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Error 404, Chapter 1 Date Not Found

Sam Winchester x fem!Reader | WC: 8304

Summary: You’re Lucifer Morningstar’s personal assistant, so you’re used to putting out fires. Except for the ones in your own life. Your computer decides to take a sabbatical. And to make things worse, an upcoming business event requires you to bring a plus one. Fortunately for you, the solution to both problems might come in the form of a very tall, very pretty IT guy.

Tags/Warnings: Office AU, meet-cute, fake dating adjacent, fluff with feelings, romantic tension, reader is overworked and underpaid, no use of Y/N, no beta we die like men

A/N: Okay!! Kicking off this lovely Fic War put on by @mariekoukie6661! I’ve got one of my besties @roadhousearchives conspiring with (against?) me, and I’m excited to see how it goes! For the uninitiated, this is going to be a six-chapter work where @roadhousearchives and I alternate between chapters. I write the odd ones; they write the even ones. We each have our own prompt/storyline we are writing for, but we also have to adhere to everything the other has written. If it doesn’t make sense, trust me, it will as we go along.

The first sign that your day was going to be terrible came at 6:12 in the morning. Not because of the alarm, – it hadn’t even gone off yet – and not because of the rain that tapped steadily against your bedroom window. Hell, it wasn’t even because you had woken up with one arm tingling numb and the faint, suspicious ache in your neck that suggested you had slept on it wrong. No, the sign that your day was going to be awful was the text waiting on your phone.

Lucifer Morningstar: Need you in early.

You blinked, bleary-eyed and still half-asleep, at the screen. The message had come in at 5:48am. You stared at it for several long seconds, half-buried beneath your comforter, hair messy, and half your brain still clinging desperately to sleep. Your phone buzzed with another message.

Lucifer Morningstar: Also call Crowley. He’s being difficult.

You groaned, pulling the comforter over your head and setting your phone back on the bedside table.

“Good morning to you too,” you grumbled. For one beautiful, reckless second, you considered pretending you hadn’t seen it. You could roll over and go back to sleep and wake up at a reasonable hour like a normal person with a normal job and a normal boss who understood boundaries and the general concept that humans didn’t run off of caffeine and desperation. Then reality caught up.

Lucifer Morningstar did not understand boundaries.

Lucifer Morningstar understood power, image, money, and the particular brand of wealthy importance that made men in expensive suits believe that the universe was created to serve them. And you were his assistant.

Officially, your title was Executive Assistant to the Chief Executive Officer of Morningstar Industries. Unofficially, you were a calendar wrangler, crisis manager, interpreter of Lucifer’s vague commands, keeper of impossible passwords, buyer of emergency cufflinks, emotional shock absorber, and the person everyone found when something went wrong and they didn’t know who else to bother.

You sat up. Your neck protested, and you rolled it slowly, grimacing as it stubbornly refused to pop. Your phone buzzed again.

Lucifer Morningstar: Where are we with the Crowley file?

“We are in bed, Lucifer.” You scrubbed your hands over your face, groaning as you resigned yourself to an earlier-than-usual day. Sometimes, you questioned if your boss really was the devil like his namesake implied. But you were already pushing the blankets off of yourself and swinging your legs over the side of the bed.

By 6:37, you were in your car with your hair pulled back into something that technically qualified as professional, mascara in your purse for later, and a travel mug of coffee wedged into the cupholder like a life-support device.

By 6:58, you were walking through the lobby while answering a call from Crowley, who was, as Lucifer had promised, being difficult. You held up your employee badge to the security guard behind the desk, but you were pretty sure that Dean had every employee’s face memorized by now. There was a reason he was the lead security guard.

You ended the call as the elevator doors opened. The executive floor was already awake which was hardly a surprise. Morningstar Industries had never been the sort of place where people arrived. They appeared, fully formed, with laptops open and cold brew in hand, already annoyed by something.

“Thank God,” Jo Harvelle said the second she saw you. Jo was perched on the edge of your desk like she owned it, blonde hair pulled back, leather jacket on, and boots crossed at the ankle. She worked in events and donor relations, which meant she spent half of her life charming rich people and the other half threatening vendors who underestimated her because she looked sweet until she opened her mouth. This particular morning, she looked like she had witnessed a crime and was hoping someone would let her solve it with a shotgun.

“What happened? Why do you look like you’re about to ruin my morning?” You asked, eyeing her warily.

“Azazel is here.”

You swore under your breath. “Azazel’s not supposed to be here until Thursday.”

“I know.”

“It’s…” You checked your phone. “Tuesday.”

“I know.”

“Why is Azazel here?”

Jo gave you the look people gave bomb technicians when a suspicious package started ticking. “He says he has a meeting with Lucifer today.”

You closed your eyes and pinched your nose. Lucifer Morningstar, CEO, billionaire, menace, and a man who had never once understood that putting something in his own calendar did not automatically put it in yours. You’d shown him how to do that at least three separate times, but he never utilized the function.

“Is Lucifer here yet?”

“Nope,” she said, emphasizing the ‘p’ sound. You inhaled through your nose, held it for a moment, then exhaled.

“Okay.”

“You’re doing the voice,” Jo said as she watched you with open admiration and a hint of pity.

“What voice?”

“The one you use right before you fix something that shouldn’t be fixable by anyone less than Superwoman herself.” You adjusted your bag on your shoulder and took a sip from your travel mug.

