The Holiday Arrangement: How A Fake Relationship With A Best Friend Turned Into Something Real

Madison’s mother looked like she might faint from joy. Her grandmother was openly cackling with delight, and her sister looked somewhere between impressed and annoyed that Madison had apparently won the boyfriend competition.

«Well,» her mother said, composing herself, «this is certainly—wonderful. Unexpected, but wonderful. We’re so happy for you, sweetheart.»

She pulled Madison into a tight hug and whispered in her ear, «He looks at you like you hung the moon. Don’t let this one go.»

Madison’s throat tightened. If only her mother knew the truth: that it was all an act, a performance, a carefully constructed lie. Even if, for a moment there in his arms, it had felt devastatingly real.

This was a terrible idea. Christopher had closed billion-dollar deals without breaking a sweat. He’d given presentations to hostile board members. He’d negotiated with some of the most ruthless business people in the world. But nothing—absolutely nothing—had prepared him for the feeling of waking up with Madison Carter in his arms.

He stood in the shower, letting cold water pour over him, trying to regain some semblance of control. His body had betrayed him spectacularly that morning, and worse, his mouth had too. «You smell incredible.» What the hell had he been thinking?

He hadn’t been thinking; that was the problem. He’d been half asleep, wrapped around the woman he’d been secretly in love with for three years, and his stupid, sleep-addled brain had just said it out loud.

The worst part? It was true. She did smell incredible, like vanilla and something floral he could never quite identify, but that made him want to bury his face in her hair and never leave.

Christopher turned off the water and stared at himself in the mirror.

«Get it together, Rivera. You’re pretending. That’s all this is. Pretending.»

Except it didn’t feel like pretending when he’d held her. It had felt like coming home.

«So, Christopher,» Madison’s grandmother said, settling into the couch like she was preparing for a long interrogation session, «tell me, what are your intentions toward my granddaughter?»

They’d moved to the living room after breakfast, and Madison was perched on the armchair while Christopher sat on the couch, looking far too comfortable for someone who should be terrified.

«My intentions are completely honourable, Mrs. Peterson,» he said with that charming smile that probably closed deals and broke hearts in equal measure.

«That’s boring. I want details. When are you proposing? How many children do you want? Are you good with your hands?»

«Grandma,» Madison buried her face in her hands.

«What? I’m eighty-two. I’ve earned the right to be inappropriate.»

Christopher laughed, that real laugh that Madison loved. «I appreciate your directness. To answer your questions: when the time is right; I’m thinking two or three; and I’ve been told I’m quite skilled with my hands.»

Madison choked on her coffee. Her sister, Layla, leaned forward.

«Okay, but I have to know, how did you actually get together? Like, what made you finally tell her you had feelings?»

Christopher glanced at Madison, and she saw something flicker in his eyes.

«It was her birthday. She’d had a terrible day. Deadline stress. An argument with her editor. I showed up at her apartment with her favourite Thai food and those terrible romantic comedies she pretends not to love.»

That had actually happened. Six months ago. Madison remembered it vividly.

«We were on her couch,» he continued, his voice softer now. «And she laughed at something in the movie, and I just looked at her. Really looked at her. And I realised I was tired of pretending I didn’t want this—didn’t want her—every single day.»

The room had gone quiet. Even Madison’s grandmother wasn’t making jokes.

«So I told her,» Christopher said, his blue eyes locked on Madison’s. «I said, ‘I’m in love with you. I have been for a while. And I know this might ruin everything, but I can’t keep pretending I’m not.'»

Madison’s heart was hammering. That hadn’t happened. None of that had happened. So why did it sound so real? Why did she wish it had?

«And what did you say?» her mother asked Madison gently.

Madison swallowed hard. «I told him I’d been waiting for him to figure it out for two years.»

Christopher’s expression shifted. Surprise? Confusion? Something she couldn’t quite name. Because that part was true. She had been waiting. She just hadn’t admitted it to herself until right now.

Later that afternoon, Madison’s cousin Andrew arrived. He was twenty-nine, worked as a data analyst, and had an unfortunate habit of treating real life like one of his case files.

«So Christopher Rivera,» Andrew said, shaking Christopher’s hand with a grip that was slightly too firm. «Madison’s told us absolutely nothing about you, which I find fascinating. Usually, she overshares about everything.»

«Andrew, be nice,» Madison warned.

«I am being nice. I’m just curious.» He pulled out his phone. «Quick compatibility test. Madison, what side of the bed does Christopher sleep on?»

«Left,» Madison answered immediately.

«Christopher, what’s Madison’s coffee order?»

«Two sugars, extra cream, shot of vanilla,» Christopher said without hesitation.

Andrew frowned, clearly hoping to catch them in a lie. «Madison, what’s Christopher’s middle name?»

Madison opened her mouth, then closed it. She actually didn’t know his middle name.

