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I wouldn’t Bet on it (but I’m Wishing all the same)

Chapter 2

Notes:

I’m back!! Sorry I’m a full week late… this chapter is longer by a few k as a present though! (I didn’t do it on purpose)

Thank you again to Way_Back_In_July for helping sm and listening to me yap about this SO MUCH. I love you sm!!!

Okay so lwk it deleted all my italics again, and then when I tried to add them it made all my writing one huge paragraph, and that’s torture to the eyes, so there are just unfortunately no italics in this chapter. Which I hate. But we’ll have to cope (I’m sorry!!)

Okay with that, enjoy!!

(See the end of the chapter for more notes.)

Chapter Text

“Will, if you want a boyfriend, you’re going to need to actually talk to guys. That’s how it works.” Max’s voice crackles over the staticy line of the phone, her voice warm where for others it would be dry.

She’s right. She usually is, a fact she reiterates regularly.

Will sighs, kicking at the uneven ground beneath the bench he lies sprawled on out back. His break must be almost over by now, he thinks dully.

Max sighs right back, before “You’ve got to put yourself out there!” He can hear her exasperation loud and clear through the phone, can nearly see her, hair wild, eyes wide, and fingers snapping in his face for attention.

Will doesn’t know how he even let himself get to this point. You mention to Max once that you’re lonely and she goes on a tyrant.

You see, putting himself out there as she so simply puts it, is out of the cards. Obviously. This should go without saying.

Not to sound like one of those loser girls in romcoms before they get their makeover montage, but Will’s not just able to become confident.

That’s just not how it goes. And it’s fine. It will be fine. He can barely excuse a customer when they order something that the kitchen’s out of, let alone, put himself out there.

And even if he could, there’s not much to want, he knows that. Will’s just Will.

Too tan to be pale but not enough to be tan, average height, muddy brown eyes with just enough other colours to be generously called hazel, and hair that’s not quite straight or wavy.

That’s not exactly worth the extra effort of putting in all the first moves, all the dates, if it even got that far.

He’ll just deal, if he ever gets a boyfriend it’ll be because the guy found him, the guy asked him out so Will knows he isn’t making it up or reading things wrong like he always does, and then things would end up good.

And that would be fine, and if the situation never comes along, then he’ll just stay single. Which is also fine.

Max doesn’t think so though.

Max seems to be reading his mind (something she has a knack for) and her voice softens further from over the phone line, “Will, you can’t just wait for somebody. It doesn’t work like that.” He can barely stand the pity dripping from her tone.

He probably shouldn’t sit out here on his breaks. Given that it’s just a lavish version of an alley, and he’s sprawled out on a bench and on his phone. Oh, and it’s like, night.

He could get, like, kidnapped, or something. Or, wait, would that be adult napping?

“My break’s almost over.” He mumbles into the phone, forcing himself up into a sitting position. Only half an excuse to avoid this conversation.

Max can always tell when he’s stalling, so he doesn't even know why he bothers.

But his break really is probably over, and punctuality is important. He just barely scored this job, and like hell if he isn’t gonna try to keep it. That and Robin’s shift starts right about now, so at least he’s got that to look forward to.

“Will.” Max’s voice cuts back in, stern and the slightest bit worried at the edges. He can hear the traffic from her apartment through the phone, the sirens rushing down her street.

He knows Max means well, but avoidance has always been awfully enticing to him.

“Yeah- yeah, I know.” He says. And he does. He does know that she’s right, some perfect guy isn’t going to just fall into his lap and ask him out. That’s not how the world works. Regular people aren’t that lucky, let alone him, with just about the worst luck possible.

But seriously, he’s heard enough about this from his mother, and Jane, and Max, and Robin. On and on and on about how he needs to just embrace being a little confident.

Despite meaning well, they don’t seem to understand that you can’t just decide to do that.

“I’ll…try.” Is what he settles on instead of his excuses. Max calls them excuses at least, but he doesn’t think they count as excuses if they're valid.

That seems to be enough for Max, for now, that is, because she backs off.

“Okay, and when you get like a super hot boyfriend after taking my advice, I’ll need an ‘I told you so.’ Moment from you.” She orders, losing her sweet tone in favour of a stern one, even though she’s mostly joking. Probably…

He snorts in response, “I figured you would.” Standing from the rusting bench, and moving towards the back door, shining metal against fading white brick.

“Hey, you’re just lucky I’m not making you pay up for my expertise.” She jabs back as Will reaches the door.

Ignoring this, he says “Well my break’s about over,”
readjusting the phone to be propped between his shoulder and his ear as he shoves the metal door open with a lurch and screech of metal.

Stupid sticky hinges, Will’s been complaining about it for ages, but no one comes out here but him and the main cook when he comes out for smoke breaks, so no one else really cares that there’s a high chance Will eventually gets locked out in a dimly lit alley in the middle of New York City.

“I’ll see you sometime next week yeah?” He asks with a huff, stepping inside the somewhat clinical warmth of the Portique restaurant, heels clicking against the white kitchen tile. It always feels a bit like he’s stepping into the doctor’s office. All white and no one can be too loud. Oh, and expensive.

“Mhm, I think we’re all meeting up wherever Steve works.” Max responds, causal tone back at the mention of the party.

Will snorts again at that, “Oh you mean the new one, what’s it now?” He asks sarcastically, shuffling his way through the cooks and other waiters all dancing around each other in the fluorescent lit kitchen.

Avoiding the steaming pots and flaming stoves with practiced ease, and sending an apologetic look over his shoulder to Heather as he ducks around her rather unceremoniously to get towards the employee’s room and fetch his apron.