“I need coffee.”

“You have coffee.”

“I need coffee that didn’t come from my kitchen while I was considering faking my own death.” Jo nodded and hopped off your desk.

“Cheap price for a miracle,” she said before making her way towards the elevators. You set your bag and coffee down at your desk and headed towards Conference Room B. Azazel was waiting inside with two aides, a leather portfolio, and the expression of a man who had never once been told to wait in his life. You smiled sweetly at him before he could speak.

“Mr. Azazel. I am so sorry for the confusion.” His eyes landed on you and narrowed dangerously.

“Confusion?”

“Lucifer’s previous meeting is running a little long.” A lie. Lucifer was probably still in his car, listening to music too loudly, and ignoring every call from Jo. “I know he was looking forward to speaking with you personally, but I don’t want to waste any of your time. I’ve arranged for breakfast to be brought up, and I can walk you through the revised projections while we wait.” One of Azazel’s aides looked relieved. Azazel did not.

“I was under the impression that this was a private conversation.”

“Of course,” you said in a tone that suggested you had everything under control. “And it will be. I’ll just make sure the materials are ready for him.” Azazel studied you, and you held his gaze with pleasant, professional emptiness. You’d dealt with powerful business men long enough to perfect ‘the look.’ After a moment, he sat down.

“I take my coffee black.”

“It’s already on its way.” It was not. You stepped out of the room and immediately grabbed the nearest junior assistant. “Call downstairs. Three coffees. One black, one oat milk latte, and one… uh, get whatever’s expensive on the menu. And pastries. Not muffins. Azazel hates muffins.” The assistant blinked at you, wide-eyed.

“H-how do you know that?”

“Because last year he called them bread without ambition.”

You were already moving again. At your desk, your computer woke slowly, and your inbox already had eighty-three unread emails. Thankfully, nine of those were from idiots who didn’t understand that they didn’t need to use the ‘reply all’ function for birthday wishes. Your calendar was a solid wall of color. You plopped down into your chair and cracked your knuckles before logging into your computer and steeling yourself for the day.

You opened the Crowley file, found the Azazel projections, texted Lucifer no less than six times that Azazel was two days early, accepted two meetings, declined one, moved another, pulled up the seating chart you’d been fixing to have Lucifer review it, and still somehow managed to answer a call from the legal department all before 7:30.

At 7:34, Lucifer Morningstar finally arrived.

He swept onto the floor in a black suit that cost more than your rent, sunglasses on despite being indoors, and an expression bright with the kind of cheer that meant someone else was about to suffer. He pointed at you. You pointed at Conference Room B. He frowned, and you mouthed, Azazel.

“Why is Azazel here?” His expression fell. To his credit, it was barely noticeable. To your credit, you didn’t throw your coffee at him.

“You invited him.”

“I invited him for Thursday.”

“You invited him for today.”

“I told you?” He strode towards you, pushing his sunglasses up to the top of his head.

“You told Outlook.” You pulled up the calendar and tapped on the colored blockout labeled ‘Azazel meeting.’ Lucifer grimaced like Outlook had personally betrayed him. You handed him a folder. “Breakfast is in the room. He’s been waiting for twenty minutes and thinks your previous meeting ran long. The projections are flagged. Avoid page seven unless he brings up distribution. If he does, just say we’re exploring options.” Lucifer took the folder, already opening it and skimming over the pages.

“Right.” He turned towards the conference room before pausing. His mouth curved, charming and lethal as he glanced over his shoulder back at you. “What would I do without you?”

“Crash and burn.”

“Ah.” He smiled wider. “But beautifully.” Then, he disappeared behind the glass door. Jo appeared beside your desk with a paper cup from the good coffee place two blocks away. You stared at it like she had brought you a gift from God himself.

“Ugh, I love you.”

“Yeah, yeah. Don’t make it weird.” You took the cup from her, reveling in the smell of a drink you didn’t have to fix for yourself. “Does Azazel really hate muffins?”

“Deeply.”

“And you remember something like that?”

“I remember everything that can be weaponized.”

Jo lifted her own coffee in a toast. “That’s why you’re terrifying.”

“I prefer the term indispensable.”

The rest of the morning dissolved into a blur of phone calls, scheduling disasters, and executive hand-holding. You were halfway through typing ‘DO NOT MISS THIS’ on one of the meetings you had added to Lucifer’s calendar when your computer screen flickered. You went very still. “No, don’t do this,” you warned. The screen flickered a second and then a third time. The cursor stopped blinking. Your calendar froze. A tiny spinning wheel appeared where your mouse should’ve been. “No, no, no, no.”

You clicked. Nothing happened. You wiggled the mouse and clicked again. The spinning wheel continued spinning. You leaned back in your chair, staring at the screen as if it personally had insulted the entirety of your bloodline. Jo passed behind you and stopped.

“What’s wrong?”

“My computer’s considering a mutiny.”

“Did you save the seating chart?”

Your stomach dropped. The gala seating chart. The version you had spent two hours fixing the previous night because Lucifer had decided that the governor couldn’t sit near the head of the board because of “vibes.” You hated when he tried to use modern day slang. He was far too old for it. You clicked frantically. The computer made a noise that didn’t sound reassuring. It was a small, hopeless chirp. Jo winced.

