effect, but I don't really get it. Twilight's paying you a lot to mentor me. I know teachers don't get paid much, but Ponyville isn't exactly an expensive place to live. What's up with that?"
Cheerilee smiles. It seems genuine, but there is a quiet sadness to her eyes when she does.
"No amount of liquor will get that out of me, so don't bother asking."
Anon puts his hands up innocently.
"Alright, fine. I didn't want to know about your stupid finances anyway."
"Peh. Well, what about you? Drink often? Looks like it, considering you've had twice as much as I have."
"I'm also twice your size, Lee."
"...Lee?"
"We're both off-duty right now, and I give my friends nicknames. Deal with it."
"Haha, what? You don't even have a job to be 'off-duty' from. And who says we're friends?!"
"You know as well as I do that I'm not referring to work. We're off-duty from our public images."
"I-"
"And yeah, I'd say you're the closest thing to a friend I've got in Equestria." Anon briefly widens his eyes as he is reminded of the day's events, immediately pouring two more shots in response. "Sounds like I'm gonna need more from now on."
Like Cheerilee, he downs both shots with ease.
"What about Twilight? Isn't she your friend?"
"Our relationship is... complicated."
"I've been wondering about that. What's the deal with you two? Why do you act so nice around her?"
Anon looks Cheerilee dead in the eyes. Neither are all that drunk yet, but they're both feeling a buzz, and they're both in the mood to act a bit more open than usual. This gives Anon an idea. He reaches for the bottle and pours another shot on Cheerilee's behalf before pouring two of his own.
"How about this? We take turns. You take a drink, you get to ask a question for the other to answer. If you refuse to answer or you fail to keep your drink down, you lose. You in?"
Cheerilee raises an eyebrow before an amused smile makes its way to her face.
"Sure. This day can't get any worse, so why not?"
Anon smiles right back at her, feeling a similar sentiment. He motions towards her glass, and she smiles and takes a shot.
"Well, to answer your first question, it's because she's the one that found me."
"That's all?"
"My... appearance over by the library wasn't exactly gentle. A bunch of magic was coursing through my body, essentially burning me alive from the inside out. Of course, I didn't know that at the time. I just knew I was dying. Then, in came a purple horse with bangs. Her little horn started to glow, and the next thing I knew, there was this light shooting out of my mouth and my body started cooling down. Then I passed out again."
"She saved your life?"
Anon nods.
"I have a personal policy to repay my debts, but that's not one I can ever truly repay fully. It'd be ridiculous to devote my life to her or whatever other movie trope you might be thinking of, so I do my best to give her as little trouble as possible."
"That simple, huh?"
"What were you expecting?"
"I guess I don't know."
Anon shrugs.
"Either way, you got your answer. My turn." Anon nonchalantly stretches, easily downing two shots before folding his arms behind his head and leaning back with a smirk. "If you're such a good teacher, why do you let those three fillies get bullied all the time?"
Cheerilee glares at Anon. He really went right for the jugular first, didn't he? Well, up yours, Anon. Two can play at that game.
"You know Diamond Tiara, the pink one?"
"Snooty little thing, that one."
"Yeah. Well, there's this mare that holds a powerful position on the school board named Spoiled Rich. For all intents and purposes, she is my boss. If I ever disobey a single thing she says, I'll lose my job. Guess who Diamond's mother is?"
Anon laughs boisterously, his voice echoing throughout the quiet tavern.
"That's how it goes, isn't it? There's always an authority figure pulling strings for personal gain."
"Not necessarily, but whatever. Anyway, it's my turn." Cheerilee has a devilish grin on her face as she prepares to ask her question. Once she has one, she takes her shot. "Who were you before you came to Equestria?"
Anon gives Cheerilee an amused, yet confused smile.
"I'm not refusing to answer here, but I do need to ask for clarification, Lee."
"What do I need to clarify?"
"That's a bit of an open-ended question, don't you think? Unless a philosophical debate is what you're going for."
She chuckles.
"Just give me a quick summary of your life. Sell yourself."
