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Summary:

“See, this can-do attitude…”
Is why you’re my favorite, the voice echoed in Jester’s brain, making them wince.
“...is why you worry me so much."

_________

Jester does not usually make it a habit to care about contestants. What's the point? They will all end up the same way. But Jester wouldn't want anyone to end up the same way they did.

Notes:

(See the end of the work for notes.)

Work Text:

Jester had never been interested in contestants. At least not in a way that went beyond whatever intel they needed to prepare for the fights they were scheduled for. Sure, the current newcomers made quite a buzz around the dungeons, but Jester didn’t even bother to learn their names until they absolutely had to. And even then, their interest was nothing but idle.
Though there was actually one contestant that really intrigued them.
No, “intrigued” wasn’t quite the right word. Worried them.
That contestant was none other than the spellcasting extraordinaire, the social media medium, the one and the only - the Witch.

No matter how you looked at it, Witch was the most talented out of this new batch of contestants, shining even brighter than the beloved scatterbrained genius, Inventor. The way she juggled her spells, chaining, intertwining, synergizing, and then wrapping it all up with a flourish, like a glittering bow on a present - watching it happen live was like nothing else. She even figured out a way to materialize the dice and use them as projectiles, to the delight of the audience and the aggravation of anyone on the receiving end of it. Of course this unprecedented show of entertaining prowess could not escape Lady Luck’s notice. And so, she would make it a point to turn the difficulty up for Witch specifically to nearly unbearable levels. Jester would often see her personally throw a wrench into otherwise perfectly executed runs: giving her abysmal rolls while giving the opponent all the right ones, cursing the most crucial equipment in the most crucial moment, arranging the floors in a way that made health management near impossible. And it was always right when things seemed to go well, right when the victory was within her grasp. It’s to maximize the entertainment value, Lady Luck would explain. Duh. As if she needed to explain herself, or explain such a simple concept to the person who’s been the witness to the process for hundreds of years. It was true that the level of Lady Luck’s personal involvement in the runs depended on each contestant’s skill level and entertainment potential. Sometimes it was enough to change up the rules in a way that would put the contestant way out of their comfort zone, and let their panic do the rest. Not in this case, that much was clear. But it was also clear that Lady Luck took special interest in this particular contestant.

Of course talent alone wouldn’t put this poor soul on the showrunner’s radar.

Unlike the other four, Witch didn't seem to join the contest with a clear goal in mind. Even when she did, after some deliberation, conjure a more or less tangible idea of a prize, it sounded more like an excuse (seriously, of all things to sign your life away for…). But nobody comes to a place like this without expecting something in return. Even the most apathetic of the minions, who never intended to claim the contestant role, came here because there was something the dungeons could fulfill for them, be it shelter or enrichment. And Witch was anything but apathetic. No, she always gave it her all, and sometimes more. Lady Luck could ramp the difficulty up to infinity, and she would just take it with her bright influencer smile and an inspirational quote up her belt - as if it was a compliment. And if there was anything that Witch seemed to enjoy and pursue, it was compliments. Everything she did, from her flashy, sparkly performance to her polite and upbeat everyday attitude, was to make sure she left the best possible impression on anyone who could be watching. She would often get fussy about social media, ratings, comments, articles, audience’s feedback, anything that could quantifiably gauge how she was perceived by the public. Of course it was impossible, or at least very hard, to access this kind of outside world information for a contestant, but she always found a way. She was, after all, very talented. And well, that in itself wasn’t the issue. The issue was her other, more available, more immediate, and therefore more important source of validation.
Lady Luck.
This was frustrating to watch. Everybody had a weakness, and Lady Luck was especially good at identifying and weaponizing those. But here she wouldn’t even need to try. Witch had a glowing red weak spot right where her heart was supposed to be in that new cubical body of hers, and boy, Lady Luck did not hesitate to hit it again and again, with little to no retaliation. And where would that retaliation even come from? That girl was swallowing it all up like candy - from undisguised insults to backhanded compliments to genuine occasional special treatment. Lady Luck always made sure to mention at least in some way how Witch was her favorite, how she expected great things from her, how she was the star of this show. And it’s not like it was something unusual for her to say - what was unusual was that this time she actually meant it.
And normally Jester wouldn’t care. But it all seemed way too familiar, and therefore way too unbearable.