“That didn’t sound good…”

“I swear to God, if this thing dies, I’m walking into oncoming traffic.”

“Please don’t do that. Lucifer would make me do your job.” You picked up your desk phone and called IT. The line rang twice.

“IT, this is Sam.” You barely registered the voice. Male, calm, a little tired maybe. Pleasant in a way that you currently didn’t have the bandwidth to appreciate.

“My computer froze and made a weird noise.”

“What kind of noise?”

“The kind that suggests that it wants its last rites.” There was a brief pause. Then,

“Okay, let’s not administer those yet.”

“I’ve got a seating chart, a board retreat, three contract revisions, and a CEO with the technological instincts of a haunted Victorian child. I need this computer to stay alive.”

“I understand.” He sounded like he did, and that annoyed you slightly. No one should sound that calm while your life was hanging off a precipice. “What’s your name?” he asked. You gave it. There was typing on the other end. “And you’re on the thirty-ninth floor?”

“Yes.”

“Okay. I’m going to remote in, if it’ll let me. Don’t click anything.” You looked down at your mouse. Your hand was already on it. The cursor moved on its own. You pulled your hand away from the mouse.

“Oh good, now it’s possessed.”

“That’s just me. Told you I was gonna try and remote in.”

“Are all IT issues solved through demonic possession?”

“Only the stubborn ones.” You took an extra second to process his words before you huffed a laugh despite your situation. Sam clicked through several windows while you watched helplessly. The computer stuttered, and the fan kicked on. Your email flickered back to life for half a second before freezing again. “That’s not ideal,” Sam muttered under his breath.

“Please don’t say that.”

“Well it’s not catastrophic, at least.”

“Somehow that’s worse.”

“It’s just your system choking on a sync error.”

“Well that’s something me and my computer share in common,” you grumbled. If Sam heard you, he didn’t say anything about your comment.

“I can stabilize it enough for now, but I’ll probably need to come upstairs later and take a closer look.”

“Later is fine,” you said immediately because three people were now hovering near your desk and Lucifer had just opened his office door like he could smell the delay. “I just need it to survive the next few hours.”

“I can do survival.”

“Great. Survival is all I’m aspiring for right now.” He gave a quiet laugh. It was low and warm, and if your life had been even ten percent less on fire, you might’ve noticed it properly. Instead, Lucifer called your name from his office. You covered the phone. “One second.”

“I need the revised Crowley file,” Lucifer said.

“Crowley sent notes?”

“No, but I need the file.”

“Why?”

“So I have it.”

“It’s–” you started then cut yourself off, staring at him in disbelief. You had placed those files in the shared drive. He had them. Lucifer stared back at you, expression completely serious. You uncovered the phone. “Sam, how alive are we?”

“Alive enough to email a file.” You could practically hear the smile in his voice. Covering the phone hadn’t been enough to hide your conversation.

“Beautiful.” You sent Lucifer the file he absolutely had already. Sam did something else on the computer, and the fan quieted.

“There. That should hold for now,” he said. “Don’t restart it.”

“Got it.”

“And,” Sam said your name, “your forty-seven open tabs aren’t helping.” You looked at your browser. “I’d limit yourself to five until I can figure this problem out.”

“I feel like you’re judging me.”

“Just a little.”

“Fine,” you relented, clicking through them. “I’ll try to limit myself.” Lucifer called your name again, and you sighed, pinching the bridge of your nose. “Thank you, Sam from IT.”

“Anytime.”

You hung up and immediately forgot the call. Not because he had been forgettable, but because the rest of the day swallowed him whole. The afternoon came at you with teeth. A set of notes for a new deal came in at 12:56 which meant that Lucifer wanted them summarized by one.

At 1:14, a board member’s assistant emailed to ask whether spouses were invited to the annual Morningstar Foundation Gala.

At 1:15 you remembered the gala existed.

At 1:16, your headache sharpened into someone hammering an ice pick into your skull.

The Morningstar Foundation Gala wasn’t a simple corporate event. It was a ritual sacrifice performed annually in formalwear. Every year, Morningstar Industries rented out an obscenely expensive venue, invited half the city’s elite, and raised enough money for a cause Lucifer cared about just enough to mention in interviews. The photos that made everyone involved look generous and deeply invested in community outreach didn’t hurt either. And everything was dialed up to eleven this year in particular because Lucifer was in the midst of courting the Novak Group who had ties to some very, very old money.

Every year, you coordinated almost all of it on your own because Jo would walk out if she had to cater to every one of Lucifer’s whims. Every year, you vowed you would quit before the next one. And every year, you still, somehow, remained employed. You navigated to the gala folder on the shared drive, and your computer thought about freezing again.

“Don’t you dare,” you whispered. It obeyed, but only just. The folder contained subfolders for everything that you would need, all of them sorted and easy to navigate. You’d threatened bodily harm to anyone who messed with your system. There was a new file that wasn’t placed in any of the subfolders and simply titled URGENT PLEASE READ. You clicked on it. It was a memo from communications. You read it, rubbed your eyes, then read it a second time.

Absolutely not.

“What?” Jo looked up from her desk, and you realized that you had spoken aloud. You didn’t answer her and simply read the message again.