“A sex shop?” He supplies, under his breath so no one but Max will hear. Well he hopes no one hears but Max.

Maybe that joke wasn’t worth his job. And dammit, he was just talking about not getting fired!

“Finally working his passion?” He adds as he ties the starchy black fabric of his apron into a neat bow around the back of his waist.

“God knows.” Max mutters dryly, probably rolling her eyes. Finally picking up his phone again and holding it to his ear instead of with his shoulder, Will sighs.

“Well, I should be off by eleven.” He says at least a little warily, before adding “Give Jane my love.” leaning against the cream coloured wall of the empty employee room, well save for him and the large wooden table with its matching chairs.

“Sure, see you next week.” Max replies, the muffled noise on her end already show enough that she’s on her way to hanging up.

“Bye.” Will says quickly, because Max hangs up so goddamn fast, usually before he can get half his sentence out, but this time he beats her to it.

“See ya.” She bids, and with that, the line goes dead.

Sighing again, Will clicks off his phone and slides it into his back pocket. Routinely straightening his apron, checking the buttons of his shirt, and running a hand through his hair, before he plasters on the customer smile he has gained in the few months of working here, and walks out the door to begin his shift.

Robin is here, thank the lords. Clocked in by the time Will gets to the back to receive the tables he’s serving tonight, luckily, he gets the section just next to Robin’s.

When the head of the wait staff mentions this, Robin sends a comical grin Will’s way, waggling her eyebrows at him. Once their manager is out of sight, smacks him in the chest teasingly with one of the menus she carries, with a little “Let’s get to it then huh?”

Eventually though, the novelty of his friend at his side wears off.

Robin, who usually brightens up the dull and redundant shifts that are working at Portique with her ceaseless chatter about whatever it may be.

Whether it be the girl Will still can’t know the name of because it’s “a secret Byers! A woman’s gotta keep some mystery in her life!”, the movie she and Steve rented last week that was so bad that even Steve hated it, or literally anything else under the sun.

No, it wears off real quick once she gets word of his and Max’s previous conversation. (By word, meaning that Will, like the idiot he is, told her of his own free will.)

“Max’s right, you know.” She mutters under her breath, just loud enough to be heard by Will over the dull weavings of customer conversation, a little twist to her lips as she watches him in her peripherals, feigning that she’s even paying attention to her tables.

Well, she tries to look at him through the corner of her eyes, her wavy hair obscures most of her side profile from Will’s view from where they both stand. Backs pressed against the wall just behind the hostess stand.

Will lets out a sigh, avoiding her eyes, because of course she’s right. Ugh, they both are, but that’s just not how this works!

“Robin,” he starts firmly, turning back to face her swiftly, both of them now thoroughly ignoring their own jobs.

“It doesn’t work like that. I can’t just- get confident, or whatever.” He says quickly, and tries not to let his gaze wander away from her when she smiles somewhat patronizingly.

He’s right too though. It’s not just going to happen. Will’s been an unconfident loser that never dared make a first move for his entire life, and that isn’t changing now.

The fantasy geek, DND player has no reason to be confident anyways, it’s one of the greasiest rules of the universe.

Without a pause,“Then just pretend.” She says, shrugging, and turning to survey the tables.

Like it’s the most obvious thing in the world.

Pretend? The hell does that mean? Pretend to be confident? Will is fairly sure that’s not how that works.

Because if it is, then why doesn’t everyone do it?

“You can’t just pretend to be confident.” Will groans, rolling his eyes at Robin, and fighting the urge to throw his hands over his face. Because he’s in public, and on the clock, and the manager is so fucking uptight he might even fire him if he so much as looked like he doesn’t like it here.

“It’s something you’re born with, or you gain. I’m neither, so I just have to get over it.” He says forcefully, shrugging in what he hopes Robin sees as a dismissive manner.

“Sure you can.” Robin says, an almost chipper tone to her voice as her eyes continue to roam the restaurant floor. Scanning over the lights, the glittering silverware, the menus flicking in and out of sight.

“”Sure I can” what?” Will asks, eyebrows scrunching in confusion. Because seriously, if the solution to this problem was just being an actor, he’s going to be seriously pissed he didn’t know this earlier.

“Pretend.” She responds simply.

Here we go again, that’s not how this works!!

“Riiight, cause that works.” Will mutters, bitterness unintentionally creeping into his tone. He has to fight an involuntary wince this time at losing the uncaring tone. Whatever, he never really had it to begin with.

“Yeah, that is how it works.” Robin replies.

“Robin.” It’s not supposed to sound as pleading as it does.

She finally looks at Will again, pulling her eyes away from the tables to fix him in what is suspiciously near a glare.

A kind of glare that says you know this, duh.

“Yeah, sure, that works in middle school-“ Will starts, waving his hand dismissively, but before he can finish, Robin cuts him off.

“It works now.” She says, again, like it’s the simplest thing in the world,

What is she even talking about at this point?

“It works right now. That’s what I do.” Robin continues, fixing him in a wide eyed look as if she’s explaining to someone that they’ve been in a coma for a decade, and just aren't getting it. Hands raising placatingly, speaking slowly, and with an eyeroll of exasperation just on the horizon.

What? Well that makes no sense. Robin, pretending? Why would she even have to? Robin who’s talkative and smart and cool, what is there to even pretend about?

Sure, she had trouble accepting herself, but, like, who doesn’t? Will sure did. Does. But she moved on from it, grew, and now she’s happy. Going on dates with some mysterious and unnamed girl.

