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Jul 28, 2025

“Unexpected Upgrades” - Roy Kent x shy!reader

Summary: You meet Roy Kent at the airport when he begrudgingly helps you with a problem. Coincidence seats you next to him on the flight, where he discovers you’re quietly funny despite your shyness. You part ways at baggage claim—only to reunite the next day at Nelson Road, where Roy learns you’re a new part-owner of Richmond.

——————————

1. The airport encounter

Airports had never been your favorite place. Too many people, too much noise, too much unpredictability. And yet, here you were—stuck in the middle of a crowded terminal, anxiety coiling tightly in your chest as the self-check-in kiosk refused to cooperate.

You frowned at the screen, double-checking your details. Everything was correct. Your name, your flight number, your passport. And yet, the machine blinked back at you with an unhelpful error message.

Your stomach twisted.

A line was forming behind you. You could hear the subtle shuffling of shoes, the impatient clearing of throats. You hated holding people up, being a problem. Your fingers hovered over the screen, unsure whether to try again or just step aside and hope someone at the desk could help.

Before you could decide, a deep, gravelly voice cut through the noise.

“Oh, for fuck’s sake.”

The sheer exasperation in it made you freeze. You turned slightly, heart already sinking as you prepared to face whoever was behind you.

And that’s when you saw him.

Roy Kent.

Dressed in dark joggers and a fitted t-shirt, arms crossed, scowling like this whole airport was his mortal enemy. His dark eyes flicked from the screen to you, then back again, his jaw working as he exhaled sharply.

You knew who he was. Of course you did. Even if you weren’t a football fan, you’d have to be living under a rock not to recognize Roy Kent. But knowing him and being directly in his line of sight while currently being incredibly in the way were two very different things.

“I—” Your voice came out too quiet, barely audible over the sounds of the terminal. You swallowed, fingers tightening around your passport. “It’s fine, I can—”

Roy made a noise that was somewhere between a grunt and a sigh before stepping forward. “Move.”

You stepped aside instinctively, heat creeping up your neck as he took your place in front of the kiosk. With quick, efficient movements, he started tapping through the options, muttering under his breath.

“Fucking machines. More complicated than they need to be. No wonder people lose their shit in airports.”

You stood frozen beside him, barely processing what was happening. Roy Kent—gruff, intimidating, ex-professional footballer Roy Kent—was helping you.

In the most reluctant, aggressively impatient way possible, but still. Helping.

A few more jabs at the screen, and suddenly, the kiosk beeped, printing your boarding pass like it had never been an issue in the first place.

Roy tore the ticket off and shoved it toward you, not unkindly. “Sorted.”

You blinked, hesitating before taking it. “I—thank you.”

Roy grunted, already grabbing his own passport. “Yeah, whatever.”

You hovered for a moment, unsure whether to say something else or just scurry away before you embarrassed yourself further. Before you could decide, the machine stalled on him, flashing the same error message it had given you.

You pressed your lips together, fighting the involuntary urge to laugh.

Roy turned his head slowly, fixing you with a flat stare. “You laughing?”

You swallowed it down immediately. “No.”

His eyes narrowed slightly, but there was no real anger there—just mild suspicion. Then he turned back to the machine and exhaled sharply.

“Fucking karma.”

This time, you did laugh—quiet, barely there, but real. And for a split second, Roy Kent’s scowl softened.

—

You didn’t expect to cross paths with him again after that.

The airport was huge, with countless gates and terminals, and yet, somehow, you found yourself trailing behind him through security. Not on purpose—just pure, unfortunate coincidence.

If he noticed, he didn’t comment.

Security had never been an issue for you before, but your nerves spiked when the officer asked you to step aside for a random screening. You knew it was routine, but standing there, separated, feeling like you were being watched, made your breath come a little shorter.

You shifted uncomfortably as they patted you down, checking your bag with a little more scrutiny than necessary. You tried not to let it get to you, but the extra attention made you feel small, like you’d somehow done something wrong.

You were too caught up in your own head to notice Roy standing just a few feet away, waiting.

It wasn’t until you were finally cleared that you saw him, arms crossed, face as unreadable as ever.

You blinked, thrown.

He didn’t look at you directly, just let out a gruff, “Took your fucking time,” before turning toward the main terminal.

You hesitated, unsure what to make of it. He didn’t need to wait for you. It wasn’t like you were traveling together.