Due to the high-profile nature of this year’s gala and expanded press attendance, all executive staff and senior support personnel are expected to attend in formal capacity. Plus-ones are strongly encouraged to maintain the event’s relationship-forward optics.

Relationship-forward optics. Which was just corporate speak for ‘we’d like to give the illusion that all of our employees are stable.’ Jo appeared beside you and read over your shoulder.

“Oh...”

“Don’t say it like that,” you said with a sigh.

“Plus-ones strongly encouraged.”

“I can read.”

“Senior support personnel means you.” Jo took on a sing-song sort of tone. “Do you have a plus-one?” You looked at her, deadpanned. She winced. “Right... sorry.”

It wasn’t that you couldn’t get a date. You absolutely could. Probably. In theory. It was simply the fact that you didn’t have the time to find one. Dating required free evenings and the ability to answer texts in less than three to five business days. You didn’t have either of those. Your last attempt at dating had ended after a guy named Eric told you that he felt like he was “competing with your calendar.” Which was a ridiculous notion. He hadn’t been competing. He had lost. Immediately.

“I’m going to be working the entire night. There’s no point in bringing anyone,” you said, shaking your head. Jo made a face.

“I don’t think you’re gonna get a choice.”

“There’s always a choice.”

“Not with Lucifer.”

And unfortunately, she was right. Lucifer cared about optics the way other people cared about oxygen. If communications had decided that plus-ones mattered, then Lucifer would decide that your visible personal life was suddenly part of your job description. Speaking of the devil... Your computer pinged. A new email from Lucifer.

Gala Attendance

You stared at it, mentally cursing him back to the deepest pit of Hell you were sure he crawled out of. Jo backed away slowly.

“Coward,” you muttered.

“Survivor,” she corrected cheerfully, disappearing behind her desk partition. You opened the email to find a single line.

Need you to account for yourself and your plus-one in the seating chart.

You barked a dry laugh, only because the alternative was screaming, and hit the reply button before you could properly formulate a solid excuse. Frankly, you didn’t have one. Lucifer wouldn’t accept ‘I couldn’t find a date,’ and the chances of bumping into some magically perfect stranger at a coffee shop were slim-to-none. Mainly because it would require you to go to a coffee shop. Which required free time. Your cursor blinked in an empty draft, taunting you.

Who did people bring to things like this? Friends? You had friends. Most of them knew better than to attend a corporate gala, though. Exes? You’d rather eat glass. A hired escort? Tempting, but you weren’t sure you wanted to deal with that expense just for an appearance. You scrolled through the contact list on your phone, despair rising with every passing name. Jo leaned over the desk partition.

“Lemme guess: he’s not giving you a choice,” she said, picking at her nails. You groaned and let your phone fall onto your desk with a heavy thud. “What about that guy you went out with? Graham? Eric?”

“I’d rather bring the emotional-support peacock Gabriel put in the charity auction last year.”

“Fair enough.”

“You got a cousin who’s available next weekend and wants free food? All they have to do is wear a suit and hold a thirty second conversation with Lucifer.”

Jo raised an eyebrow. “All my cousins are either married, criminals, or both.” You sighed. Jo took a sip of her coffee. “What about Dean?”

“The security guard?”

Jo nodded. “Yeah, he’s hot, and I’m sure he cleans up real nice.”

You shook your head. “I’m pretty sure he’s gonna be working, and I doubt Lucifer’s gonna let me off the hook that easily. Yeah, I’m totally here with the security guard. So what if he was going to attend anyway.”

Jo hummed thoughtfully, spinning in her chair. “What about the IT guy you talked to? He seems like he can hold a decent conversation.”

“Jo,” you said, giving her the most stern expression you could muster. “The company employee list isn’t a dating pool. Also – not that it matters because I’m not asking him – I don’t even know what he looks like.”

“It’s not like you have to be attracted to him. You’re not asking him to marry you,” she said, rolling her eyes at you. “You’re asking him to wear a suit and stand next to you while he enjoys a shrimp cocktail.”

“It’s fine, Jo. I’ll get it figured out.”

“You always do.”

And that was the problem. Everyone believed it. If there was a fire, you found water. You handled all of it. You were good at being useful. Excellent at being needed. But you weren’t sure you remembered how to be anything else anymore.

By three o’ clock, the day had reached the point where time stopped behaving normally. Minutes stretched and collapsed. Emails blurred together, and you answered them without remembering opening them. You had to revise the seating chart again because the head of development had neglected to mention that two donors were in the middle of a divorce so vicious that it had its own nickname, and you received no less than three text messages from friends that you didn’t answer because all of them began with some variation of “are you alive?” It was a completely valid question. You weren’t sure anymore.

At 3:26, Jo rolled over to you with a bag of chips in hand. She dropped them onto your desk wordlessly, and you opened them, eating three without looking away from your computer. As you hit the ‘new tab’ button in your browser, putting you at six tabs beyond your allotted five, the screen stuttered again. You glared daggers and pointed a chip at it. Jo immediately rolled away.

“I definitely don’t want to be here for this.” She gave a low whistle.

“Coward.”

“Survivor,” came her sing-song response. You picked up your phone.

“IT, this is Sam.”

“You have thirty seconds to talk me off a ledge.”

“You went over five tabs, didn’t you?”

“I needed those tabs, Sam,” you argued. There was a sigh on the other end of the phone, and you did not have the patience to deal with admonishment from the IT guy.