Isn’t this the point of all those stupid empathy lessons in middle school? That even the “popular kids” have issues?

Or the point of all the coming of age movies where the popular kids are all as lost as anyone else.

Well that’s stupid, Robin’s not popular. But the metaphor still stands. Maybe Will really would have no idea if Robin was feigning it all.

That instead of giving up the chance of even trying, like Will has, she went the other route.

A beat of silence passes, well, not silence. The room still bustles around the two of them. Plates scraping, polite conversation, drinks sloshing.

But Will stands silent, with his mouth opening and closing wordlessly in a way he’s sure somewhat resembles a fish, while the gears turn and whir around in his brain, Robin watching the room, casually.

“What?” Will finally manages, his voice doesn’t sound quite like his, far too strained for such a tame conversation, but he can hardly even take in the look she gives him in return before “Will!” Is being called from across the room.

His boss had instructed Will to get five menus, that his first priority was table 7b, and to treat them kindly, because apparently the parents are regulars. Code for loaded.

Will couldn’t care less about the financial state of one of the families he’ll hopefully forget by the end of the night, but he just nodded to his boss and got to the rest of his tables that had already filled up.

By the time he finally gets to the family at 7b, after taking the blur of orders from the surrounding tables, and managing a minor mishap that a small girl caused by dropping (sliding) her lemonade glass off of her family's table, it’s been nearly ten minutes of them waiting.

Any longer will have his boss on his ass, so he hurries up to 7b, heels clicking along the tile as he tries to look like he isn’t in a rush, plastering a smile back on and saying, somewhat breathlessly “Can I get you folks started on some drinks?”

Five heads along the table turn to Will. He never likes this part, it always makes him want to shift from foot to foot at the sudden attention.

This family doesn’t look extraordinarily remarkable, though he can definitely see the ‘regulars’ side of the parents. (Loaded)

Will always likes observing the customers. How they sit, how they laugh, how they walk. It’s a good way to improve his sketches, it has a way of making them feel more alive. That and he and Robin love to make up fake stories about random customers in their free time.

“Robin, that old guy is not a crossword guy, he is so one of those guys who plays chess in Central Park.”

“And that woman over there is having an affair with her girlfriend behind her husband’s back.”

“I bet you that teen girl there has a big sister who’s some famous pop star, and they’re going to become icon, music rivals when the younger one goes into rock.”

 

The two parents sit next to each other, both in maybe their fifties, the man with huge glasses that look as if they’ve been whisked out of a WWII documentary with how thick the lenses are, greying hair that’s flattened back, and donning a frown.

The woman to his right, presumably his wife, sits with her hands neatly folded in her lap, hair blonde, the type that’s just barely noticeably dyed, and pink lipstick pulling up into a polite smile.

Before Will can really take in his observations of the other side of the table, the older guy is already ordering one of their wines.

Here we go, ordering some Chardine, in some droning voice, bored and dejected, obviously upper-upper middle class. Probably an accountant or something, Will thinks.

Will just nods along, scribbling down the wine order, then when the woman orders a glass of red for herself, Will smiling and nodding as he writes down her order before he turns to the other side of the table.

There at the end, across from the mom, sits a teenage-ish blonde girl, beaming at an older girl seated beside her, giggling quietly at one thing or another, and paying absolutely no attention to the rest of her surroundings.

Will smiles a little wider at the pureness of it, before her mother whispers a little “Holly.” Jolting the girl into ordering. Will smiles, and jots down her Shirley Temple order.

Then the older girl, curly brown hair, sharp face, and an intimidating sort of air about her, she smiles, lips pursed at Will as she orders a Lime Soda, and then to her right for the last one.

He sits with his head turned away from Will, seemingly speaking to the older girl, maybe his sister. The only thing of the man in Will’s view lays his black curls, a little unruly, and falling across the shoulders of this dress shirt.

That black hair jostles as he whips his head around to face Will, an erratic kind of look in his eyes. He’s a man, around Will’s age, maybe a little younger.

His face is slim, sharp, and pale. He’s obviously related to the brunette girl, probably his sister. Their shared cheekbones that look about sharp enough to slice glass, enough to tie them as family. But as they sit side by side, their bony features and slender necks are just icing on the cake.

His face falls shadowed just a bit under the lights in a way that would usually make someone look gaunt or sickly, but he pulls it off. It accentuates the sharpness of his face. Well maybe it does make him look gaunt and sickly, but it’s just pretty on him.

What.

‘Pretty’? What’s he mean by that?? You’re the one who thought it dimwit. How should I know? A voice in his head chides, sounding suspiciously alike to Max.

The thought came on in a flash of flames, unwanted and unwelcome. No, not a flash, more like the gas leak before the flames. Slithering and damn near undetectable, slipping through walls and casual thoughts.

The man just sits there, mouth open, eyes wide, while Will clears his throat, shaking his head just a bit in an attempt to clear his fucking head as asks again,“Drinks?”

The man scrambles, snapping his mouth shut with a funny little pop sound, forcing his gaze down to the laminated menu in his lap, and gripping it with long white fingers that drum anxiously across the material.

Maybe this guy’s got insane ordering anxiety or something, Will thinks as he watches the man’s eyes flick across the menu frantically for no apparent reason.

The guy snaps back up, sudden enough that Will may have flinched if he were closer. His eyes on Will. They’re still wide and full of… curiosity? Maybe.

Maybe he’s just, like, sick. Will can understand. Or maybe this guy’s just really weird. Some people are just weird.