But maybe… maybe he just didn’t like leaving someone behind.

That thought settled in your chest as you fell into step a few paces behind him, moving toward the gates.

And somehow, you felt a little less lost.

————————

2. The Flight

Airports were one thing—overcrowded, chaotic, and stressful. But planes? Planes were worse.

You weren’t exactly afraid of flying, but the entire process—boarding, finding your seat, being trapped in a metal tube with a hundred strangers—always made you uneasy. You preferred blending into the background, avoiding attention. But that was hard to do when you stepped onto the plane, checked your ticket, and saw him.

Roy Kent.

Sitting in the window seat of your row.

Of course.

You hesitated in the aisle, double-checking your ticket as if you’d somehow misread the number. But no. There it was, clear as day: Seat 13B. Right next to Roy Kent.

He looked up at the same time, his expression flat and unreadable. “Fucking hell,” he muttered.

You startled slightly. “What?”

Roy exhaled, dragging a hand down his face. “Nothing.” He shook his head, shifting slightly so you could squeeze into your seat.

You moved quickly, stuffing your bag under the seat and fastening your seatbelt. The plane was still boarding, people shuffling around you, but you kept your head down, focusing on your hands in your lap.

Beside you, Roy sat with his arms crossed, his leg bouncing slightly. He seemed tense. More than usual.

You swallowed, debating whether to say something. He had helped you—gruffly, reluctantly, but still. And you weren’t exactly the best at making conversation, but maybe…

“You don’t like flying?”

Roy turned his head slightly, one brow raised. “What?”

You cleared your throat, keeping your voice soft. “You just seem tense.”

He huffed. “Course I’m tense. We’re about to be in the fucking air.”

A small smile tugged at the corner of your lips. “You know that’s how planes work, right?”

Roy shot you a look, but there was no real heat behind it. “Yeah, I fucking know. Doesn’t mean I have to like it.”

That made you bite back a laugh. It was such a normal complaint, but coming from Roy Kent—the ex-footballer, the hard-edged coach who seemed like nothing could rattle him—it was oddly endearing.

You hesitated, then quietly admitted, “I don’t really like it either.”

Roy glanced at you, his leg still bouncing. “Yeah?”

You nodded, playing with the hem of your sleeve. “I don’t like feeling trapped. And takeoff always makes my stomach drop.”

Roy grunted. “Yeah, that part’s fucking awful.”

A beat of silence passed. Then, to your surprise, he said, “Keeley used to make me hold her hand during takeoff.”

Your stomach twisted slightly at the mention of her—his ex—but he didn’t sound sad. Just stating a fact.

You hesitated. Then, voice barely above a whisper, you said, “Do you want me to?”

Roy turned to look at you fully. You immediately regretted it, face heating up under his gaze.

“Forget it,” you muttered quickly, shaking your head. “That was stupid, I—”

But before you could finish, Roy reached over and, without a word, took your hand.

Your breath caught.

His grip was warm, solid—not too tight, just enough to ground you. His thumb brushed over the side of your palm, a small, absent motion.

You stared at your joined hands, completely thrown. “Oh.”

Roy scoffed, but there was a flicker of amusement in his eyes. “Don’t make it fucking weird.”

You ducked your head, hiding a small, nervous smile. “I won’t.”

The plane began to taxi, the flight attendants giving their final safety instructions. You focused on your breathing, your pulse steadying slightly as Roy’s hand remained in yours.

And when the plane finally took off, your stomach still dropped—but somehow, it wasn’t as bad as usual.

—————————

3. In the Air

The plane had been in the air for about thirty minutes, and to your mild surprise, Roy hadn’t let go of your hand until the seatbelt sign turned off. He released it with a gruff little noise, muttering something under his breath about turbulence being bollocks. You didn’t push it, simply flexing your fingers, pretending not to notice the warmth that lingered there.

Now, you were both settled in, and the flight attendants were moving through the cabin, offering drinks and snacks. You kept yourself tucked into your seat, watching as Roy pulled out a book from his bag—a well-worn paperback with a cracked spine.

You blinked. “You read romance novels?”

Roy didn’t even glance at you. “Yeah. What of it?”

You pressed your lips together, trying very hard not to smile. “Nothing. I just wouldn’t have guessed.”

“Yeah, well,” he grunted, flipping a page, “they’re good. And they don’t fuck about.”