“Okay, well I’m actually just about to head up there.”

“Oh.” You weren’t expecting that.

“Yeah, finished up with the server. I’ll be there in five.”

“Great. Yeah, uh… thanks. I’ll try not to threaten it until you get here.”

You hung up the phone and slumped in your chair. Then you sat up, just a little straighter. Not because you cared, obviously. But you were about to meet the person who had saved your career. It was completely normal to want to look like you hadn’t been assembled from caffeine, panic, and dry shampoo. You glanced at your reflection in the dark screen of your monitor. You weren’t a total disaster, at least. Your thoughts drifted to the mascara sitting in your bag before immediately dismissing the thought. You were not putting mascara on for IT.

Your phone rang, and you grabbed it in the middle of the second ring. It was legal, going on about sending over several documents that needed Lucifer’s signatures. In the midst of the call, your cell pinged with three new emails, and Lucifer sent you a text that just read Novak seating? You were vaguely aware of someone standing at the edge of your desk, but they were going to have to wait because you were in the middle of trying not to tear your hair out.

“Give me one second,” you said, holding a finger up as you tapped out a response to Lucifer on your phone.

“No problem.”

The voice was familiar, warmer in person than it had been on the phone. You kept typing for half a second before your brain caught up and processed where you had heard the voice before. You looked up and had the strange, disorienting experience of realizing that Sam from IT was tall. Absurdly tall.

He stood on the other side of your desk with a laptop bag slung over one shoulder and a small toolkit in hand. His employee badge was clipped to his belt. Sam Winchester, IT Department. His brown hair fell loose around his face, just a little too long to be corporate approved, and his navy blue polo was tucked into the waistband of his slacks. And as your eyes finally landed on his face, you’re pretty sure your jaw went slack.

“Oh,” you squeaked. Sam’s eyebrows rose slightly, and he lifted his free hand in greeting. “You’re Sam.”

“That’s me.”

“From IT.”

“That too.” You nodded once, like he was giving you a quarterly report rather than an awkward introduction – if it could be considered that.

“Right.” You cleared your throat. “Yes. Good. Uh... hello.” Jo made a small noise from her desk as she ducked behind the partition again, and if you could’ve done it without Sam seeing, you would’ve flipped her off. Sam’s mouth curved into something that wasn’t quite a full smile but was still somehow worse. It was something subtle.

“Thirty-nine?” he asked, looking at the overpriced paperweight on your desk.

“Yup.” You gestured towards your computer with as much dignity as you could cobble together. “She’s being dramatic.”

“Sounds like you two have a complicated relationship.”

“Our counseling session is on Friday.” Sam set his bag down and stepped around your desk. You moved your chair back to give him room, and he leaned down to boot up your computer and type on the keyboard. He smelled clean, like laundry detergent and rain and something warmer underneath it all. You pursed your lips together, cursing yourself for noticing. His hands moved over the keys with practiced ease. They were impossibly large. Everything about him up close was impossibly large. And absolutely none of your business.

When you were sure Sam was sufficiently distracted by your computer, you shot a glare towards Jo. She was watching over the top of her monitor with the expression of someone who was witnessing a workplace incident she had every intention of dissecting later on. You narrowed your eyes at her as her gaze darted from you to Sam and back to you again. She gestured at Sam and gave you a meaningful look. You flipped her off, and she ducked down. Coward. Survivor, you heard Jo’s voice in your head.

“So...” you began, ignoring Jo out of the corner of your eye. “Is she saveable?”

"I wouldn't put a funeral on the books for her just yet," he murmured. A line of code ran across the screen followed by another. "But she's definitely got something going on."

"Lovely..."

He typed some more, and the computer whirred in protest. "It looks like it's some sort of sync error that's trying to pull multiple instances of your drive at once," he said after a moment. You nodded. Separately, you understood each of those words, but in that specific order, you weren't completely sure what in the world any of it meant. "It's probably a result of the last security patch. Nothing that a deep dive and full restart won't fix."

"So... you're saying you can fix it?" He nodded and made an affirmative sound without looking at you. "You are a Godsend, Sam." Your shoulders loosened.

"Don't worry about it. It’s what I do.” Sam straightened up and leaned back, giving you a chance to get a better look at his face. His eyes were soft, and he offered you a faint smile. “I just need to reboot it. She’s gonna take a few minutes to come back up because she’ll need to reallocate some things.”

“So… I need to find something to occupy myself with for the next few minutes?” you asked, glancing around your desk. There was a stack of unread memos, a half-eaten bag of chips, and your phone buzzing with, yet another, notification. Sam chuckled.

“Unless you want to watch a loading screen for five to ten minutes, yeah.”

You grabbed your phone and scrolled through your notifications. Three new emails, a message from Lucifer asking for the Novak seating arrangements, and a text from Jo that just said, he’s cute with a winking emoji.

“I’ve got some emails I can handle before my computer comes back online,” you said, glancing between your phone and Sam as you typed out a rather unprofessional response to Jo. Sam nodded, already turning his attention back to your computer.

“Go ahead. I’ll let you know when she’s ready.”

You stood and offered him your chair, taking advantage of the moment to stretch your legs a bit. After making sure that Jo wasn’t sneaking peeks over your desk divider, you let yourself steal a moment to admire Sam.

