Betting on You

Betting on You Plot Summary

Introduction

# From Enemies to Everything: A Love Story Built on Broken Walls The first time Bailey Mitchell wanted to strangle someone with their own boarding pass, she was seventeen and fleeing the wreckage of her parents' divorce at Fairbanks Airport. The target of her homicidal fantasies was Charlie Sampson—an arrogant boy who cut in line, made out with his girlfriend like the terminal was his personal bedroom, and spent their ten-hour flight to Nebraska explaining why love was a cosmic joke designed to destroy people. Three years later, fate revealed its twisted sense of humor when Bailey discovered her new coworker at Planet Funnn was the same insufferable boy who'd once declared her "labor-intensive" while dispensing his toxic wisdom about human nature. Now Charlie stood behind the garish entertainment complex's front desk, still devastatingly attractive, still armed with cutting sarcasm, but somehow different. The sharp edges of his cynicism had softened just enough to reveal glimpses of vulnerability beneath the armor. When Bailey's carefully planned Colorado getaway threatened to become a weekend trapped with her mother's new boyfriend, Charlie offered to play her fake boyfriend for three days. What began as a scheme to sabotage her mother's relationship became something far more dangerous—a journey through the messy territory between hatred and love, where two damaged people discovered that sometimes the person who drives you crazy is the same person who makes you whole.

Chapter 1: First Impressions: When Strangers Become Enemies

Bailey's hands trembled around her pink carry-on as she navigated Fairbanks Airport, the weight of her parents' separation crushing her chest like Alaska's winter sky. At seventeen, flying alone felt like stepping off a cliff into darkness. The security line stretched endlessly ahead, and that's when she encountered him—the boy who would haunt her thoughts for years. Charlie Sampson was making out with his girlfriend so aggressively that Bailey had to clear her throat twice before he bothered acknowledging her existence. When he finally opened one eye and glared at her while still attached to the girl's face, Bailey felt pure, concentrated rage flood her system. His "Mr. Nothing" t-shirt seemed prophetic—he was exactly that to her, nothing but trouble wrapped in teenage arrogance. The ten-hour flight became a masterclass in psychological torture. Charlie, with his dark hair and knowing smirk, seemed determined to dismantle every belief Bailey held about fairness and human decency. He mocked her vegetarian meal, her perfectly organized carry-on, her request for half-diet, half-regular Coke. When she ordered carefully, he declared her "labor-intensive" with the confidence of someone who'd solved a particularly challenging puzzle. "Guys and girls can't be friends," he announced with scientific certainty, as if he'd discovered a fundamental law of physics. "It's biologically impossible." Bailey wanted to argue, but something in his cynical certainty made her stomach twist. He spoke about relationships like someone who'd already been burned, despite being barely fifteen. When she pressed him about his own girlfriend, Charlie's face went carefully blank. "She'll figure it out," he said about their impending breakup, his casual cruelty taking Bailey's breath away. By the time they landed in Nebraska, Bailey had catalogued every infuriating thing about Charlie Sampson. His dismissive attitude toward her "precious" optimism, his ability to make her feel naive for believing in basic human decency, his toxic worldview that poisoned everything it touched. She promised herself she'd never see him again, never have to endure another moment of his presence. The universe, it seemed, had other plans entirely.

Chapter 2: Unlikely Allies: From Workplace Warfare to Reluctant Friendship

Two years later, Bailey spotted Charlie across her local movie theater lobby, and her heart performed an unwelcome gymnastics routine. He was taller now, broader through the shoulders, his boyish features sharpened into something dangerously attractive. The promposal poster behind him read "PROM?" in bold letters, and the petite blonde beside him was beaming like she'd won the lottery. Charlie's eyes found hers across the crowded space, that familiar smirk spreading across his face like he knew exactly how much he'd gotten under her skin during their flight. When they inevitably ended up in the concession line together, his first words were about her hair—how it was no longer the "poofy" disaster from the airport. "So you've evolved," he said, but his tone suggested evolution was somehow disappointing. "Our anniversary was last month," he said about the blonde, and Bailey couldn't hide her shock. This was the same boy who'd told her relationships were doomed to fail, that the odds of finding lasting love were worse than contracting a deadly disease. Now he was celebrating anniversaries and making elaborate promposals. "I've evolved," Charlie said with a shrug, but Bailey caught something hollow in his voice. The universe's sense of humor revealed itself fully when Bailey started her summer job at Planet Funnn. The entertainment complex was everything wrong with American capitalism—a garish monument to forced fun where employees wore space suits and maintained "intergalactic levels of happiness." She'd taken the job with her best friend Nekesa, expecting mindless work and easy money. She wasn't expecting Charlie Sampson to emerge from the training group, looking as surprised to see her as she was to see him. Three years after their first meeting, they were coworkers. The boy who'd once declared her "labor-intensive" was now her partner at the front desk, and Bailey discovered that proximity to Charlie was like exposure to a low-level toxin—dangerous in small doses, potentially lethal over time. Planet Funnn's front desk became a battlefield where Bailey and Charlie waged daily war through games and challenges. Charlie invented elaborate competitions—guessing customer snack purchases, racing to bathroom stalls during breaks, creating point systems for everything from complaints to coworker interactions. Bailey found herself drawn into his orbit despite every rational instinct screaming warnings.