«Alexander,» Christopher supplied. «She knows it. She just likes to make me sweat.»

Andrew wasn’t convinced. «Christopher, what’s Madison’s biggest fear?»

«Being forgotten,» Christopher said quietly. «Not death. Not failure. She’s afraid that she’ll leave this world without having made any real impact. That her stories won’t matter. That she won’t matter.»

The room went silent. Madison stared at him, her throat tight. He was right. He was absolutely right. She’d never told him that directly, but somehow he knew.

«Also spiders,» Christopher added with a small smile. «She’s terrified of spiders.»

The tension broke. Everyone laughed, including Madison, though her eyes were suspiciously bright. Andrew looked grudgingly impressed.

«Okay, you pass—for now. There will be more tests.»

Christopher looked amused. «Oh, absolutely. I have a whole list. This is just the warm-up round.»

And that evening, after her family finally left («We’ll be back tomorrow for lunch,» her mother had promised/threatened), Madison collapsed onto the couch.

«Your family is exhausting,» Christopher said, sitting next to her.

«I warned you.»

«You really did.» He turned to look at her, his expression unreadable. «What you said earlier—about waiting for me to figure it out…»

Madison’s heart skipped. «I was improvising—playing the part.»

«Were you?»

The question hung between them, heavy with implications.

«Chris—»

«Because I wasn’t—» He shifted closer, and Madison’s breath caught. «When I said I couldn’t stop thinking about you—that I was tired of pretending—I wasn’t acting, Madison.»

«Don’t,» she whispered. «Don’t say things like that if you don’t mean them.»

«What if I do mean them?»

He reached up, tucking a strand of hair behind her ear. His fingers lingered on her cheek, and Madison felt like she was burning from the inside out.

«We’re supposed to be pretending,» she said, but her voice was shaky.

«I know.» His thumb traced her jawline, and she shivered. «But right now there’s no one watching—no one to fool. It’s just us.»

«That’s what scares me.»

Christopher smiled, sad and understanding. «Me too.»

They sat there in the quiet apartment, the space between them charged with everything unsaid. Madison wanted to lean in, wanted to close the distance, wanted to know what his lips would feel like against hers. But if they crossed that line, there would be no going back, and she wasn’t sure she was brave enough to risk losing her best friend for something that might just be temporary insanity brought on by proximity and fake dating.

«We should probably rebuild the pillow wall,» she said finally.

«Probably a good idea.»

Neither of them moved.

«Madison?»

«Yeah?»

«For what it’s worth, I don’t regret waking up with you in my arms this morning. I just regret that it surprised you—that it made you uncomfortable.»

«It didn’t make me uncomfortable,» she admitted quietly. «That’s what scared me.»

His blue eyes darkened. «Then we’re both in trouble—serious trouble.»

Christopher stood, extending his hand to help her up. When she took it, he pulled her close, not into an embrace, just close enough that she could feel his warmth, could see the conflict in his eyes that probably mirrored her own.

«Tomorrow’s going to be harder,» he said. «More family, more questions, more pretending. Can you handle it?»

He smiled, but it didn’t quite reach his eyes. «The pretending isn’t the hard part anymore, Madison. The hard part is remembering that this has an expiration date.»

He disappeared into the bedroom, leaving Madison standing in the living room, her hand still warm from his touch, her heart tangled in knots she had no idea how to unravel. This was only day two. They had twelve more days of this. Madison had a terrible feeling that by the end of two weeks, her heart wasn’t going to be the only thing she’d lost to this charade.

Madison woke up the next morning to find herself once again wrapped around Christopher like a koala on a tree. This was becoming a very dangerous pattern. His arm was around her waist, her head tucked under his chin, their legs impossibly tangled. The pillow wall they’d carefully reconstructed last night had apparently declared defeat and vanished somewhere during the night.

But this time Christopher was already awake. She could tell by his breathing—too controlled, too deliberate. He was lying perfectly still, probably terrified of waking her up, possibly having an internal crisis about their current position.

Madison kept her eyes closed, torn between pretending to still be asleep and acknowledging the elephant—or rather, the full-body contact situation—in the room.

«I know you’re awake,» Christopher said quietly, his voice rumbling through his chest and into her ear.

«How?»

«Your breathing changed.»

«That’s creepy.»

«That’s observant.»

She felt him smile against her hair.

«We should probably talk about this. About how your bed has a magnetic force that pulls us together? About how neither of us seems to mind it very much?»

Madison’s heart stuttered. She pulled back just enough to look up at him, and immediately regretted it. His hair was messy from sleep, his blue eyes were soft in the morning light, and he was looking at her with an expression that made her chest ache.

«Chris…»

Her phone exploded with sound. Both of them jumped as Madison’s alarm shrieked, followed immediately by three text messages that pinged in rapid succession. Madison grabbed her phone, grateful for the interruption even as she mourned it.

Mom: Lunch at noon. Don’t be late. Derek is coming.

