The Love Wager

The Love Wager Plot Summary

Introduction

The scent of Crown Royal and poor decisions hung heavy in the hotel kitchen as Hallie Piper sat cross-legged on a stainless steel counter, watching a stranger pour whiskey into two shot glasses. She'd just witnessed the most spectacular wedding meltdown in recent memory—a jealous girlfriend throwing wine, an engagement ring revealed in fury, and a groom declaring he wouldn't marry his psychotic bride. Now here she was, the bartender who'd accidentally orchestrated the whole disaster, about to get drunk with the best man whose proposal had just imploded. Jack Marshall should have been celebrating his sister's wedding. Instead, he was drowning his sorrows with a redhead who had somehow managed to expose his girlfriend's true nature in under ten minutes. Vanessa was gone, the ring was back in his pocket, and he was strangely grateful to this sharp-tongued woman who'd called his ex a jealous psycho to her face. As they raised their glasses in the empty kitchen, neither realized they were toasting the beginning of something that would completely upend their carefully ordered lives. What started as commiseration would become competition, friendship would blur into something more dangerous, and a simple bet would force them both to confront the difference between wanting love and actually finding it.

Chapter 1: A Night to Remember: The Wedding Encounter

The wine hit Hallie's face like a cold slap of reality. She blinked, tasting chardonnay on her lips as Vanessa's perfectly manicured hand trembled with rage. The blonde had just thrown an entire glass of wine at her face because Jack—the impossibly handsome groomsman—had been explaining why he'd bought an engagement ring that morning. "You're proposing?" Vanessa had shrieked, her face transforming from fury to sunlight. Jack stared at her with narrowed eyes for five solid seconds before delivering the kiss of death: "I'm not now." The hotel ballroom buzzed with four hundred wedding guests, but all Hallie could focus on was the disaster unfolding at her bar. She wiped wine from her face with a towel, watching Jack's jaw flex as he processed what his girlfriend had just done. Vanessa looked like she wanted to throw something else, but Jack was already grabbing her arm. "We need to go," he said through gritted teeth. Hours later, Hallie found herself in the hotel kitchen with the same man, both of them holding bottles of Crown Royal like lifelines. Jack had discarded his jacket and rolled up his sleeves, revealing forearms that belonged in a cologne advertisement. His dark hair was disheveled, his tie hung loose around his neck, and his blue eyes carried the particular weariness of a man who'd just dodged a bullet. "So you got me dumped," he said, settling onto the counter beside her, "so now it's your job to get me drunk." "I had nothing to do with your relationship imploding," Hallie shot back, though she took the bottle when he offered it. "I think you actually owe me a thank-you." "For what?" "For saving you from a lifetime with a jealous psycho." They drank straight from the bottle, trading stories and sarcastic observations about love, marriage, and the spectacular ways relationships could self-destruct. Jack was funnier than she'd expected, with a dry wit that matched her own cynicism. When he described Vanessa's reaction to his father's dog licking her hand—"She said ewwww like the poor thing had the plague"—Hallie nearly choked on her whiskey. The alcohol loosened their tongues and lowered their guards. Jack told her about feeling lonely despite being surrounded by people, about rushing into a relationship because he was tired of being alone. Hallie confided her own relationship disasters, her year-long dating sabbatical after Ben had destroyed her heart by telling her he loved the idea of her but not the actual her. By the time they stumbled upstairs, they were both drunk on whiskey and the dangerous intimacy that comes from shared trauma. The elevator ride was a blur of heated kisses and fumbling hands, Jack pressing her against the wall as she hit the stop button with more boldness than she'd felt in years. His hotel room became a tangle of discarded formal wear and desperate touches, two people seeking comfort in the oldest way possible. When morning came, Hallie woke up sideways at the foot of the bed, fully clothed except for her missing bra. Jack lay sleeping at the headboard, and she could see her undergarment tangled in the sheets beneath him. Rather than wake him, she crawled commando-style across the carpet, grabbed her clothes, and fled before he could open his eyes.