You tucked that bit of knowledge away for later, watching as the flight attendant reached your row. Roy ordered a whiskey. You asked for a tea, adding a polite thank you as the woman handed it over.

As the attendant moved on, Roy huffed a quiet laugh.

You frowned slightly. “What?”

“Nothing,” he said, shaking his head. “Just funny. You say thank you like you think it might piss someone off.”

Your face warmed. “I just don’t like bothering people.”

Roy gave you a look, unimpressed. “It’s their job.”

“I know that,” you mumbled. “But still.”

There was a pause. Then, to your surprise, Roy smirked slightly. “Bet you apologize when someone bumps into you, don’t you?”

You took a sip of your tea, avoiding his gaze. “…No.”

Roy let out a short, rough chuckle. “Fuckin’ knew it.”

You bit your lip, trying to suppress a smile.

For the next half-hour, Roy read while you stared out the window, watching the clouds roll by. The soft hum of the plane filled the space between you, not uncomfortable, but steady—companionable, even.

At one point, Roy shut his book with a sigh, rubbing his eyes.

“Something wrong?” you asked softly.

“Nah.” He stretched, rolling his shoulders. “Just read this one before. Forgot how it ended.”

You tilted your head. “Isn’t that a good thing? If it’s worth reading again?”

Roy blinked, as if he’d never considered that. Then he grumbled, “Guess so.”

You smirked. “So, what’s it about?”

Roy eyed you, as if debating whether to actually tell you. But then he leaned back and said, “Two idiots. Fall in love. Fuck about for half the book before they actually get their shit together.”

You exhaled a small laugh. “So, every romance novel ever?”

Roy made a noise of agreement. “Yeah. But this one’s got a dog.”

You bit your lip, trying very hard not to giggle. “And that makes it better?”

“Fucking obviously.”

You snorted, covering your mouth. Roy turned to glance at you, brow raised.

“Did you just snort?”

You groaned, sinking lower into your seat. “Forget it.”

Roy smirked, looking deeply pleased with himself. “Didn’t think you had that in you.”

You crossed your arms, fixing your gaze on the seat in front of you. “I can be funny.”

Roy made a skeptical noise. “You’re too quiet.”

Your lips twitched. “You just have to listen harder.”

Roy huffed, but there was something warm in his expression—something amused and maybe a little curious. Like he was starting to pay attention in a way he hadn’t before.

The flight continued on, and somehow, you weren’t dreading the hours ahead quite as much.

—————————

4. The Landing

The captain’s voice crackled over the intercom, announcing that they’d be descending into London soon. You sat up a little straighter, stretching out your stiff limbs, but as soon as the plane started its slow tilt downward, a familiar unease crept in.

You weren’t exactly afraid of flying—but turbulence? That was another thing entirely.

The first few bumps weren’t too bad, just mild shudders through the cabin. You could handle that. You could breathe through that. But then the plane jolted harder, and your fingers curled around the armrests, stomach twisting as if the ground was dropping out from beneath you.

Roy must have noticed, because he muttered, “You alright?”

You gave a tight nod, not trusting your voice.

The plane shuddered again, dipping slightly, and you sucked in a sharp breath, grip tightening.

Roy exhaled through his nose. “Fuck’s sake.” Then, before you could process it, you felt his hand close over yours, pulling it away from the armrest.

You blinked, startled, looking down at your joined hands. His was warm and solid, rougher than yours, calloused from years of football. He wasn’t squeezing, just holding, steady and grounding.

Your face burned. “Roy—”

“S’just turbulence,” he muttered. “Plane’s not gonna fall out of the fuckin’ sky.”

You swallowed hard. “I know that.”

“Do you?” His thumb brushed over the back of your hand absently, like he wasn’t even thinking about it. “Because you look like you’re about to shit yourself.”

Despite the tension coiled in your chest, a startled laugh escaped you. “I hate you.”

“No, you don’t,” Roy said, squeezing your hand briefly before letting go.

You hesitated, fingers twitching where they rested on your lap, before exhaling and forcing yourself to relax. “I just—don’t like not being in control, I guess.”

Roy hummed. “Yeah. Shit feeling, that.”

You glanced at him, surprised at his easy agreement. There was something understanding in his tone, something that made you wonder if he was thinking about football, about injuries, about everything that had changed in his life over the past few years.

The plane jolted one last time, but this time, you managed to breathe through it. When the wheels finally hit the runway, a rush of relief filled your chest.

