The Bet He Wasn’t Supposed to Win
McKenzie Shinabery · Completed · 131.3k Words
Introduction
Bad boy. Trouble. Walking red flag.
So when he asks Ellie Marrow out—quiet, rule-following, and painfully invisible—it’s obvious to everyone that it has to be a joke.
Except Ellie knows the truth.
Jaxon made a bet. A stupid, reckless one. And she’s the prize.
Instead of saying no, Ellie makes a choice no one expects: she agrees to fake date him—for her own reasons. With rules. Boundaries. And an expiration date. What starts as pretending quickly turns complicated as Ellie sees the side of Jaxon no one else does.
As rumors spread and lines blur, Ellie must decide who she wants to be when she stops playing it safe. And Jaxon has to face the truth about himself—and the damage a single lie can cause.
Because when pretending feels this real, someone is bound to get hurt.
Chapter 1
Jaxon Reed hadn’t planned on coming to the bonfire.
He especially hadn’t planned on standing at the edge of it, hands shoved into his jacket pockets, replaying the exact moment Brielle Vaughn told him they were done.
I just think we want different things, she’d said, flipping her glossy hair over her shoulder like she wasn’t gutting him in the middle of the hallway. Like it didn’t matter that half the cheer squad had been within earshot. Like he hadn’t been useful to her just long enough to stop being interesting.
Now the night air felt colder than it should’ve, smoke curling into the dark sky while Crestwood High did what it always did after a home game—laughed, flirted, pretended nothing ever went wrong.
“Dude,” Dylan said, nudging him with an elbow. “You look like someone kicked your dog.”
“I don’t have a dog,” Jaxon muttered.
“Exactly,” Mason added from the tailgate of Evan’s car. “That’s how bad it is.”
Jaxon shot him a look but didn’t argue. He didn’t feel like himself tonight. He felt hollow. Tired in a way sleep didn’t fix.
Evan passed him a soda. “You didn’t even stay till the end of the game.”
“Had stuff,” Jaxon said.
Xavier had been sick again. His mom had texted twice during third quarter. Jaxon hadn’t answered either message, guilt sitting heavy in his chest.
“Stuff,” Mason repeated. “You mean Brielle.”
Jaxon stiffened. “Drop it.”
“Oh, come on,” Dylan said. “Everyone saw it coming.”
“Did they?” Jaxon snapped, sharper than he meant to.
Silence fell for a beat. Evan raised his hands. “Hey. We’re just trying to cheer you up.”
Mason hopped down from the truck and stepped closer, eyes bright with that familiar mix of boredom and trouble. “Which is why,” he said slowly, “we’re not letting you mope all night.”
“I’m not moping.”
“You absolutely are.”
Jaxon exhaled, gaze drifting back to the fire. Brielle stood on the other side now, laughing with her friends like she hadn’t shattered his pride six hours ago. She hadn’t even looked his way once.
“Forget her,” Dylan said. “You’re Jaxon Reed. She doesn’t get to decide your worth.”
“Yeah,” Mason added. “You could get anyone here if you wanted.”
Jaxon scoffed. “That’s not the point.”
“Isn’t it?” Mason asked. “Because she made you look like you lost.”
The words hit where Jaxon hadn’t braced himself.
Mason turned, scanning the crowd. His gaze lingered, then stopped. “Alright. Prove it.”
Jaxon frowned. “Prove what?”
“That you didn’t lose.”
Jaxon followed Mason’s stare.
Ellie Marrow stood near the parking lot, slightly apart from the bonfire glow. She wore a soft cardigan and hugged a planner to her chest, listening as Sophie Alvarez talked animatedly beside her. Ellie smiled, small, genuine, like she wasn’t performing for anyone.
She looked… untouched by all of this.
“That’s messed up,” Evan said quietly.
“Relax,” Mason replied. “I’m not saying mess with her. Just ask her out.”
Jaxon shook his head. “No.”
“Why?” Dylan asked. “She’s cute. Smart. And she’s not Brielle.”
The last part landed heavier than the rest.
“She’s safe,” Mason said. “No drama. No competition. She says yes, everyone knows Brielle didn’t matter.”
Safe.
The word sat wrong in Jaxon’s chest.
He watched Ellie tuck hair behind her ear, her smile small but genuine. She wasn’t performing. She wasn’t trying to be seen.
And suddenly, the idea of dragging her into his mess made his skin itch.
“That’s not happening,” Jaxon said.
Mason sighed dramatically. “You’re no fun anymore.”