Either way, it’s none of his business he reminds himself firmly. It’s not like he’s never seen a weirdo in some shitty retail job he’s worked. It’s just a little more jarring when he’s surrounded by old people up to their eyes in fifty dollar bills.

Will attempts to school his face away from what he knows has formed as mildly startled and concerned, back into something more customer friendly as he awaits a response.

The man sits, mouth open, eyes on Will, and mind seemingly blank from Will’s perspective. That or so full that he can’t do anything about it.

If this were a cartoon or a little kid’s comic book, Will would be standing here, eyes darting from side to side, on finger pulling his collar to the side and exclaiming a very audible gulp.

But it isn’t, so Will does his best to continue awkwardly waiting. It can’t have been that long, maybe just under a minute, but it feels like this guy’s been staring at him in something skewed just off center of awe for about a century.

Giggles from the blonde girl ring out even louder now, as she rocks back and forth, eyes screwed up in amusement, while the brunette next to her just smiles, smiles in a way that seems craftier than before.

The parents watch on, the man bored, and the woman hurriedly shushing her youngest daughter across the table with urgency, neither paying any attention to their son.

“Uh, soda- yeah. Soda. Please” he finally says, snapping out of whatever paralysis he’d succumbed to for the past several seconds, voice squeaking up higher than it sounds like it usually does while his face contorts in embarrassment. Pink creeping up his neck and staining his ears, just barely visible under his dark curls.

So he does speak, although it pitched high and nervous, it was sort of cute.

What the fuck is happening to him.

Why is this happening? This is just some random customer, probably some rich, spoiled, straight, college kid, maybe he’s on some kind of new drug that daddy’s money got him.

Besides, Will isn’t one to crush on randoms, or anyone. There’s never been anyone. Well, with exceptions for 80’s movies’ classic male main characters, but those don’t even begin to count.

No real guy has ever meant anything, well, real.

Sure, Lucas and Jane and Dustin and Max could (would) all argue that there’d been “that one blondie in Highschool” but that’d been different because that was barely anything, just blushing and laughing.

They’d argue about the guy with the arm tattoo in his first college sketching class who always gave him gum, and offered to give him the notes, even though Will had them.

But that was one sided, the guy was just being nice, something Will discovered when he saw said guy tonguing some girl with ultra heavy mascara in the boys bathroom in the middle of his and the guy’s class.

Yeah, that “crush” ended real quick.

They’d argue that there was Carlton back in freshman year of college, but, again, nothing happened.

Well, it almost did. But that’s very different. Crushing on some asshole only to find out he was just "experimenting" doesn’t count by a long shot.

No, Will isn’t the kind of guy to pick up something like this for anybody, let alone some random customer. And he wasn’t going to.

Will just nods to the man, not even trying to write anything down on his stupid little ordering pad, before he’s practically fleeing the table.

Soon enough, he's bursting through the double doors into the wait area, double doors swinging shut behind him with a flap, breath far too hurried for speed walking a couple feet.

Metal tables ring just under the window that looks into the kitchen, the table constantly loaded and unloaded with plates, bowls and glasses full of steaming, boiling, freezing, and clinking food assortments for the staff to distribute to the tables.

What the hell is going on. Why is he acting like this? Will slips the order through to the cooks, eyes unfocused as he keeps moving.

This is seriously weird, why is he freaking out? Some random customer who only sat there and stared, and suddenly Will’s thoughts are consumed with “‘pretty’ and ‘cute’ “ when he’s just trying to do his fucking job.

Seriously, he’d be humiliated if it wasn’t so annoying.

No, it’s fine. He’ll just serve the other tables. That was his last one for a bit, but he’ll just wait in the kitchen. He can find something to keep himself busy.

Anything to keep himself busy. Why are you resorting to overworking your fancy job just to distract yourself from some guy you interacted with for a maximum of four minutes?

Shut up.

Will turns, mind made up, and sets off to the kitchen.

He’s going to be an adult about it, and ignore it.

He’s going to send table 7b’s order in, check in with the rest of his tables like normal, refilling water and answering questions about how cooked the steak is with a smile on his face.

And he is most definitely not going to let this random guy with gangly limbs and perfect white teeth ruin his night.

He’s not going to be locked into a frenzy of worrying and overthinking about someone he’ll never see again. Nope.

“Hey little Byers.”

Will nearly jumps through the ceiling.

Whipping his head around, Robin stands right behind him, damn near grinning in his scare.

“Jesus Robin!” He squeals feebly, spinning to face her. Her smile only grows. “What’s with you, jumpy?” She asks, leaning against the wall casually.

Jesus, if only he knew.

“Nothing.” It sounds about as unconvincing as if Will were to have said he has just developed the ability to fly.

“Mhm.” Robin hums, unconvinced. Her eyebrows drawing together as she looks him up and down.

They should both be working right now, but nobody’s yelling at them to get back to it, so Robin just stays where she is, surveying Will.

Shifting from foot to foot, he shoves his hands into his pockets just for something to do with them, trying to keep his face blank.

He is not going to hear the end of this if she gets it out of him.

A sharp breath escapes her abruptly, small but loud enough in the small space between the two of them to make Will’s eyes go wide. Her face lights up, her grin growing sly.

“I know.” Robin breaths, her eyebrows shooting up as she stabs her pointer finger into his chest accusatorily.

Swatting her hand away with the back of his own, Will frowns down at her before crossing his arms across his chest.

Not defensively, if you were wondering. Because there’s nothing to defend. Because nothing's happening.