Chapter 3: Colorado Confessions: When Fake Dating Feels Real

When Nekesa got grounded and couldn't make the Colorado trip, Bailey faced a weekend alone with her mother and Scott—her mother's boyfriend whose very presence threatened to upend her carefully guarded world. Scott was nice enough, but he represented everything Bailey feared about change, about losing the careful equilibrium she and her mother had built after the divorce. The idea of watching him teach her to ski, of pretending to be a happy blended family, made her want to disappear. Charlie's offer to take Nekesa's place should have been immediately rejected. Instead, Bailey found herself saying yes to not just the trip, but to an elaborate charade. Fake dating Charlie for the weekend would add tension to her mother's romantic getaway, potentially slowing down Scott's integration into their lives. It was manipulative and immature, exactly the kind of scheme Bailey would normally reject on moral grounds. But Charlie made it sound like an adventure instead of a deception. "We'll show up holding hands and watch Scott's head explode in real time," he said, his eyes dancing with mischief. "It'll be beautiful." The way he said it—like they were planning a harmless prank instead of emotional warfare—made Bailey feel brave in a way she'd never experienced. The eight-hour drive to Colorado became a masterclass in Charlie's complexity. He sang along to Taylor Swift with surprising enthusiasm, shared elaborate theories about gas station snack hierarchies, and revealed unexpected vulnerability when his car keys fell into a urinal and he couldn't retrieve them himself. Bailey fished them out without question, recognizing the shame in his eyes and choosing kindness over curiosity. When they finally reached Breckenridge, the mountain town twinkling with fairy lights against the dark sky, Bailey felt like she was stepping into a different version of herself. Charlie squeezed her hand as they approached the condo, and Bailey realized the most dangerous part of their plan wasn't deceiving Scott—it was how natural it felt to have Charlie's fingers intertwined with hers. The explosion, when it came, was everything they'd hoped for. Scott's face went through a spectrum of emotions—surprise, anger, resignation, and finally grim determination to salvage his romantic weekend. Bailey's mother was furious at the deception but trapped by the logistics of having Charlie already there. The battle lines were drawn, and Bailey found herself on Charlie's side of a war she'd started but wasn't sure she could win.

Chapter 4: Walls Come Down: Vulnerability in a Blanket Fort

The condo became a pressure cooker of forced civility and simmering tensions. Scott tried to maintain his role as gracious host while clearly wanting to throttle Charlie with his bare hands. Bailey's mother oscillated between anger at her daughter's manipulation and grudging appreciation for Charlie's unexpected helpfulness—he cooked elaborate meals, cleaned without being asked, and charmed her with his encyclopedic knowledge of football statistics. Charlie played the devoted boyfriend with theatrical flair, holding Bailey's hand during dinner, brushing imaginary lint from her sweater, calling her "babe" with just enough sincerity to make Scott's eye twitch. But Bailey began to notice when his performance slipped—the way his jaw tightened at Scott's pointed comments about "young men who don't respect boundaries," the careful distance he maintained even while playing affectionate. When a confused goose crashed through her bedroom window in the middle of the night, Bailey found herself relocated to the living room where Charlie was camping on the pullout sofa. The sight of him in heart-patterned pajama pants that were four inches too short—a gift from his little sister—made something tender unfurl in Bailey's chest. "They're incredibly sexy," she teased, and Charlie struck a pose that made her laugh until her sides hurt. Later, as they lay in darkness watching New Girl reruns, the conversation turned serious. Charlie talked about his mother's pregnancy, the way his family was expanding in directions that didn't include him. His voice carried a loneliness that made Bailey want to reach across the space between them and offer comfort. "I feel like I'm disappearing," he said quietly, and Bailey understood exactly what he meant. The shift happened gradually, then all at once. Bailey began to notice things about Charlie that had nothing to do with their fake relationship—the way he unconsciously reached for antacids when stressed, his habit of running hands through his hair when thinking, the genuine warmth in his voice when he talked to her mother about football. He was performing the role of boyfriend, but the kindness underneath felt real. Their most dangerous moment came during their last evening in Colorado. At the local brewery, surrounded by college students and ski instructors, they found a corner table where they could watch the crowd without being watched themselves. For the first time all weekend, they weren't performing for anyone. "Can I ask you something?" Bailey said. "Why did you really agree to come on this trip?" Charlie was quiet for so long she thought he wouldn't answer. When he finally spoke, his voice was different—softer, more honest than she'd ever heard it. "Because you asked me to," he said simply. "And because I wanted to spend time with you without having to pretend I didn't."