His jawline was sharp, and you couldn’t help but think that he wasn’t exactly the IT type. Admittedly, you might’ve had a certain stereotype of IT guys in your head, and Sam Winchester was definitely not fitting that mold. He looked more like he should’ve been modeling for some kind of underwear brand or a fitness magazine. You mentally smacked yourself and dragged your attention to your emails. You were halfway through responding to Lucifer’s request for the seating chart again with a response that wouldn’t get you fired when you vaguely registered Sam saying something.

“I’m sorry, what?” You looked up from your phone. Sam smiled at you, and you noticed a dimple in his left cheek that had no right being as distracting as it was.

“I said, you look like you’ve had a long day, and it’s only three-thirty.” His eyes crinkled at the corners when he smiled. You laughed, surprising yourself with how genuine it came out.

“Is it that obvious?”

“Only to someone who’s had days like that before,” he said, leaning back in your chair and crossing his arms over his chest. “The IT department’s pretty much the island of misfit toys for the company’s technology problems.”

“Then what does that make you?” you asked, setting your phone down and leaning against your desk. A playful glint flashed behind Sam’s eyes.

“The tinkerer that fixes it all.”

You smiled despite yourself. “Well I’m glad someone around here knows what they’re doing.”

“From what I’ve heard, you’re not exactly incompetent yourself.” His gaze flicked to yours, warm and amused.

“Oh?” You quirked an eyebrow, grin widening. “And what have you heard about me?”

“Word travels fast when someone can make Azazel wait without getting fired.”

“I just know how to handle difficult people,” you said, trying not to sound too proud while simultaneously ignoring the way heat rose to your cheeks.

“I’d say that’s an understatement.”

Your computer played its startup sound, and he turned to take a look at it. The screen blinked to life, the login screen appearing like nothing had ever gone wrong. Sam stood up from your chair and offered it back to you, and you were acutely aware of the height difference between the two of you as you settled down into it. “There we go. She should be good now, but I’d recommend taking it easy on the tabs until I can go in and do a deep scan after hours. Maybe limit yourself to, I don’t know, ten instead of forty-seven?”

You rolled your eyes at him, but there was no heat behind it. “I’ll try my best.”

“She and I would appreciate it,” he said, gesturing to your computer. You chuckled and shook your head at him.

“Okay, okay,” you acquiesced. “Thanks again for coming up here.”

Sam paused, slinging his laptop bag over his shoulder. “No problem. It’s always nice to get away from the server room.” He smiled at you again. “Those fluorescent lights can do things to a person.”

“Tell me about it,” you said, glancing up at the overhead lights. “I’m pretty sure the lighting here is designed to slowly drain the life from us all.” Sam laughed.

“Maybe we should start up a support group. Victims of corporate lighting.”

“Sign me up,” you said. You couldn’t think of a time you had smiled this much while at work. People didn’t usually smile while putting fires out. It occurred to you that he hadn’t moved to leave yet which was strange because most IT people tended to fix the problem then vanish like a ghost. Yet another thing about Sam that set him apart from most IT stereotypes.

“So,” he began, “anything else I can help with while I’m here?”

“Not unless you happen to have a buddy who wants to attend a stuffy corporate gala with me next weekend,” you said before you could stop yourself. Sam blinked, and you were pretty sure all the blood drained away from your face. Why did you just say that? Maybe Jo was rubbing off on you. That definitely had to come to a stop. ASAP. “That, uh, that came out wrong. I didn’t mean– I’m just stressed about work.”

Sam tilted his head slightly, studying you with those warm eyes that suddenly seemed more interested than they should’ve been. “The Morningstar Foundation Gala?” he asked.

“Yeah,” you said, feeling your face grow warmer. Your traitorous tongue kept going. “It’s this stupid corporate event where we parade around in expensive clothes and pretend we care about charity.”

“That sounds... interesting,” Sam said, his mouth quirking up. You backpedaled, realizing how bad it sounded.

“It’s not terrible or anything,” you insisted. “It’s just–”

“Stressful,” he finished for you. You nodded, thankful that he was giving you the space to recover from your slip-up.

“Stressful is an understatement. It’s like trying to organize a military operation with more egos.”

Sam laughed. It was a nice sound. Warm and genuine, and it occurred to you that you wouldn’t mind hearing more of it. “I can imagine. The IT department always gets requests about it. People suddenly realize that their tech doesn’t work just days before big events.”

“Ugh, story of my life,” you groaned. “Last year, we had a projector fail during the keynote speech. I had to find a replacement in under twenty minutes while wearing heels.” You shook your head. “And this year, they’ve decided that all senior support personnel need to bring a plus-one to maintain ‘relationship-forward optics.’”

“That sounds like an extremely corporate way of saying ‘make sure you look like you have a life outside of work.’”

A fresh wave of embarrassment crested over you. Why were you still talking about this? You should’ve shut up about the gala four sentences ago. You reached for your phone, feigning looking at a notification that didn’t exist.

“Yeah, exactly,” you murmured. Your face was unbearably warm, but you couldn’t bring yourself to be rude and shut him out completely. “It’s ridiculous." Sam nodded, shifting his weight from one foot to the other.

“Well, if you need any IT support during the event, just ask for Kevin. He’s the department lead, and he’ll be there.”