Roy sighed like he was personally offended by the rough landing. “Jesus Christ.”

You let out a small breathy laugh. “I thought you weren’t scared of flying.”

“I’m not,” he grumbled. “But that was fucking shit.”

As the plane slowed, passengers started unbuckling and standing up, reaching for their luggage. You sat for a moment, letting the reality sink in—you were back in England, back to work, back to your life. The stress that had been sitting in the back of your mind started creeping forward again.

Roy stretched, rolling his shoulders. “Got bags to pick up?”

You blinked. “Oh—yeah. Just one.”

Roy nodded. “C’mon, then.”

And just like that, without thinking, he waited for you to step into the aisle first, following as if it was the most natural thing in the world.

—————————-

5. The Unexpected Reunion

Roy had assumed that was the last he’d see of you.

After all, airports were just liminal spaces—places where people drifted in and out of each other’s lives, where fleeting moments happened between layovers and long flights but never really lasted. You’d had your strange little moment together on the plane, but once you’d both grabbed your bags at baggage claim, you’d given him a small, polite smile—Thanks for the company—and then disappeared into the crowd.

And that was that.

Or so he’d thought.

The next morning, Roy trudged into Nelson Road, half-dreading the strategy meeting he had to sit through. Meetings weren’t his thing—too much talking, not enough doing. He was already bracing for Higgins’ rambling when he pushed open the door to Rebecca’s office—

—And stopped in his fucking tracks.

There you were.

Sitting in one of the chairs across from Rebecca’s desk, back straight, hands neatly folded in your lap. The same woman he’d sat next to for nearly twelve hours yesterday. The one who’d muttered quiet little jokes under her breath, making him laugh when he hadn’t meant to. The one whose hand he’d held without thinking when she’d gone rigid with turbulence.

You looked different here. More polished. More serious. Your hair was styled, your posture poised, and there was a quiet confidence in the way you listened to Rebecca and Higgins. But as your eyes flickered to his, he caught the same flicker of Oh, shit in your expression that he was feeling himself.

He stopped short, frowning. “What the fuck?”

Rebecca, utterly unfazed, glanced up. “Good morning, Roy.”

He didn’t look away from you. “What—why is she—” He gestured vaguely, still processing.

You cleared your throat, shifting slightly. “Hi, Roy.”

Rebecca arched a brow. “You two know each other?”

You hesitated. “We—met at the airport.”

Roy crossed his arms. “She sat next to me on the plane.”

Higgins beamed. “Oh, what a lovely coincidence!”

Roy ignored him, still staring at you like he was trying to figure out what the fuck was going on.

Rebecca leaned forward, hands clasped on her desk. “As I was saying before you barged in, Roy—she’s going to be involved with the club moving forward.”

His frown deepened. “How?”

You exhaled, clearly prepared for this question. “My family has a long history with Richmond. My grandfather was an investor years ago. When he passed, my father took over, but he didn’t have much interest in football. I…do. So I’ve bought in as a partial owner.”

Roy just stared at you.

Because, yeah, that made perfect fucking sense, didn’t it? That he’d randomly meet you, some quiet, anxious-but-secretly-funny woman on a flight, think nothing of it, and then the next day, bam, you were partially in charge of the club he worked for.

Absolutely fucking ridiculous.

Rebecca, meanwhile, was smiling, clearly enjoying his shock. “She’ll be sitting in on meetings, observing the team, getting a feel for things.”

Roy dragged a hand down his face. “Jesus Christ.”

That was not what he’d expected walking into this room today.

And then, because things clearly weren’t ridiculous enough, the door burst open, and in came Ted, Beard, and some of the players—Jamie, Isaac, and Colin, already mid-conversation.

Ted’s face brightened immediately when he saw you. “Well, hey there! You must be the new addition Rebecca was talkin’ about.”

You smiled, albeit a little shyly. “Hi. It’s nice to meet you.”

Ted, as he always did, took that as an invitation to shake your hand enthusiastically. “Welcome aboard! We’re all about teamwork and good vibes here. Oh, and biscuits. Have you tried Rebecca’s biscuits yet?”

Rebecca rolled her eyes. “We are in the middle of a meeting.”

Meanwhile, Jamie, who had been watching this exchange with keen interest, suddenly grinned and nudged Roy with his elbow. “Wait—this the bird you were talking to in the airport?”

Roy glared at him. “Shut the fuck up.”