Chapter 5: Trust Shattered: The Bet That Broke Everything

The return to Nebraska brought reality crashing back with brutal efficiency. Planet Funnn felt smaller after the mountain air, the fluorescent lights harsh after Colorado's golden sunsets. Bailey and Charlie fell back into their routine of front desk banter and elaborate games, but something fundamental had shifted between them. The easy antagonism was still there, but underneath ran a current of awareness that made every interaction feel loaded with possibility. Charlie's ex-girlfriend Becca had apparently noticed his improved mood and was making overtures about "staying friends." Bailey watched him check his phone obsessively, saw the way his face would close off when Becca's name appeared on the screen. "She wants to be friends," he told Bailey one afternoon, his voice carefully neutral. "Says there's no reason we can't stay in touch." Bailey wanted to shake him, to point out that Becca's sudden interest coincided suspiciously with his apparent recovery from their breakup. The crisis came when Charlie's mother announced her engagement via text message while he and Bailey were working the evening shift. Bailey watched his face go carefully blank in the way she'd learned to recognize as his defense against overwhelming emotion. "Congratulations," Bailey said quietly, and Charlie's laugh was bitter enough to etch glass. "Yeah. Congratulations to me on getting a new stepdad and a baby sibling all in one year." The pain in his voice was so raw that Bailey abandoned her post and pulled him into the supply closet, where he could fall apart without an audience. "I'm losing everything," he said, and Bailey understood he wasn't just talking about his family. He was talking about the careful distance he'd maintained from everyone, the cynicism that had protected him from exactly this kind of pain. He was talking about her, and the way she'd slipped past his defenses when he wasn't looking. But the real devastation came later, outside an Applebee's where their friends had gathered to celebrate birthdays that felt like funerals. Theo's voice cut through the autumn air with surgical precision, revealing the bet Charlie had made months earlier—a wager about whether he could "get" Bailey, as if she were a prize to be won rather than a person to be cherished. The words hit Bailey like physical blows, each revelation stripping away another layer of trust she'd built around Charlie's character. Every moment they'd shared—the coffee runs, the late-night conversations, the kisses that had felt like coming home—suddenly looked different through the lens of manipulation. Had any of it been real, or had she been nothing more than a challenge to be conquered?

Chapter 6: Finding Courage: Second Chances and Honest Hearts

The formal dress hung in Bailey's closet like a promise she wasn't sure she wanted to keep. Fall formal loomed ahead, a night that should have been magical but felt instead like an obligation to be endured. Nekesa had forgiven her after learning the full truth about the bets, but their friendship bore new scars, tender places that ached when touched by memory. Bailey's world had shifted in other ways too. Moving into Scott's house had been less traumatic than expected, his kindness and understanding slowly eroding her resistance. Her father had started calling again, their conversations awkward but genuine, like learning to speak a language they'd both forgotten. Change, it seemed, didn't always mean loss—sometimes it meant growth, even when that growth came wrapped in pain. The night of the dance found Bailey sitting alone at a table, watching her friends spin across the floor in the arms of people who loved them. Nekesa and Aaron had reconciled in spectacular fashion, their reunion a testament to the power of honest communication. Even her other friends seemed lost in their own perfect bubbles, leaving Bailey to contemplate the ways love could bloom when people were brave enough to tend it. Zack's appearance at her table should have been the moment she'd been waiting months to experience. He was newly single, still beautiful, still kind—everything she'd thought she wanted. But as he spoke, Bailey felt nothing but mild fondness, the desperate longing she'd carried for him revealed as nothing more than nostalgia for a simpler time. Her heart, it seemed, had already chosen its path, even if her mind was still catching up. The last song played as Bailey made her escape, Taylor Swift's "The Last Time" following her into the lobby like an accusation. She was fumbling for her phone to call an Uber when she heard a commotion near the entrance—security guards blocking someone's path, voices raised in frustration and desperation. Charlie stood in the doorway like a vision from her dreams, wearing a black suit that made him look older, more serious, but no less beautiful. His hair was disheveled, his face flushed with emotion, and when their eyes met across the lobby, Bailey felt her carefully constructed walls begin to crumble. He'd come for her, fought his way past security and his own fears to find her. When a tiny cat head emerged from Charlie's jacket—his beloved Puffball, smuggled in as a gesture so absurd and touching it defied explanation—Bailey felt the last of her resistance melt away.