So the moment the familiar pointy hat poked out of the dorm room’s door, they launched themself bouncing in that direction before the doubt had a chance to settle in. It was time to have a little talk, monster-to-adventurer.

“Hey! Hey you, yes, you, the purple one!”

Witch flinched, but before she could turn around, Jester floated over her head and faced her, suspended upside down. An unnecessary but delightful thing to do when you have the ability to float.
The poor die looked dreadful. Which was no surprise - her losing streak was now at 63, an absolutely unprecedented number of losses back to back (most gave up way before that). She, of course, was taking it with a smile, like she always had, but it was obviously taking a toll. More than just that - in her most recent attempt she had finally reached the dungeon boss, for the first time in weeks and weeks of trying. But either due to the pressure or exhaustion, she, the illustrious magical prodigy, who up to that point had lost by a hair to things outside her control, made an extremely preventable (and as such, extremely disastrous) misplay she just couldn’t recover from, and everything went crashing down. Lady Luck didn’t even need to do anything - probably because she’s already done enough for things to get that bad. Witch smiled through that as well - how could she not? There’s always next time, right? She was smiling now as well, with her most tired, most disoriented, most strained of smiles yet.
“Oh! Hi. You’re from the other day! Or, or the other week? Uh… Jokester, right?”
“Haha, almost got it!” Jester twirled in the air with a shrug. That reminded them a bit too much of the act they put on whenever they were called to spin the wheel though, and it was really not the vibe they were going for right now. So they cleared their throat and humbly floated down to the floor. “Jester. It’s Jester.”
“Jester! Right! Sorry, sorry, a lot on my mind right now. Like, um…" Her eyes were wandering. "Say, Jester. You don’t happen to know today’s staff Wi-Fi password, do you? Normally I’d ask Sorceress, but she still won’t talk to me after I broke her phone screen with a burning die that one time. Ugh, like she wasn’t the one who set it on fire… And nobody else seems to even care about stuff like that! You seem to be pretty high up on the hierarchy ladder here, so I just thought, um…Gosh, I’m just at my wit’s end here, you know?”
Witch sighed in exasperation, raising her arms up in the air. She was holding her phone in one hand and a double chocolate muffin in the other. Her hands were visibly shaking, and sometimes she would absent-mindedly squeeze the muffin, as if trying to type on it. Jester recognized that muffin. They did not have those in the cafeteria. No, those could only be found in the lounge room reserved for the staff, which contestants did not have access to.
That wasn’t a good sign. The dread in the pit of their stomach was growing stronger.
“Sorry, no can do! If I told you, Lady Luck would have my head for the unprofessional conduct, quite literally, I must add”, Jester giggled, glancing down to the muffin. “What’s that you got here, by the way?”
Witch shuddered, as if she just now remembered what she was holding.
“Oh, this? Haha, well, I guess I’m not supposed to have that… But Lady Luck said that I could go in the staff lounge and get one, because, ahem, that disaster of a fight was so utterly hilarious that I deserved a little treat”.
Jester blinked slowly, a lump forming in their throat against their better judgment. Was it anger? Did they feel that bad for this confused diceling?

Were they projecting that much?

Witch giggled apologetically, seeing (and probably misunderstanding) their discomfort.
“I should probably finish that before anyone asks questions. She really didn’t have to do that though. I mean, like… She gave me permission to take a snack from the lounge, but not the staff Wi-Fi password? Seems a bit arbitrary, doesn’t it?”
Jester swallowed the lump and coughed, but the tension still managed to seep through in their voice. “Well, "arbitrary" is the name of the game here, am I right?”