“Oh, that’s good to know,” you said, looking up at Sam and nodding just a little too enthusiastically. You tempered your reaction. “Kevin. Right. I’ll remember that.” Your eyes drifted away from Sam’s face, distinctly aware of the awkward silence stretching between you. Sam’s eyes were still on you, and you were suddenly very conscious of the chip crumbs on your desk and the mascara that you absolutely should’ve applied earlier on.

“Well,” Sam said, adjusting his laptop bag. “I should let you get back to work. Your computer should be good for now, but if anything else happens, just call down. I’ll leave my extension so you can reach me directly since I know what’s going on with it.” He grabbed one of your scattered pads of post-it notes and scrawled his name and extension down. “Just, uh... just in case.”

“Thanks,” you managed, taking the post-it note from him. “I’ll probably need it.”

“Well if I did my job right, you shouldn’t.” He flashed you a smile that was all dimples and teeth, and something unexpected fluttered in your stomach. “And good luck with the gala thing.”

“I’ll need it,” you repeated, completely professional. Sam turned to leave, and you watched him walk away, his tall frame disappearing around the corner. It was only then that you realized that you had been holding your breath. You exhaled slowly, looking down at the post-it note in your hand. Sam W. 0502 stared back up at you. His handwriting was unexpectedly neat for someone who spent most of his day typing. You stuck it to the corner of your monitor.

“Well that was smooth,” came Jo’s voice from behind her partition. You swiveled in your chair to find her peeking over at your desk, a knowing smirk on her lips.

“I don’t know what you’re talking about.”

“Oh please. That was the most awkward conversation I’ve ever witnessed.”

“I was just being polite,” you insisted, turning your attention to your emails as the program opened up.

“By blurting out that you needed a date?”

“I am under duress right now, Jo,” you hissed, burying your face in your hands. Through your fingers, you could see Jo’s smirk widen.

“Under duress? You were practically drooling over the IT guy. And he gave you his number! So that’s gotta mean something.”

“It’s his extension,” you muttered, tapping the post-it note. “For IT emergencies.”

“Right,” Jo said, drawing out the word with an exaggerated smirk. “IT emergencies. That’s what we’ll call them.”

“Jo–” you began, but she cut you off.

“He’s tall, he’s cute, he fixed your computer, and he can clearly hold a conversation for longer than thirty seconds. What’s the problem here?”

“The problem is that I don’t have time for this, Jo.” You hunched over your keyboard and began a response to one of your unread emails. “I have a seating chart to fix for the umpteenth time because my boss seems to think that ‘vibes’ are a legitimate concern.”

You could practically hear Jo roll her eyes. “All I’m saying is that you need a date, and he exists. This isn’t rocket science.” When you didn’t respond or look up from your screen, she huffed and dropped down behind the partition again. Sam’s extension sat innocently on your monitor for the rest of the work day.

Friday rolled around, and with it, the looming dread of the gala. You’d spent the week dodging Lucifer’s questions about your plus-one with the skill of a seasoned diplomat, but your time was running out. And while you were confident that you wouldn’t be fired over failing to find a proper date, Lucifer would tear into you for any perceived slight since the Novak Group partnership was on the line. That man could be terrifying when he was upset.

The post-it note was still stuck to your computer screen, taunting you day in and day out. You hadn’t spoken with Sam since he had come up to fix your computer beyond a single instant message exchange the following day when he followed up with how your computer was functioning. Work had kept you running around as per usual, but it hadn’t managed to push Sam from your mind. Thoughts of him lingered between tasks. The way he smiled. The dimple in his cheek. The warmth in his voice when he’d said your name. You found yourself glancing at his extension more often than you would ever admit.

As much as you loathed to hand it to her, Jo had a point. The finalized guest list was due at the end of the day, so the printing company could have everything going first thing on Monday. Every minute that ticked by was another grain of sand draining from your hourglass. Maybe you should just bite the bullet and call Sam. At least if he said no, then you could argue that you tried.

You glanced at the clock on your computer. It was just past noon. You weren’t sure of Sam’s lunch schedule, but he was likely already on it. You’d have to wait at least until one if you had any hope of him picking up…

As if on cue, your phone rang, and you practically leapt out of your chair like it had burned you. Had he–? Had Sam somehow–? You glanced at the caller ID, tempering your expectations when you realized that the call was coming from the lobby rather than the IT Department. You cleared your throat and answered.

“Hey, this is security downstairs. I’ve got a delivery for you, but the courier says it requires your signature. Looks like they’re program proofs.” You sat up straight and checked the tracking email. God, you had forgotten those were set to arrive today.

“Yeah, I’ll be right down.” You grabbed your badge.

The lobby was busy when you arrived, full of employees and visitors alike all participating in the quiet theater of corporate importance. Everyone moved like they had somewhere to be, even when they were just walking towards their next caffeine fix. You met the courier and signed for the proofs before accepting the large envelope and turning back towards the elevators.

And that’s when you saw him.

Sam was standing on the other side of the security desk, talking with Dean. He had his laptop bag over his shoulder and a paper cup in one hand. His hair was falling into his face as he glanced down at whatever Dean had set on the counter. You stopped walking, and the person behind you barely managed not to run into you, grumbling something as they brushed past you.