Grandma: Wear something pretty. First impressions matter, even though you already made a very good impression yesterday with that shirtless situation.

Layla: Can’t wait for you to meet Derek. He’s so excited to meet your Christopher.

«Derek’s coming,» Madison said, showing Christopher the messages.

«Your sister’s fiancé? The perfect one?»

«Doctor. Volunteers at free clinics. Probably rescues puppies in his spare time.»

Christopher sat up, running a hand through his already messy hair. «Sounds intimidating.»

«You’re a tech CEO who was on the cover of Forbes. I think you can handle a doctor.»

«It’s not a competition.»

«Everything is a competition in my family. You’ll learn.»

Three hours later, Madison stood in front of the bathroom mirror, trying on her fifth outfit. Nothing looked right. Everything was either too casual or trying too hard.

«You look beautiful,» Christopher said from the doorway.

She jumped. «How long have you been standing there?»

«Long enough to watch you reject four perfectly good outfits.» He walked in, and the bathroom suddenly felt very small. «What’s wrong with this one?»

«It’s too… I don’t know, plain? You’re nervous.»

«I’m not nervous.»

«Madison.» He turned her to face him, hands on her shoulders. «You’re my fake girlfriend, remember? I’m supposed to think you’re the most beautiful woman in the world. Which, for the record, isn’t hard to pretend.»

Her breath caught. «Christopher…»

«Let me finish.» His hands slid down her arms, leaving goosebumps in their wake. «You’re going to walk into that lunch, and your sister’s perfect fiancé is going to be there, and you’re going to feel like you’re being compared. But here’s the thing. I’m not comparing you to anyone. To me, there is no comparison.»

«You’re really good at this fake boyfriend thing,» she whispered.

«What if I’m not pretending?»

Before she could respond, her phone rang. Her mother. Of course.

«We’re on our way,» Madison said, answering it. «Yes, we’re both dressed. No, I don’t need you to—Mom, we’re adults. Okay, fine. Yes, we’re leaving now.»

She hung up and looked at Christopher. «We should go.»

«We should talk about what I just said.»

«We should definitely not do that right now.» She grabbed her purse, her heart racing. «Come on. Time to meet Dr. Perfect.»

The restaurant her mother had chosen was, of course, the fanciest one in town. White tablecloths, crystal glasses—the kind of place where the menu didn’t have prices because if you had to ask, you couldn’t afford it. Madison’s family was already there, seated at a large table, and next to Layla sat a man who looked like he’d stepped out of a medical drama: handsome, clean-cut, wearing a smile that was probably meant to be charming but came across as slightly plastic.

«Madison! Christopher!» Her mother waved them over enthusiastically. «Come meet Derek.»

Derek stood, extending his hand to Christopher first. «You must be the famous Christopher Rivera. I’ve read about your company. Very impressive.»

«Thanks,» Christopher said, shaking his hand. «And you’re the surgeon, right?»

«Cardiothoracic. I specialize in paediatric cases.» Derek turned to Madison, his smile widening. «And you must be the talented writer. Layla talks about you all the time.»

«Does she?» Madison glanced at her sister, who was beaming.

They settled into their seats, Christopher’s hand immediately finding Madison’s under the table, his thumb tracing soothing circles on her palm.

«So, Christopher,» Derek said, leaning forward, «how did a tech CEO end up with a romance novelist? Seems like an unusual pairing.»

«Opposites attract,» Christopher said smoothly. «Though we’re not as opposite as you’d think. We both solve problems for a living. I just do it with code, and Madison does it with words.»

«How poetic,» Derek said, and Madison couldn’t tell if he was being sincere or condescending.

Andrew, the cousin detective, seized his opportunity. «Speaking of poetry, Christopher, what’s Madison’s favorite book?»

«Pride and Prejudice,» Christopher answered without hesitation. «But she has a secret soft spot for The Princess Bride.»

Madison squeezed his hand under the table. He was right on both counts.

«And Madison,» Andrew continued, «what’s Christopher’s biggest pet peeve?»

«People who don’t listen,» Madison said. «He hates when people interrupt or when they’re looking at their phones while someone’s talking to them. He values genuine connection.»

Christopher’s hand tightened on hers. Derek watched this exchange with interest.

«You two seem very in sync.»

«They do, don’t they?» Layla said, smiling at her sister. «It’s actually kind of adorable.»

Throughout lunch, Madison noticed Derek was everything he appeared to be: polite, accomplished, well-mannered. He asked appropriate questions, laughed at appropriate times, and treated Layla with appropriate affection. He was perfect and absolutely, completely boring.

Madison looked at Christopher, who was currently telling her grandmother some ridiculous story about a failed business pitch that involved a broken projector and a very confused janitor. Her grandmother was cackling with laughter, and even her mother was smiling. Christopher caught her looking and winked. Her stomach flipped.