Witch batted her eyelashes. “Really? I thought it was “Dicey Dungeons”.
She paused for a moment, sizing up Jester’s confused face, and then burst out laughing.
“Sorry, sorry, that was a bit too cringe. Just thought I should try something new. This is something Warrior would say. He’s a really funny guy, very straightforward. The audience loves that, but I don’t think I could pull off that kind of format. I really need to step up my game though. A while ago I saw a comment accusing me of ripping off Sorceress. Can you believe that? What, just because we both have pointy hats, a cauldron and a social media account? Every witch has that! Ridiculous, like, I guess that's showbiz for you, but it’s been eating me ever since. So I’ve been thinking about how I can spice up my act. Cauldron and Magic Missile are versatile and reliable, but maybe next time I should go with something like… a flaming sword! Or maybe something along the lines of blood magic? That could be a fresh spin. Would help me with health management too. Oh, but then I’d be accused of copying Drake, and that’s the last thing I need after what happened last time…”

As she continued to ramble, Jester could feel the dread inside them build up and gradually transform into something else - annoyance. Is this why Lady Luck has been allowing Witch to get away with accessing her social media account for as long as she did, only cutting it off now that it’s funnier to do so? 63 wipeouts, and that was her biggest concern? Lady Luck wasn’t kidding, someone with priorities that out of whack really was the type she’d fall for. Jester would know.

Jester would know all too well.

“You’re… really taking this seriously, huh”, they forced the words out, smiling dryly.
“Well, of course I do. I have to, if I want to succeed!”
“Succeed?” Jester chuckled. “As in, win?”
“Hmm, well, that would be nice too. But that’s not all there is to success when it comes to the entertainment industry. You’ve been working here for so long, you of all people should know that.”
Jester smirked.
“Oh, I do know. And I’ve been working here for long enough to also know that success is not something you should come here for.”
Witch shrugged.
“I don’t know, I think I’ve been doing a good job so far,” she gave another one of her cheerful influencer smiles. “I just need to try a little harder, right?”
Jester could feel their stomach turn upside down. The nerve, the nerve! How clueless can one be?
“See, this can-do attitude…”
Is why you’re my favorite, the voice echoed in Jester’s brain, making them wince. Eugh.
“...is why you worry me so much. Just take that “try a little harder” mantra of yours. As far as I’m concerned, you’re the biggest tryhard out of all you newbies. Well, there’s also Robot, the unhinged workaholic. But even Robot knows its limits, as absurd as it sounds after its insane introduction statement. And last time I checked, Robot doesn’t have a losing streak of 63.”
Witch furrowed her eyebrow, continuing to smile even then.
“What are you implying?”
“63 failed attempts back to back, Purple, so you tell me. For how long will that “try a little harder” carry you? How much harder are you going to try before you realize what’s going on, or before you break, whichever comes first? You’re all doomed in the long run, I thought you’d catch on to that by now. What’s the point of grinding yourself into a dice paste for something you’re not going to achieve anyway?”
Witch scoffed.
“If that’s about the prize, I’ve said many times that it’s not my priority.”
“So what’s the end goal then?”
“Well, for now it’s about the journey, you know?”
“I seriously don’t. From what I can see, the journey hasn’t been treating you well either. You look like you died last week.”
“Well, I may be a little tired, but what’s new? It’s all a part of the journey,” Witch proclaimed, beaming like morning sun, and Jester could swear they saw the words visualize behind her in cursive on a floral background.
“Part of the journey, huh?” Jester could feel the venom in their throat about to spill, but it was too late to do anything about it. “Was casting Wooden Stake when Drake was at half health because you were too stressed and sleep deprived to assess the situation also a part of the journey?”

Something uncharacteristically dark and cold dropped a shadow on Witch’s ever so gentle face, but only for a moment.