Chapter 7: Choosing Love: From Broken Trust to Forever

The conversation that followed was raw and honest, Charlie's words tumbling out like confessions at a revival meeting. He spoke of missing her, of the bet meaning nothing compared to what they'd built together, of love he'd been too afraid to name until it was almost too late. The bet, he insisted, had been meaningless—a throwaway comment made before he'd known her heart, before she'd become the center of his universe. Bailey listened with tears in her eyes, recognizing the truth in his voice even as part of her remained afraid. They'd hurt each other badly, trust broken and rebuilt in the space of a single conversation. But love, she was learning, wasn't about perfection—it was about choosing each other again and again, even when that choice required courage neither of them was sure they possessed. The kiss outside the convention center tasted like forgiveness and new beginnings, Charlie's mouth moving against Bailey's with desperate relief. They'd found their way back to each other through the wreckage of pride and fear, two people who'd learned that love wasn't a weakness to be avoided but a strength to be embraced. The autumn air swirled around them like a blessing as they held each other close, Puffball purring between them like a furry seal of approval. The months that followed were a masterclass in the art of rebuilding. They took things slowly, learning to be friends again before they could be lovers, discovering that their connection ran deeper than attraction or convenience. Charlie met Bailey's father during a video call that left both men awkward but hopeful, while Bailey slowly warmed to the chaos of Charlie's fractured family. Scott and Bailey's mother married in a ceremony at Planet Funnn, the venue chosen for its sentimental value and employee discount. Bailey stood beside her mother in a dress Charlie had helped her pick, watching two people choose love despite its complications. Charlie's commentary during the ceremony was inappropriate and perfect, his whispered jokes keeping Bailey grounded as her world shifted once again. The reception became a celebration of more than just her mother's happiness. Bailey danced with Charlie to Ed Sheeran songs, their bodies moving together like they'd been designed for this moment. When he whispered that he loved her, the words felt like coming home after a long journey through foreign territory. She said them back without hesitation, finally brave enough to claim the happiness that had been waiting for her all along.

Summary

In the end, Bailey Mitchell learned that some stories begin with endings—the end of childhood certainties, the end of emotional safety, the end of believing that love was something that happened to other people. Her journey from the fluorescent-lit misery of Fairbanks Airport to the warm embrace of chosen family was marked by false starts and genuine revelations, by the kind of messy, complicated growth that defines the passage from adolescence to something approaching wisdom. Charlie Sampson discovered that his carefully constructed philosophy of emotional detachment was nothing more than fear dressed up as sophistication. The boy who'd worn "Mr. Nothing" like armor learned that vulnerability wasn't weakness but the only path to the connection he'd been craving all along. Together, they proved that sometimes the person who drives you crazy is the same person who makes you whole, that love isn't about finding someone perfect but about choosing to see perfection in someone real. Their story continues beyond the final page, in the small moments that make up a life shared—morning coffee and late-night conversations, rescued cats and blended families, the daily choice to love someone even when they leave their socks on the floor or eat the last piece of pizza.

About Author

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Lynn Painter

Painter reframes the romantic comedy genre by emphasizing humor and heartfelt plots, making her work appealing to a wide range of readers. Her focus on creating lighthearted and entertaining narratives, evident in titles such as "Mr. Wrong Number" and "The Love Wager", reflects her affinity for stories filled with wit and optimism. Whereas she initially struggled with other genres, a pivotal suggestion from her agent to concentrate on rom-coms allowed Painter to thrive in a field that aligns with her personal interests.\n\nHer writing method, which includes conversational style and relatable characters, not only engages readers but also offers an escape through comedic and romantic challenges. Painter extends her creative reach beyond novels by contributing to the "Omaha World-Herald", particularly in the parenting section, providing a community-centered perspective. This approach ensures her stories resonate with audiences who appreciate humor infused with real-life themes.\n\nFor readers seeking light escapism, Painter's novels offer a blend of humor and romance, making them a favorite in the romantic comedy book market. Her status as a "New York Times" bestselling author underscores her commercial success and influence, as seen in her popular book "Better Than the Movies". With her works capturing the essence of romantic storytelling, Painter’s unique voice and engaging narratives continue to captivate and entertain her audience.

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