“I don’t know what you’re on about.” Will mutters, but he can’t look her in the eyes. He’s always been terrible at lying. Ever since he can remember, Will has been awful at lying. Anyone could see through it like glass in a second.

“You’ve got the hots for some customer out there, huh?”

Will’s entire head snaps to face her in an instant.

“Lower your voice!” He squeaks, grabbing for her wrists desperately as if he can convince her. As if anyone could convince Robin of anything.

She’s definitely smirking now, teeth glinting in the white light, and brunette eyebrows waggling up and down suggestively.

“You sooooo do.” She trills, drawing out the word tauntingly as she tilts her head to look at Will while he tries once again to break eye contact.

God he knew this would happen.

Will fixes her with the sternest stare he can muster, one that does nothing to discourage the smug look
plastered across her face.

Will finally just sighs, not for the first time tonight, and says “Well, think what you must.” Because he’s not going to lie again. She’ll just see through that and pester him about it. Not like she won’t anyways.

“Awww, don’t you worry, I will.” She simpers, practically bouncing on her heels in front of him.

The night is going just about as hellish as he could have imagined. Robin, did not in fact, back off. If anything she advanced.

Will had no idea one person could talk so much about one thing so quickly in such a short span of time, but this is Robin they’re talking about, so he shouldn’t really be surprised.

By the time Will manages to get another break between bringing trays of steaming food to and fro, taking more orders, and showing old ladies to the bathroom (one of which, Will has had to have yet another talk to Robin about, because she cannot keep calling the old lady regular her grandma just for tips and perks. But she claims it’s “morally debatable”) Robin has already managed to get just about everything out of Will.

The “What’s he look like?” Was quick to be answered. She damn near kicked her feet and giggled when Will warily described how his freckles and cheekbones provided a striking contrast.

Well, Will didn’t tell her that he thinks it’s striking, he’s not that stupid. He told her it was “nice” but he’s pretty sure she saw through it in a second.

Then came the “Well how was he acting?”

And then “Weird how?”

Will groans, hands over his face in a feeble attempt to block out Robin’s prying. “I don’t know. Weird weird.” He mumbles through his hands.

“Like he kept flinching and his eyes were all wide and he could barely talk.” Will tries, lifting one limp hand off of his face to gesture meaninglessly.

Stuttering, that’s what he was doing. Well some people just have a stutter.

“Wait, that sounds bad. I’m not making fun of him or-“ Will rambles, sitting back up quickly from his slump over the creaky break chair.

“Yeah I know.” Robin cuts him off, waving a dismissive hand over in his direction.

“But like, how weird was he being?”

Will’s eyebrows raise, his face still half covered with one hand. What is she even on about now?

Ugh, if this stupid guy hadn’t walked in and made Will a blushing mess, then he wouldn’t be in this position.

Him and Robin would be complaining about the really condescending guy who always comes in on Saturdays and always treats the server like it’s their first day even though Will has served him his stupid Clam Chowder about a million times.

Or Robin would be talking his ear off about something else. Literally anything else. But noooooo. Will is forced to sit here, wallowing in his own despair and patheticness as Robin interrogates him about this guy.

“Ugh, I don’t know Rob!” Will exclaims, running his hands up off his face and into his hair, working through the lack of tangles just for something to do.

“Well, was he blushing?” Robin asks, her lips quirking up, her eyes glittering with something taunting.

What does this even have to do with anything? They’re trying to figure out if they’re accidentally being hugely insensitive to someone with some sort of illness or something, and now they’re talking about blushing?

Oh.

Ironically, Will is entirely sure that he himself is blushing now.

“Aha!” Robin gasps out, snapping two of her ring covered fingers, echoing around the empty room. Apparently Will’s flush was enough of an answer for her.

“Woah, Robin!” Will begins to protest, sitting up fully in a rustle of fabric and the screech of his chair.

Because she does not need more ammo. He was going to make it through her teasing him about some fleeting crush for a week, but now she’s got the pebble of an inkling that this guy likes Will?

He’s going to be sent out on some Robin manufactured scope out mission, given some lame pick up line, and told to “C’mon, get out there Byers!”

“Ah, ah, ahhh.” Robin tuts, waving her hand to cut off Will’s sputterings.

Will just groans quietly and shuts his mouth because he’s long since learned that talking over Robin is basically impossible.

So he just crosses his arms across his chest and waits for the latest blow.

“This is your shot!” She squeals, grinning in a way that stretches her freckles over her nose in a way that Will would enjoy to sketch later.

Pleasant thoughts are a fine distraction when Robin begins spewing absurdities that have to do with Will’s social life.

“Robin,” Will starts carefully, like he's about to tell a little girl that her puppy's just passed away.

“This is not my shot. It’s nothing actually!” He insists, hands waving about like he can convince her with gestures. It doesn’t seem to be working though, because her grin stays just as wide.

“Yeah right.” She snorts, “This is the perfect time to practice!

To practice. Yes of course, just go practice flirting on some customer Will! Ah that’s brilliant Robin, why didn’t I think of that?

Will’s hand flicks up to his face, fingers clutching at the bridge of his nose as he breaths deeper than he needs to.

“Robin, I cannot just-“ he starts, voice growing to strain in between complaining and exhausted. This is really exactly what he doesn’t need.

His Mom and Hopper (barely Hopper, but he’s quietly supportive) are on him to be happy and get a boyfriend. His Mom thinks he’s lonely or something.

Then Jane is encouraging him to try it too in that earnest but confused way about her where she doesn’t completely get where the issue lies in Will just not “getting out there”.