“Gosh, I really messed up that one, didn’t I?” she sighed, her face mellowing out into an apologetic smile once again. “That was the most embarrassing thing I could have possibly done. And right when I reached the dungeon boss, too! I’m never going to live it down. I know I’m being roasted to the bone in the comments right now, even if I can’t check. Drake was laughing his butt off, that jerk!..”
She suddenly stopped in her tracks and bounced the muffin in her hand.
“That’s his muffin, by the way. It had a “don’t touch or else” note and all. Well, I hope that asshole likes the sensation of sinking his teeth into rubber, because that’s exactly what he’s getting for messing with a witch!” She threw the muffin in the air and twirled it on her finger, before taking a huge bite out of it. “Allez-hop!”

Jester could no longer contain the guffaw.

“Bahahaha! Wow, I can see how you’re her favorite. You’re this close to becoming my favorite as well!”
They straightened up, wiping a tear.
"Listen, normally I wouldn't care how you contestants decide to throw your lives out the chute, I'm really not paid enough for that. But just for you, a word of advice. In this place, it's not a good thing to be anyone's favorite. Especially hers. Whatever it is you want from her, she won't give it to you, at least not in a way that wouldn't compromise your dignity. So remember that next time you choose to accept one of her backwards little favors."
Witch trailed her gaze up and down, as if only now she recognized Jester's presence.
"Oooooh, so that's what it's about! You should have started with that. Here I thought you were doubting my ability!"
Jester sighed.
"I am doubting your ability - your ability to understand what mess you're getting yourself into by playing along with her whims."
Witch's signature apologetic smile grew even more apologetic, at this point almost guilty.
"Is it really that bad though?" she fidgeted. "I mean, you are right in that I'm having a hard time. I'm here because I like it here - I like putting on a show, even if the result is unfavorable and I have to do it all over again the next day. But even then, working so hard and having it go nowhere can get really disheartening, so it's encouraging to know that it doesn't actually go nowhere. That it's still entertaining - for someone. For her. When she says I did a good job, or even when she says I did a dreadful job, but I can see it in her eyes that she loved the way I failed, and she wouldn't love it if she didn't acknowledge the hard work preceding it - it kind of makes it all worth it, you know? I mean, she's a showrunner, the highest authority in this place, so it must mean something that she would put her trust in me, right?"
Jester let out a long, heavy sigh. Yep, it was exactly as bad as they assumed. Not a glimpse of self-awareness in that square little head.
"No, it doesn't mean a thing - because she doesn't put her trust in you. For her to do that would require her to see you as… something more. Something of her caliber. Have you seen yourself in the mirror? You're literally a die. A plaything. And that is all you'll ever be, the only thing that changes being your novelty."
Witch glanced down, awkwardly kicking the floor with the toe of her witchy yellow boot.
"Well, what if I don't mind? What if I like it?"
Jester clicked their tongue in exasperation.
"Of course you like it! Lady Luck's affection is larger than life itself, even the crumbs of it are intoxicating. But the moment it runs dry, you'll be left with nothing but your regrets, your wasted years and your chronic exhaustion - that I can see you're already developing."
Witch rolled her eyes and groaned - that alone wasn't enough to mask a yawn.
"Nudnik. You speak as if you have firsthand experience."
"Well, that's because I do", Jester laughed, a touch bitterly. "Didn't I mention I was a contestant once? I know all about winning, losing, giving up, and dedicating it all to her. There's a reason I'm worried about you, and not, say, Inventor, who has her own thing she's focused on - well, when she's focused, that is. She could care less what Lady Luck has to say about her as long as she has her gadgets and her pursuit of knowledge, and as long as she's allowed to study that trap door on the main stage or whatever else. Same with the rest. Sure you're all doomed in the end, but when they inevitably give up it'll be much easier for them to take the transition to their new lives, because ultimately their happiness was never tied to that fickle creature that is my boss. In fact, they'd still be able to achieve whatever they came here for, even if not in the way they imagined. But you? What will you do when that day comes? How will you cope with the eternity of emptiness that will now be your life? Better start thinking about it now so that at least you get a fulfilling hobby out of this."
Jester crouched slightly, lowering their head as close as they could to Witch's level, the bells on their hat jingling with a gentle, sympathetic tone.
"Listen, Witch, I just want to warn you as a fellow once-contestant. Lady Luck is not like you and me. She's not human. She's not even a monster. She's literally a law of the universe in a beautiful wrapper, something much bigger than we can comprehend - that she lets us comprehend. So are her emotions and decisions. Being in her favor is not meant to last or bring you solace, and it's never for your sake. And you might think that it's worth it, that you're fine with such an arrangement. It's tempting to think so because it feels so good. But I would strongly advise you to… Why are you looking at me like that?"
Witch was staring at Jester with her huge buggy eyes, lit up by the spark of realization. With a grin the size of the universe she pointed her half-eaten muffin at them and exclaimed:
"Yep! You're in love with her."