Sam looked up and caught your eye. Recognition moved across his face, followed by that warm, easy smile that had already carved itself a spot in your brain. He lifted his coffee cup in greeting. You should’ve nodded. You should’ve smiled and kept walking. You should’ve done literally anything normal. Instead, your legs had formed their own committee and voted against you.

“Sam from IT,” you said, mentally screaming at yourself because who the hell started a conversation like that? You could see the way Dean’s eyes sharpened with interest in your peripheral vision. Oh no, he was another Jo. Sam chuckled and said your name. God, why did it sound so nice when he said it?

“Staying under ten tabs?” he asked, and the playful tone in his voice made your stomach flip in a way that was entirely inappropriate for a Friday afternoon in a corporate lobby.

“Am I legally obligated to say ‘yes’?”

His cheeks dimpled. “Just tell me you’re not at forty-seven again.”

“I plead the fifth.” You clutched the envelope to your chest like it could protect you from all the embarrassment you were burying yourself under.

Sam shook his head, and you realized that you were staring at him like an idiot. “You’re a menace to your computer.” He turned his attention back to the device on the counter, picking it up and turning it over in his hand. “I’ll get this back to you when I’m done with it.” Dean made a vague noise of acknowledgement, eyes still darting between you and Sam.

You could practically see him assembling a theory in real-time, and this was the perfect point in time to make your exit. The conversation was short and sweet and didn’t need to be expanded on. You could wish them both a good day and head back to your desk. Instead, all you could do was stand there holding your envelope and thinking about your deadline.

Sam noticed your hesitation. “You okay?” he asked.

“You look like you’re about to negotiate with a hostage-taker,” Dean mused aloud, quirking an eyebrow up at you. He had the same conspiratorial kind of look on his face that Jo wore. You gripped the envelope tighter. It didn’t help that Sam was looking at you with genuine concern. Ask him. You could hear Jo’s voice in your head. Absolutely not. Ask him. No. Ask him, you coward. You were a survivor, not a coward.

“Do you own a suit?”

Sam blinked at you. You closed your eyes, begging to be struck down by whatever being was in higher power. It was the stupidest possible opening. Not ‘are you free next weekend?’ or ‘I have a weird favor to ask.’ No. Do you own a suit? You’d gone mad. Lucifer had driven you to actual insanity. When you opened your eyes, Sam was still looking at you, brow furrowed.

“I do,” he said after a moment.

“Great.”

“Is this an IT question?”

“No,” came your strangled response. “I’m asking for a totally normal reason.”

“Oh, this is awesome,” Dean guffawed, looking at you like you were the highlight of his day.

“Shut it, Win–” Oh fuck. “...chester.” Another horrible realization settled over you in an instant. Dean Winchester. Sam Winchester. You had just asked Sam out in the worst possible way in front of his goddamn brother. You’d rather risk Lucifer’s wrath over this.

Mercifully, Sam asked, “Is this about the gala?”

“Yes.” And you should’ve left it there. Yes was a complete sentence with no need to elaborate any further. Unfortunately for you, every fiber of your being was currently rejecting the notion of brevity. “It’s the gala. The plus-one situation I mentioned the other day.” The words tumbled out of your mouth. “I don’t have anyone to bring because I work constantly, and all the men in my contacts are walking red flags.”

Sam didn’t say anything. You continued because silence was lethal.

“And you fixed my computer, which isn’t a qualification, obviously, but you were calm and nice, and you didn’t seem horrified by my entire situation. And the person I ask needs to own a suit and hold a conversation, and you can clearly do both, unless the suit is a lie which would be really unfortunate at this point because I’ve already committed to the question. I’m going to stop talking now.”

Sam stared at you. You stared back. Your heart was pounding in your chest with the terrible force of a woman who had just made a simple question sound like a deposition.

“Sammy owns a suit,” Dean chimed in, looking like Christmas had come early for him. Sam gave him a look.

“You can say no,” you said.

“Sure, I’ll go,” Sam said at the same time. Your jaw went slack.

“Wait, you will?”

“Yeah.”

“Even though I’ll probably be working most of the time?”

Sam nodded, expression softening. “I’ve been to enough of these things to know how they work. I’ll be your charming accessory.” Your cheeks went warm, and you were pretty sure you were wrinkling the proofs in your hand.

But none of that mattered at the moment. Because you’d actually managed to find a date. A real, live, suit-owning, conversation-holding date who agreed to be your ‘charming accessory’ without a single ounce of pity in his voice.

“I, uh–” you squeaked before clearing your throat and trying again. “Thank you. Seriously. I promise I will find a way to make it worth your time.”

“Don’t worry about it,” he said, and you caught the faintest hint of a blush creeping up his neck. “Just text me the details, and I’ll be there.”

“I will,” you promised. Sam pulled his phone from the pocket of his slacks, and you couldn’t help but note that it looked comically small in his hands. He passed it over to you, and you typed your name and number into it, tamping down the giddy excitement fluttering in your chest. You handed it back to him. “I’ll text you the details. And the address. And the dress code. And probably a briefing on who to avoid.” You were already backing away before your mouth could betray you further.

“Looking forward to it.” Sam’s dimple reappeared on his cheek, and he typed out a quick message. You turned on your heel and made a beeline for the elevators, clutching the envelope to your chest like a shield. Your phone chimed on the ride up, and you let yourself smile like an idiot as you checked the notification.

Unknown number: Sam from IT. Suit confirmed.

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