Colin let out a low whistle. “Damn, Coach. You work fast.”

You looked between them, confused, while Roy debated murder. “I—what?”

Before you could ask, Beard, ever the observer, tilted his head. “Interesting,” he mused, glancing between the two of you. “So the grump met the introvert. What a fascinating dynamic.”

Roy was already fucking done with this conversation.

He grumbled something under his breath and dropped into an empty seat, arms crossed, brow furrowed.

But his gaze, against his better judgment, kept flickering to you.

And to his irritation, he found himself thinking—

Well. This could get interesting.

—————————

6. A Tour, Not a Date (Definitely a Date)

For the rest of the meeting, Roy stayed quiet, arms crossed, looking like he was half-listening, half-replaying the last 24 hours in his head. Every now and then, his eyes flicked to you—watching as you nodded along to Rebecca’s words, or asked a quiet, thoughtful question that made Higgins ramble enthusiastically.

And if he was really fucking paying attention (which he wasn’t, obviously), he might’ve noticed that whenever he glanced at you, you were already looking at him.

After the meeting, as everyone filed out, Roy hung back, watching as you lingered near Rebecca’s desk, flipping through some notes. The others had mostly cleared the room, except for Higgins, who was attempting to organize a stack of papers he’d already dropped twice.

You seemed…hesitant. Not lost, exactly, but like you weren’t sure what to do next.

Roy sighed. Fucking hell.

He wasn’t about to feel bad for someone. That wasn’t his thing. But still, he found himself stepping toward you anyway, clearing his throat.

“If you’re gonna be sticking around, you should probably see the place properly.”

You blinked up at him. “Oh. I—yeah, that’d be nice.”

He grunted, jerking his head toward the door. “C’mon, then.”

You followed him out, walking alongside him as he led you down the halls of Nelson Road. He wasn’t exactly graceful about it—Roy Kent was no tour guide—but he pointed out different rooms in his usual blunt fashion.

“That’s the gym. Physio’s office is next door. Boot room’s down there—smells like fuckin’ death, don’t go in unless you have to.”

You made a quiet noise—somewhere between a laugh and a hum—as you kept pace with him.

He continued, showing you the players’ lounge, the kitchen, and finally, the pitch. When you stepped onto the empty field, you took a slow breath, glancing up at the stadium around you.

“This must feel… different when it’s full.”

Roy shoved his hands in his pockets. “Yeah. Louder. Feels alive, then.”

You nodded, thoughtful. “I’d like to see that.”

He eyed you for a moment, then, before he really knew what he was doing, he muttered, “You will.”

You turned toward him, curiosity flickering in your expression. But you didn’t press.

Roy, feeling weirdly self-conscious, exhaled sharply. “You eaten?”

You tilted your head. “Not since the plane.”

“Right.” He scratched at his beard, looking away. “There’s a pub not far from here. Good food.”

Your lips parted slightly, like you were surprised by the offer. “Are you… inviting me to dinner?”

He scoffed. “It’s food.”

“So, not a date?”

“Course not.” He avoided your gaze. “Just food.”

You bit your lip, amusement glinting in your eyes. “Okay. Just food.”

He grunted, leading you toward the exit.

What neither of you noticed was the way a few of the players—Isaac, Colin, and Jamie—had been lingering in the hallway, having caught the entire exchange.

Colin smirked. “Did Coach Kent just ask someone to dinner?”

Jamie let out a dramatic gasp. “Fuckin’ hell, it’s a Christmas miracle.”

Isaac just grinned. “You see how he listens to her? Like, actually listens?”

They all turned to Beard, who had been watching too, stroking his beard in thought.

“Fascinating,” he murmured.

—

Dinner (or not dinner, as Roy insisted) turned out to be surprisingly easy. You weren’t one for big conversations, but you had a sharp sense of humor, and Roy found himself genuinely enjoying the quiet back-and-forth.

At one point, you leaned forward slightly, resting your chin on your hand. “You know,” you mused, voice still soft but carrying a distinct edge of amusement, “for someone who likes to act like he doesn’t care about anything, you’re really bad at hiding it.”

Roy paused, fork halfway to his mouth. He stared at you.

And then, to your clear surprise—

He smirked.

“Yeah?” he muttered. “And you? You pretend to be shy, but you’re a cheeky little shit, aren’t you?”

Your eyes widened, lips parting in silent protest. But then—then—you grinned.

Roy Kent was fucked.

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