Jester was in the business for long enough to train their face so that it wouldn't betray any emotion in moments like this. Like a crashing wave, flush hit the rock of their rehearsed smile, not an ounce of color seeping through.
"Well, I'm contractually obligated to neither confirm nor deny, but… Where did that even come from?"
"Oh," Witch giggled coquettishly. "You see, I'm just very good at divination."
"...Divination."
"Yep! It was something I did a lot before coming here. My followers really liked it! A lot of it had to do with like, relationship advice. I'll admit I'm a little out of practice, but if you want to, I could try and predict your fate!"
"My…fate", Jester mumbled, raising their head, only to be met with a cascade of bright ruby locks right in their face.

Lady Luck was towering over the two, and, as if her size wasn't enough to assert dominance, she decided to top it off by floating close to the ceiling, her arms behind her back.
Jester scoffed. Show-off.
How long has she been there? How much has she heard? Did it even matter? With someone like her, no amount of secrecy seemed to matter, and Jester knew that better than anyone, but it still left a bad taste in their mouth. Probably a side effect of still, after all these years, being a person with feelings.

"Anything interesting you two are discussing?" she sang with a playful grin. "Anything important enough to keep my contestant behind her very busy schedule? Witch, darling, you were supposed to be in the greenroom five minutes ago. We may have eternity, but we don't have all day!" she pointed at the phone in Witch's hand. "And what's that you got here? Are you begging my minions for passwords again? I thought we'd talked about this. Guest Wi-Fi should be good enough for you!"
"But it's not even connected to the outside network!" Witch protested meekly, but with a lot of conviction.
"And you want everything at once, don't you? There's no time for this nonsense, my dear, the shooting will begin without you and your fans will be very disappointed! So hurry along, and finish that muffin already while you're at it. Drake knows what you've done and has been begging me to slot him as your dungeon boss today. I said no, but if I'm forced to think about it for another 10 seconds, I might just change my mind!"
Without a single word, Witch threw what remained of the muffin in her mouth, together with a little wrapper, and scurried away, wrapper hanging from her mouth and flapping in the wind. Lady Luck saw the diceling off with her eyes full of utter endearment, impossible to tell if genuine or ironic.
"There she goes, my precious little people pleaser, clueless as ever." She turned to Jester. "And someone here has been trying to disturb the perfect clarity of that untouched mind. Jester, buddy, what was that about? It's unlike you to care that much about some contestant."
"Well, it's unlike you to play favorites with the contestants, Milady, yet here we are", Jester retorted, arms crossed, smile sharp like a knife.
A mischievous, almost dangerous, spark lit up in her eye as she drew near and bounced a bell on Jester's hat with her finger.
"Oh? Oh? Is that jealousy I hear? Jester is jealous?"
“Jealous?” Jester let out a caustic chuckle. “Is there anything to be jealous about? What have you given her that you haven’t already given me and that I haven’t regretted a thousand times ever receiving? All I want is to save another starstruck fool from getting caught in your web of divine indifference, hopefully before they have a misfortune to learn what that is - if I can help it. I’m more than fine with being here alone.”
Lady Luck threw her head back laughing, her fingers now holding Jester’s hat bell in a tight clutch.
“My, so the little Witch was right!”
Jester looked to the side with barely concealed resentment.
“Don’t pretend to be surprised. You know. We both know. And last time I checked,” Jester’s voice switched to a mocking intonation. “It doesn’t matter.