Oh and Max, threatening to get Lucas to set him up with some basketball guy if Will doesn’t get his ass in gear and do it himself.

Will has tried, really.

Okay, no he hasn’t. But he’s tried to try, and that still counts. It’s just different for him than his Mom, or Jane, or Max.

His Mom has known Hopper forever, and even though she’s had her rough patches, including the Lonnie era that everyone involved agrees was a mistake, she’s always kind of known.

And yeah, her and Jim danced around about it a bit, but at least they knew there was a possibility. Will doesn’t have that safety net.

What if some guy he catches feelings for is a total asshole who laughs in his face at the idea if Will could even manage to say it.

Sure, it’s cowardly, and he should be over it. It’s the 21st century for god’s sake!

Robin cuts him off yet again before he can finish his pitiful spiral or his sentence, Robin is standing in a rush of uncoordinated limbs and clumsy movements.

“Ooh break time’s over! Guess we’ll have to finish our little chat later.” Robin chirps, barely containing her growing smile as she brushes off her uniform.

Standing expectantly as though this is a usual occurrence, as if Robin ever cares about when their breaks end.

“I- hey Robin! I am not-“ Will sputters, standing too and following her brisk path to the door, trying to catch up to the bouncing bob in front of him.

But just as he makes it to the door, she swings it open, spinning more swiftly than Will would have thought she possibly could, stepping through, and then turning to face him. Her smirk ever present.

“Nope, gotta get back to it!” She sings, striding through the doorway without a second glance back to Will.

“Those tables aren’t gonna wait themselves!” She calls as she grows further down the hallway, leaving Will standing in the empty break room,

Well shit.

Robin does not relent. How could she? Will loves her, he does, he wouldn’t have even gotten this job without her, or to where he is in life all around (ugh sappy much) but sometimes he really just needs her to stop being so observant.

Maybe that’s the wrong word, because he’s witnessed Robin miss verbal implications about a zillion times. That or just ignore them.

But with Will? Waaaay different story. Will can say he’s not too stressed over school, instant hostile takeover of the conversation on Robin’s part.

It’s like she turns into a human lie detector just to see through Will with a magnifying glass, teasingly help him about whatever it is he’s trying to avoid, and then switch it back off in any other possible scenario.

 

But Will powers through. He only rolls his eyes when Robin waggles her eyebrows at him again from across the room when he goes to fill 7b’s drinks, and then again, and again, when he brings out their food.

He purposely keeps his eyes off of the twitchy, curly haired boy, keeping his eyes on the Mom, watching her tip back her wine glass hungrily, or on the youngest girl, chatting away with the brunette, her eyes bright and wide with a loud sort of giddiness.

He keeps his eyes on the trays, on the tables, on the tiled floors. Water there, ordering there, back to the kitchen. Repeat.

It’s a simple routine, maybe not easy, but it’s simple enough. In theory.

But it’s different tonight.

Like everyone’s watching, waiting. For Will to slip up. For him to give in to his misreading of the situation. For him to approach the tall and gangly and undeniably pretty customer, and ask him if Will can have his number, just for him to laugh in his face and go tell his family all about it.

Maybe try to get him fired.

“Well, that wouldn’t happen.” Robin says calmly. Will has no idea how she’s so sensible during things like this.

Like, she can do her damndest to knock her sense of sense into Will, but the second that’s done, she switches it straight off.

One could call it mildly infuriating.

“But it could.” Will argues back, running a lemonade stained sticky hand up through his mop of hair, smoothing and unsmoothing it.

And he isn’t wrong. He could get fired for making a scene with a customer, because it would be quite a scene if he were to get rejected and laughed at in front of an entire restaurant.

“Will.” Robin says, firm and unwavering, a tone that forces his eyes back to her as he continues to fidget.

“I love you, I understand it’s hard, but this is your shot, you hear me?” She says earnestly, and Will gets the sense that she would be shaking him by the shoulders if they weren’t still in customer’s views.

“You can’t get better if you don’t practice.” She continues, her eyes locked on his in a way that’s only slightly intimidating.

Will let’s out a sigh on reflex. “But I can’t pretend. I can’t do it Rob.” He insists, trying to convince her with his words, his face as his eyes go wide, pleading.

Will says this, expecting her to complain, to tell Will he just has to get over it. And he’d probably give in, eventually. And say “I’ll try.” Like he always does.

And he would. He would try, and fail. He’d fall flat on his face and become the laughing stop he knows he is. Call him dramatic all you want, but it’s true.

A cop-out answer is better than none at all.

But that’s not what she says. Instead, she lets her eyes wander from Will’s, drifting up to the corner of the room. Without really thinking about it, Will follows her gaze.

It lands upon a particularly shiny green ceiling tile. Bright, but not unusually. Something that does not warrant her, and Will by association, to be staring at it so intently.

But before Will can manage to question whatever she’s doing, her eyes have snapped back to him along with her whole head. Her hair jerking back in his direction, so sudden enough that he has to suppress another jump of surprise.

“Then don’t pretend you’re confident.” She grins, eyes glinting in that way they do when she has a plan.

Again, for probably the dozenth time tonight, what is she even talking about? Don’t pretend. Then we’re back to the original issue of not being confident.

“Robin, what do you even mean?” He asks, his voice sounding somewhat hopeless even to his own ears.

But Robin doesn’t seem to mind all that much, she just grins a little wider and says, “Pretend you’re someone else.”

Someone else. So like, pretending, but different. That’s still pretending though.

“Pretend you’re like, I dunno, a super flirty hot guy from some 90’s movie, and go hit on that guy till he’s gone all red.” She breaths, lowering her voice, but speaking with just as much, if not more fervor.