"Alright, fine." Anon cracks his neck - a nervous habit perhaps - as he prepares to answer the question. "Well, my name is Anon. I grew up in a town called Quinceton. Tiny place, population of maybe five hundred. I was an only child, and my mom died when I was still a baby. It was just me and my dad for a long time. Things were... rough, growing up. Don't get me wrong, my dad loved me with all of his heart, but he had a gambling problem. Money was tight." Cheerilee blinks as she hangs on Anon's every word. "I learned how to penny-pinch wherever possible. Then, I graduated high school. I had good enough grades to be accepted into a small college a few towns away with a scholarship, and I eventually got a degree in accounting. I moved out of my dad's place, got a job as an accountant (surprise surprise), and then... I lost it all in an instant." Without being prompted, Anon pours himself one extra shot just for the hell of it. "Anyway, was that what you were looking for?"
"Anon, I... wow."
"Come on, it wasn't that interesting."
Cheerilee slams her hooves onto the table and lifts herself up in an attempt to convey her sudden anger.
"You mean to tell me you have a COLLEGE DEGREE, yet you still act like a fool in my classroom?!"
Anon laughs again, this time shrugging as he does so.
"I passed your stupid quiz the other day, didn't I?! I know how to study, but I never said my professors liked my attitude!"
Cheerilee glares at Anon for a few moments before sitting back down.
"Sure, whatever."
"Hah. Anyway, back to me." Anon pours himself two more shots and downs them like water. "Why are you so tired all the time?"
"Heh, that's an easy one. It's because everything SUCKS, Anon."
Anon grins at her through half-lidded eyes.
"Come on. You can do better than that."
"Well, that's the truth. Everything sucks. I thought being a teacher was my calling. I love seeing students excited about learning, and I love watching them figure things out and grow up right in front of my eyes."
"You sound like you'd make a great mother."
"Pfft. A sweet thought, but that's not gonna happen. Not at my age." There's an awkward silence for a moment before Cheerilee shakes her head. "Anyway, it's been getting harder and harder lately. It's like the kids don't have any drive to learn anymore. They don't care what I say. I'm doing the best I can, but with the EEA breathing down my neck... ugh."
"What's the EEA?"
"The Equestrian Education Association. They make all the big-shot rules about schools in Equestria."
"And I take it they make it hard for you to do your job?"
"You don't know the half of it. Between that, and the pay not being very good, and YOU..." Cheerilee closes her eyes and downs another drink, ready to take her turn. Her face is becoming more and more flushed, and her demeanor is "loosening up" even more. "Anyway. Hmhm. Why are you so rude all the time?"
"I'm not rude ALL the time. Just when I'm around those that I really really like, or really really don't like. It's fun watching those that I don't like get pissed off about it. Those that I do like usually know me well enough to not take it seriously."
"And which one am I~?"
"At first, you were the latter. You've become the former since, though." Anon's cheeks go a bit red, but whether that's due to his words or the alcohol is up for debate. "Either way, I just find it easier than wearing my heart on my sleeve. Too easy to get hurt, you know? I make an exception for children though, they don't deserve my sarcasm."
"How noble," she says in a mocking tone.
"Whatever, Lee." Anon quickly downs two more shots, clearly doing better than Cheerilee at this point. "How old are you?"
"Didn't your mother ever teach you not to ask a lady her age?" Anon gives Cheerilee an unamused stare. "...OH! Oh I am so sorry."
Anon laughs out loud again.
"I'm kidding. Keep going."
"Well, I'm thirty-four years old and counting. Happy?"
"Wait, really?"
"I'm well past my prime, Anon."
"Bullshit, you look great, Lee."
Cheerilee looks at Anon in complete shock for a moment. She is most likely blushing, but it's almost impossible to tell through her alcohol-induced flushed cheeks.
"Th-thank you..."
"And before you waste one of your questions, I'm only twenty-six."
"...Well, you're younger than I thought."
"Is that a problem?"
After a moment, Cheerilee smiles and starts laughing for no particular reason.
"Not at all!"
Anon smiles back, patiently waiting to see if Cheerilee takes another shot. After she calms herself down, she does.
"What do you plan to do for work? O-once we're done with our lessons, I mean."
"Don't know. We'll see if my accounting degree can be of any use, but considering it's from another world, I've got my doubts about that. I'll find something, though. That a good enough answer for you?"