Lady Luck let go of the bell, which bounced back up, jingling a whimpering tune.
“Well, it’s a good thing you remember,” she smiled. “Because I still stand by those words. It’s just like you said, Jester. I am not a human, I am not even a monster. Any human emotions you may feel towards me are your choice and your responsibility. And trying for hundreds of years to make them my problem will take you nowhere. See, my mercantile, validation-addicted little Witch doesn’t seem to have that problem,” she looked up to the ceiling for a moment, as if weighing something in her mind. “...Yet. And that’s why she’s my favorite. But don’t you worry…”
She cupped Jester’s hat bell in her hand and touched it gently with her lips.
"...You will always have a special place in my heart.”
Before Jester had a chance to even react, she pulled away with a comical shrug.
“Wait, I don’t even have a heart. Oh well!”
Yep. There it was.
Jester cracked a wry, if a little tired, smile.
“Very funny, Milady. Maybe you should be the jester instead?”
“Har, har,” she grumbled, looking at her beeping wristwatch - it hadn’t been there just a moment ago, but something like that never really stopped Lady Luck. “That’s my cue. You should also be going. If I’m not mistaken, your job implies responsibilities that are not limited to chatting with cute girls in the corridors. Maybe you should follow a certain someone’s silly little advice and… try a little harder. You know, for a change.”
Jester opened their mouth, but Lady Luck was already gone - disappeared into thin air, leaving behind nothing but frustration and heat on their face.
Jester was in the business for long enough to train their face so that it wouldn't betray any emotion in moments like this. Well, they certainly didn’t train hard enough.
They slapped their burning red face with both hands and groaned. The groan eventually turned into a giggle and a nonchalant shrug.
“Welp! And with that little trick I achieved absolutely nothing - and embarrassed myself before a contestant and my boss, to boot. Truly my luck is a joke!”

Cheerful game show music was now blaring from the speakers in the corridor. Today’s episode has started. Lady Luck was presenting Witch, sending quip after quip in her direction. Witch responded in her usual polite manner. She sounded like she still had a muffin wrapper in her mouth.

Jester clenched their fists.
“...And a jerk.”

Loud microphone feedback noise swept through the corridor, making the doors tremble.
“Jester, darling, do you think I didn’t hear that? Do you want to say it again? Run it by me? Hm?”
Jester burst out laughing, pumping their fist in the air.
“You are a jerk, Milady! A jerk! And I hate you! I hope you stub your toe!”

They turned around and immediately stubbed their toe on a broken piece of a catwalk that hadn’t been there just a moment ago - in fact, it had no business being there at all. Thief, another contestant, shot them an angry glance and hissed, before swiftly pulling the piece of scrap into their room and slamming the door shut.

Oh, Lady Luck, you’re just too much.

Still laughing hysterically, Jester bounced through the corridor like a spindly jingly rubber ball. Well, that whole morning was a disaster. Maybe they really shouldn’t have meddled, maybe they should have minded their business as usual, aloof and above it all. This has always worked for them, after all.

But maybe…
Maybe they just needed to try a little harder.
For a change.

Notes:

This fic is loosely based on my own playthrough. 63 was my actual losing streak on Witch's elimination round (together with 20+ losses on her ep.1 which I didn't mention here), and the Drake situation happened in one of the playthroughs, although I don't remember if it was Witch or Inventor.

But mostly I just wanted to write some gay drama ¯\_(ツ)_/¯

Special thanks to my friend Rae (https://archiveofourown.org/users/mssrmerrow/pseuds/mssrmerrow) for proofreading!