Evan nodded. “Let it go.”
But Brielle’s laugh cut across the fire again—sharp, careless—and something inside Jaxon snapped. Not anger. Pride.
“Fine,” he said.
The word slipped out before he could stop it.
Mason froze. “Yeah?”
Jaxon exhaled slowly. “Two weeks,” he added quickly. “If I ask her out.”
Dylan grinned. “There it is.”
“No,” Jaxon said, holding up a hand. “Not tonight. Not like this.”
Mason raised an eyebrow. “Then how?”
Jaxon looked back at Ellie. She and Sophie were saying their goodbyes now, Ellie already pulling her jacket tighter, keys in hand.
“I talk to her,” Jaxon said. “Like a normal person.”
Mason laughed. “You?”
Jaxon shot him a look. “I’m serious.”
Evan’s mouth twitched. “That’s… surprisingly reasonable.”
“Two weeks,” Mason repeated. “You earn it. Ask her out. Publicly.”
“And if I don’t?” Jaxon asked.
“Then you lose,” Mason said. “Lunch for a month.”
Jaxon nodded once. “Fine.”
The bet settled heavy in the air, quieter than he expected. No cheering. No clapping. Just the crackle of the fire and the weight of a decision he already wasn’t sure about.
Ellie started toward her car.
Jaxon hesitated, then peeled away from the group.
Not to ask her out.
Not yet.
He caught up just as she reached her door.
“Hey,” he said.
Ellie turned, surprise flickering across her face—but not fear. Not annoyance.
“Hi,” she replied.
Her voice was steady. Curious.
“I, uh…” He cleared his throat. “Coach said you’re really good in English. You helped write that piece in the school paper, right?”
Her brows lifted slightly. “Yeah. I did.”
“It was good,” Jaxon said. “Really good.”
Ellie studied him, clearly unsure what to make of this. “Thanks.”
He nodded, suddenly hyper-aware of how stupid he probably looked. “Anyway. I just—yeah. See you around.”
He stepped back before he could say something wrong.
Ellie watched him for a second longer than necessary before opening her car door. “Goodnight, Jaxon.”
Hearing his name from her felt… different.
He walked away with his heart beating harder than it should’ve, Mason’s laughter distant behind him.
He hadn’t asked her out.
He hadn’t lied.
But as Jaxon Reed glanced back and saw Ellie glance back too—just once—he knew one thing for certain.
This bet was already more complicated than he’d planned.
He kept his head down as he crossed the gravel lot, the crunch of rocks under his sneakers grounding him more than the noise of the bonfire ever had. His chest still felt tight—like he’d just stepped off a ledge and hadn’t hit the ground yet.
Mason noticed first.
“Well?” he called, grin already pulling at his mouth. “Did you do it?”
Jaxon stopped in front of them, shoving his hands back into his jacket pockets. “No.”
Dylan blinked. “No?”
Mason scoffed. “Then what was that? You just… complimented her and bailed?”
“I talked to her,” Jaxon said. “That’s the point.”
Evan tilted his head. “You didn’t ask her out?”
“No.”
Mason laughed outright. “Wow. Brielle really did a number on you.”
Dylan frowned. “You said two weeks.”
“And I meant it,” Jaxon replied. “But I’m not doing it like that.”
Evan nodded slowly. “Smart.”
Mason rolled his eyes. “Since when do you care about timing?”
Jaxon thought of Ellie’s expression when he’d said her name. The way she’d looked at him like she was trying to figure him out instead of already having an answer ready.
“Since now,” he said.
The fire popped loudly behind them, sparks jumping into the night. Somewhere across the field, Brielle laughed again, but this time it didn’t sting the same way.
Mason crossed his arms. “So what’s the plan then?”
Jaxon hesitated only a second. “Tomorrow.”
Last Chapters
#116 Chapter 116 A pretty good life
Last Updated: 7/29/2026#115 Chapter 115 Proud Moment
Last Updated: 7/29/2026#114 Chapter 114 Partnership
Last Updated: 7/29/2026#113 Chapter 113 Write it down
Last Updated: 7/29/2026#112 Chapter 112 Two Hours
Last Updated: 7/28/2026#111 Chapter 111 Definitely His Daughter
Last Updated: 7/28/2026#110 Chapter 110 The Morning Of
Last Updated: 7/28/2026#109 Chapter 109 Let's Begin
Last Updated: 7/28/2026#108 Chapter 108 First day
Last Updated: 7/28/2026#107 Chapter 107 House Hunting
Last Updated: 7/28/2026
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