Cheerilee pouts, and it's surprisingly adorable.
"You're a lot less sure of yourself when you're drunk."
"Or maybe I'm just not hiding my true self in here." Without saying anything else on the subject, Anon takes a couple more shots. "Apart from financial security, what's your biggest dream in life?"
Cheerilee smiles and mumbles to herself in a drunken manner for a moment before focusing enough on Anon to respond to his question.
"The gala."
"The... gala?"
"We talked about it earlier, dummy! Ever since I was a little filly, I've wanted to go to the Grand Galloping Gala!" Cheerilee rests her head on the table, a look of longing on her face all the while. "I want to wear a pretty dress and eat the high-class food and just get to be where the actually important ponies are." Anon stares at Cheerilee for a moment or two, though she doesn't notice. What she does notice is a golden ticket being placed on the table right in front of her nose. "H-huh?"
"Celestia sent me two. Twilight already has one of her own, so, you know."
"..." Cheerilee doesn't move. Instead, she sits in her seat as still as can be, her eyes trained on the ticket. Her pupils widen and begin to sparkle, a tiny, involuntary squee leaving her mouth all the while. Eventually, she reaches out to poke the ticket. It does, in fact, react to her touch. Seeing this, she reaches out again, this time picking the ticket up. Sure enough, the ticket is real. "Anon... I..."
"Don't get emotional on me Lee, you're-" Anon is cut off by Cheerilee sliding around the booth and giving him a sloppy hug. "Drunk."
"Thankyouthankyouthankyouthankyouthankyou~!"
"Come on Lee, you're gonna be really embarrassed about this in the morning."
Anon practically pries her off of him and holds her at bay until she finally settles down enough to sit on her own.
"Itsh... my turn now, right?"
"No, no I think we're gonna call this a draw. I'm cutting you off."
"Aww, come on!"
Before Anon can react, Cheerilee fills all three shot glasses and pours them into her mouth simultaneously. Seconds later, she sprints to the restroom.
"...Yeah, that's about what I expected." Anon nonchalantly reaches for the glass of whiskey, which is still about half full. With a shrug, he pours the rest of it into his mouth without showing any sort of strain. While there is a slight hint of pink to his cheeks, it doesn't look much worse than after their first bottle. "These ponies cannot hold their liquor. This crap is basically water compared to the stuff back home."
Cheerilee groans as sunlight pours through her window and into her eyes. She slowly begins to sit upright, but she is immediately hit with an awful headache. It's been a long time since she has felt this way, but she knows damn well what this feeling is. She's hungover.
...Wait a minute. She has work today!
Doing her best to ignore the throbbing pain in her head, she glances at a nearby clock. She's darn near two hours late! Booking it out of the bedroom, she immediately rushes towards her kitchen table to grab her bag.
"Hey, Anon."
"Morning, Lee."
"...W-wait, what?!" Cheerilee jumps in place, only now realizing that Anon is lying on her couch. He starts to stand up, stretching as he does so. "What are you doing in my house?!"
"You got really sick last night, Lee. I had to carry you home. Then I had to hold your mane for you while you vomited." Anon sighs, and Cheerilee notices the dark bags under his eyes. "All night long."
"I... oh Celestia, I am so sorry."
Anon waves her off.
"Eh, I ended up crashing on your couch, so we'll call it even."
"Well, as much as I appreciate it, I need to get-"
"Stop."
Anon steps in front of Cheerilee, cutting her off right as she was making her way towards the front door.
"Anon, I need to get to school!"
"I already got a substitute for ya. As far as anyone else is concerned, you weren't feeling well during our lesson yesterday and asked me to inform everyone that you were taking the day off."
Anon winks.
"I... look, I know you mean well, but I can't afford to-"
"To what, pass out in front of your students?!" Anon raises his voice at Cheerilee, catching her by surprise. She is speechless as she looks at him with wide eyes. "Look at yourself, Lee. You've barely been able to make it through a REGULAR school day. Can you honestly tell me that you'd be able to get through the day in your current condition?" Cheerilee opens her mouth to speak, but no words come out. Her gaze slowly falls to the floor. "That's what I thought."