Will can’t help but let out a little chuckle, rolling his eyes at her. Always one for the descriptions.

“Or,” she goes on, and Will can tell if she doesn’t stop soon it’ll turn into a full blown ramble.

“Pretend you’re somebody you know, like, uhh, Max!” She says, snapping her fingers loud and clear about an inch from Will’s face as she grasps her idea.

Max. Pretend to be Max. Well then he’d scare the guy off with bitchiness.

“Robin-“ he begins to argue, exasperation thick In his voice, because honestly, what is she talking about?

“Just, try it, okay?” She pleads, even going the extra mile and clasping her hands into a praying gesture at him. Puppy dog eyes glinting up at him and everything.

Will’s arms move instinctively into a tight cross over his chest, a frown spreading over in a lightning strike of unhappy wrinkles across the lower half of his face.

She can’t be pulling this on him. Just try it.

I’ll try. That’s what he had said to Max. A simple, impossible statement. An empty promise.

But it doesn’t have to be empty. The sly and betraying voice urges.

What’s there to lose? It asks. Stupidly, patronizingly.

What’s there to lose? Gee, who knows, his job, his dignity, and any semblance of self respect.

You wouldn’t get fired. What will the manager mind if you bat your eyelashes a bit? That’s Robin talking, the responsible voice argues.

But really, maybe if he just tried…

And it’s not like lost dignity is new. Well that’s true enough.

 

Fuck it.

“I’ll do it.” Is what he says, in a voice that doesn’t quite sound like his own, letting the words that he will surely regret later, fall out of his mouth.

Robin positively glows.

When Will had said “I’ll do it.” He had meant- well he’s not really sure what he’d meant, but it wasn’t this.

It wasn’t going back to get 7b (who were apparently the Wheelers as signed over their check) and keeping his eyes off the boy.

Talk to him after his family's gone, is what his head urged, indistinguishable which of the voices it was, the one that acted like a little cartoon devil on his shoulder, or the angel.

The only problem with this brilliant plan of his, (one that he hatched as a somewhat compromise with Robin’s help, because he’d said “There’s no way I’m asking out a guy in front of his entire family.”, was the interaction in the center of the two objectives.

Those being, get the check, and talk to him while his family gets ready. Whether that consists of a “Wanna maybe get coffee sometime?” Or something Infinitely more embarrassing and fueled by nervousness.

His plan was going fine, a thought that brings a twitch downwards of his lips, as it makes him feel like he’s in Ocean’s 11.

But, his plan was going fine, until-

SMACK

“Woah, sorry!” Will yelps on reflex, clumsily taking a step back from the hurtling force that had just collided head on with him, and lifting protective hands towards the form ahead of him.

The tall, pale, and freckled form.

Does this count as Murphy’s law? Or is it just Will Byer’s Extremely Shitty Luck ™ that he of course has to collide with this guy?

The man across from him gapes, like, actually gapes. Mouth wide in a little, surprised “o”, as a flush spreads across his features, giving him a softer look across his sharp face.

It’s pretty.

Not the time. This is the time, actually. The perfect time. Oh yeah. Then better to get the character ready.

The character that isn't afraid of this, isn’t scared of rejection or flirting, and hasn’t been avoiding this. No, he seeks it out.

Steel yourself, you can be an actor. High school plays count.

Will clears his throat in a way he hopes isn’t as awkward as it sounds through his own ears, before asking

“Hey, you okay?” He draws out the question, letting his syllables stretch, cutting them off just short of breaking. That’s how people with flirty voices do it in movies. A voice that sounds more like Dustin than Will’s ever conjured up before says.

He doesn’t really look okay, with his mouth still open and eyes wide and unanswering, but Will can’t exactly focus on that because he’s too busy seeing just how tall this guy is.

He could imagine just fine while the man was sitting. His legs are long and bony, that’s obvious, even when they’re crossed under the table, or bouncing, but, this guy is tall.

“Could you help me win a bet?” He spits out the words like fire, tumbling over one another in a terrible hurry to get them out and in turn, ruin Will’s perfect two step plan.

Well this just seems like an asshole frat guy then. “Can you help me win a bet?” Which seems code enough for “I dare you to go tell that guy you like him.” And cruel laughing as the end result.

Play along, practice. Practice doesn’t work on some joking prick. Who says he’s joking?

Pretend you’re Max. But nicer. Max but nicer, he can do that.

“What kind of bet?” He asks, the path between his brain and mouth blurring, the once clear path overgrown by thorns and bushes.

The guy’s face goes slack, eyes wide in an overly panicked way that Will should not find pretty.

“I-What?” The guy sputters, hands fidgeting nervously along his sides.

Yeah, feel that. No, you don’t.

Will has to suppress a bubbling giggle, so startlingly unlike him that he almost laughs fully.

This is not how Will Byers reacts to something stressful and vulnerable, Will Byers fidgets, and stutters, and second guesses himself. He doesn’t giggle at the cute guy as he learns to flirt like breathing.

And it strikes him simply, calmly, like the sea's tide sweeping over the sand, that this is easy. Admiring this awkward, lanky man, and letting his eyes drift in a way that blurs between mildly suggestive and polite in a way Will didn’t think anything could.

This is sort of fun. There’s a twinge of anxiety stored away in the back of his head telling him that he should be stressed right now, but he isn’t really.

With this new revelation fueling him like gasoline to a crackling fire, Will smiles brighter at the man, and lets his mouth move without thinking too hard first.