"...You don't understand, Anon. I need the money."
"I'm sure you do. But you also want to be an exemplary role model for your students, right?" She looks back up at Anon, her eyes growing misty. "It's just one day."
"...Just one day. Right."
"Now get back to bed. I don't want to have to watch your old mare ass all day long."
"H-hey!" Although she is at first offended, Cheerilee surprises even herself when she catches herself giggling at Anon's insult. It looks like he's right back to his usual self after all. "Goodnight, Anon. Or, I guess, good morning?"
Anon just smiles and holds one hand in the air as a wave goodbye, opening the front door in the process.
"See ya, Lee."
Cheerilee smiles back at him as the door closes behind him. Although her memory of the previous night is fuzzy, she remembers being really, really happy for some reason. She just shakes her head and walks back into her bedroom, ready to go back to bed and hopefully sleep off her hangover.
And that's when she sees the golden ticket sitting on her counter.
"...Sweet Celestia." She grabs the ticket and gingerly turns it around in her hooves. "I'm... I'm going to the Grand Galloping Gala." Unable to contain her childlike excitement, Cheerilee begins to trot in place and squeal. "I'M GOING TO THE GRAND GALLOPING GALA!" It takes her some time to regain her composure, but that headache of hers speeds up the process dramatically. She places the ticket back down on her counter and crawls into bed, her exhausted eyes falling closed almost immediately. Sleep overtakes her, but not before she mumbles one more thing beneath her breath. "Thank you, Anon."
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Great chapter, very much enjoying this. This was a fun way to get out a lot of exposition.
I'm still waiting for Anon to go through her bills. I saw it happening since she questioned how she owes more money!
Adorable chapter. The characters are written well & consistent with their personalities & reactions.
Was the insult calling her old or a donkey? Or both?
She was a friend, and then became someone he doesn't like? I think those terms should be switched. Alternatively, Anon is drunk enough to switch the order.
The money mystery persists! And now it’s revealed that our guy is a financial wizard…
11713170
latter: really really don't like
former: really really like
11713170
No this is correct. He is saying he didn’t like her “latter part of the first statement ” but now he does “former part“.
11713167
I bet he took a peek while she was passed out.
11713228
I bet that's not all he looked at.
I really like this characterization of Cheerilee. 👌
cute
11713268
Ikr
This site has such a wide range of character takes that make jumping from story to story so refreshing, each new personality is so interesting.
Are paid sick days not a thing in Equestria? Yikes.
Huh, it’s funny I usually dislike this trope in other fandoms.
But written as a good/great HiE story this completely clicks for me.
Looking forward to more chapters and an explanation for the bills. (And I really hope anon didn’t go snooping around, because that would be such a foreseeable plot point.)
Alright, I am going to guess what is happening here:
1. Cheerilee is being defrauded on her house payments/other obligation by her landlord using her publicly available information to gouge her monthly payments based on her income (which has just increased due to Anon). My guess is that it is the Rich's using their influence on her in order to keep her from being able to act freely by keeping her under financial duress.
2. Anon is going to use his accounting background to discover the financial crime being perpetrated against her, perhaps the sudden increase in her income (and the subsequent increase in her costs) being used as critical evidence in the case.
3. All of the things that Anon has done for Cheerilee and vice versa result in a romance.
4. Anon is revealed to be J-anon D Rockefeller.
Honestly, not very sure about a lot of these but I've a good feeling about #4.
11713503
Oooh, that is a good point. I bet that Anon will not be able to figure out why Cheerilee is so sensitive about her financial situation, which will be the inciting incident in interpersonal conflict between the two after Anon checks the public records.
Maybe there's a GED for accounting
Great chapter as always!
I see myself in this story…
And not as the Anon…
Such a great representation of what a teacher has to go through.
Ah lawdy they gonna be frolicking together before we know it.
Wow, pony bars are something else, selling whiskey by the bottle, lol.
11713808
I'd buy it by the bottle if it was cheaper than by the shot and I had enough friends to enjoy it with. Sadly... I don't.
Top cute. Cheerilee deserves hugs, pets, reassurings, and most importantly gala tickets.
Good story! Absolutely enjoying it so far, keep it up :)