“What kind of a bet is it you need my help with?”
Will asks, words smooth and even.

The guy's face falters, lips stilling from where he’d gotten to biting at them, seemingly unknowingly, eyes going even wider, if that’s even possible.

Pause.

“No- it’s, nothing. Nothing! I shouldn’t have- I’m sorry.” The guy bursts out, eyes darting about the room, finding anything to look at that isn’t Will.

“No, really. Tell me.” The words come easily now for reasons he can’t comprehend, his brain whispering that this shouldn’t be this easy.

The guy’s head snaps up fast enough that Will wouldn’t be surprised if it snapped in two.

“I really shouldn’t-“ the guy backtracks, guilt thick in his voice as he wrings his hands together. Hopefully not guilty for being a frat dickwad, although, frat guys are never guilty.

He’s so nervous that it’s cute.

“C’mon, just tell me. I’m far too invested now.” Will drawls, his insides screaming muffled gasps of shock as he sinks into character.

You can see the exact moment the words strike the man, any passerby or people watcher could pinpoint the moment that whatever words might’ve been said, hit the man with the curly hair.

The watchers would think Okay, so either the brunette just flirted with him, or the curly haired guy is having a stroke.

“Far too invested? What do you-“ the guy stammers, voice pitching higher and squeakier as his cheeks grow brighter pink in the dim lights.

The poor guy really does look like he could be having a medical crisis of some kind, and there’s really no need to torture him.

So Will takes pity on him, and says, “But really,” what kind of a bet?” Leaning against the cool cashier counter, and thoroughly ignoring the reminder of what he should be doing right now to keep his job.

“Maybe I’ll help.” The ‘If you’re not going to laugh me out of town with your frat friends (mostly overruled option saying as the guy can barely speak without apologizing and blushing) or kidnap and murder me.’ part goes unsaid.

Besides, this is strictly practice. Even though he chose a very hot guy to practice flirting on, it’s still just practice.

For all Will knows, the reason this guy is so stammery and blushy is because he’s a straight guy getting hit on by another guy.

But Will’s gotta get practice in somehow.

“My sister bet me that I can’t get a date for her birthday party in under two weeks.”

Oh, well, that’s quite the bet.

Why would such a straight guy want a date with a guy? That would ruin his rich looking parents’ whole big family facade. Gay sons don’t fit into the ideal suburban family.

So, the only logical reason he’s picked Will for this, is because he wants to piss them off.

A bet that he wants Will’s help with. A date. With Will.

That’s the end goal when you flirt, idiot.

But only to make his parents mad, probably.

“I’ll think about it.” Will manages, voice sounding too far away. But it’s worth it to see the guy’s face light up the way it does. The way his eyes brighten, his eyebrows shoot up, and he looks like the most anxiety riddled person to ever win the lottery.

A date, him and me, on a date. For a bet. But, still. A pretend date with a stranger.

Will’s searching his apron pocket for anything vaguely papery before he can think much of it. He’ll need a phone number to find me, he thinks numbly, as his hands roam of their own accord.

Finally coming across something crinkling at the tips of his fingers, Will pulls out what happens to be the Wheeler’s receipt, before he fishes out his pen along with it.

Flipping the receipt, Will steals himself like a teenager about to tag a stop sign four feet away from a cop, (though he’s not entirely sure why he feels like he’s vandalizing school property and not giving some guy his number) and clicks the pen open. Scribbling his number down in the blotting green ink as quickly as he can.

“Here’s my number. I’ll need more details, like who you are, and if you’ll like, kill me or something.” Will mumbles, smiling nervously at the man across from him, the man who still stands just as speechless as before.

Mouth hanging just a little open, and eyebrows drawn like he’s beyond confused, but not complaining.

“Anyways,” Will manages, swallowing dryly, “call me.” He finishes his writing clumsily, smiling as normally as he can, and pretending he can’t feel his lips pull taught across his teeth, how unnatural it feels, as the adrenaline apparently melts off and the creeping anxiety takes hold.

The guy doesn’t seem to have noticed though, Will’s growing panic or the fact that he’s holding out his number for him to grab.

“Hello?”

The guy blinks quickly, seemingly waking from whatever trance he was in with a start.“Yeah?” He squeaks out.

“I- thanks. Yeah, thank you.” The guy finally says, reaching out for the inked check with shaky movements that Will has the manners to pretend not to notice.

Yeah, practice’s over, time to go.

Turning in a way that he hopes doesn’t look as unsure and shaky as he feels, and he’s off towards the door.

Before, with one last drop of adrenaline-fueled energy strikes him like a bolt of spontaneous lightning, and he turns, smiling softly at the stunned man still clutching the receipt in one hand, as “And I’m Will.” Falls from his lips.

Before he’s swinging those doors shut behind him, leaving the speechless, jittery man standing there, holding Will’s number, and Will is off to the back of the kitchen to spill his guts to Robin.

Notes:

Also Portique is French for Swing-set (where Mike and Will met in kindergarten)

Thank you to Way_Back_In_July for saving me with the google translate idea!

Kudos and comments are always appreciated! (Your guys’ comments are so nice thank you so much!!)

Hope you liked this chapter!

Notes:

Mike is such a loser bro oh my lord.

Also, I made a playlist for this fic when I started writing it, so I can link that eventually if anyone cares and I can figure it out.

Also also, so when I pasted all this in it deleted the italics I put in, so just keep in mind they WERE THERE, I swear it, so if stuff isn’t italicized it probably should be, I only added some back in.

Hope you liked it! I’ll update when I can!