Chapter 2: The Wager: A Competition for Love

Months passed before Hallie encountered Jack again—this time through a dating app called Looking4TheReal. She'd finally decided to end her self-imposed romantic exile, encouraged by her best friend Chuck's success in finding love through online dating. Her finger hovered over Jack's profile photo, taken at his sister's wedding in the same tux he'd worn the night they'd demolished a bottle of Crown Royal together. Unable to resist messing with him, she sent a message: "Hey, Jack, it's Hallie, the bartender from your sister's wedding! Why haven't you called? I really thought we connected." His response was immediate and panicked: "Hey there, Hallie. I had a lot of fun with you after the wedding, and you seem like a cool person." "God, Jack, relax," she typed back. "I DO NOT WANT TO DATE YOU. I saw your profile when I was shopping for soul mates and thought it would be fun to give you a heart attack." What followed was an honest conversation that surprised them both. Jack admitted he was seriously looking for someone significant, tired of casual relationships that went nowhere. Hallie confessed she wanted the same thing—someone who liked her more than anyone else in the world, her favorite human, the person she'd dying to tell when anything happened. "It sounds like you want to marry your best friend," Jack observed. "I literally do." They were both tired of dating apps and awkward first dates, both craving something real in a world of swipe-right superficiality. That's when Jack proposed the wager that would change everything. "Who finds it first," he challenged. "Who finds their person first." The prizes were tantalizing: Jack offered his frequent flyer miles and five nights at any hotel if Hallie won. In exchange, she dangled a Cubs World Series baseball signed by the entire 2016 team—something that would make Jack's father cry with joy and cement Jack as the favorite son. "I already hate this app and blind dates," Jack admitted. "But if there's a fun incentive, and I'm in it with someone else, it might not feel like an endless, depressing chore." They shook on it virtually, two people who'd shared one perfect night of temporary insanity now committed to helping each other find lasting love. Neither acknowledged the irony that they were both describing exactly what they'd found in each other—the person they couldn't wait to text when something funny or awful or wonderful happened.

Chapter 3: Partners in Crime: Dating Support System

Their post-date meetings at Taco Hut became ritual. Jack would text location details, Hallie would order chicken tacos with cheese on the bottom ("What's the point of cold, hard cheese?" Jack agreed), and they'd dissect their romantic disasters over cheap beer and excellent nachos. Jack's dates were a parade of women who either wanted too much too fast or seemed to have no personality at all. There was Kayla, the PhD candidate who wanted to be "treated like a queen," complete with gifts, deference, and his complete devotion. Another woman spent their entire dinner listing her food allergies in excruciating detail. A third one answered his getting-to-know-you questions like she was in a job interview, offering no conversation in return. Hallie's dating life was equally disastrous. Stephen the dentist seemed perfect until he started crying over his divorce—from his ex-wife, with whom he'd had to split custody of their "twin" Labradoodles. Kyle, a diesel mechanic, immediately asked her to do his taxes and got offended when she declined, calling her stuck-up for not needing side money. "Rich enough to not have to do my blind date's taxes," Hallie had snapped, regretting it immediately when Kyle's face turned red with embarrassment. Their friendship deepened through shared disappointment. Jack helped Hallie move into her first solo apartment, hauling her bed and dresser up three flights of stairs while she directed traffic and provided commentary. They watched Pride and Prejudice on her living room floor, debating whether the best romantic moment was Darcy's smile at Pemberley or the almost-kiss in the rain. "You're kind of a hopeless romantic," Hallie observed, and Jack's response revealed more than he intended: "It's too devastating when they pull back." When Hallie adopted Tigger, an enormous orange tabby with anger management issues, Jack was there to help wrestle the furious feline into his carrier. The cat immediately loved Jack and barely tolerated everyone else, a fact that both amused and touched Hallie more than she wanted to admit. Their text conversations became the highlight of both their days—rapid-fire exchanges of observations, jokes, and honest confessions about their dating failures. They developed their own language, reviving the country conjunction "n'" and creating increasingly ridiculous euphemisms for sex that made them both laugh until their sides hurt. "Getting your parts jostled?" Jack suggested. "Are you going in for your annual checkup or having sex?" Hallie shot back. Neither would admit that their friendship had become more important than their dating success, that they looked forward to their Taco Hut debriefs more than the actual dates.

Chapter 4: Playing Pretend: The Vail Wedding Weekend

The call came at the worst possible moment. Hallie had finally found someone promising—Alex, a real estate agent who was funny, charming, and seemed genuinely interested in her. They'd been dating for weeks, sharing perfect kisses and meaningful conversations. She'd even invited him to her sister's destination wedding in Vail, ready to introduce him as her boyfriend. Then Alex dumped her over the phone. "You seem really great, but I don't think this is going to work," he said, his voice thick with something she couldn't identify. "Some guy is going to be really lucky, because you're an awesome girl, but I just don't think I'm that guy." Hallie cried until her eyes were swollen, devastated not just by the rejection but by the timing. Her perfect sister Lillie was marrying Riley Harper in a fairy-tale mountain wedding, and Hallie would have to face it alone. Worse, her ex-boyfriend Ben would be in the wedding party, the same Ben who'd destroyed her by saying he loved the idea of her but not the actual her. That's when Jack appeared at her door with tissues and the solution that would save her pride and destroy her peace of mind. "If you want, I'll go with you," he offered casually. "You can pretend I'm your boyfriend, and we can be the greatest fucking couple they've ever seen until we return home from the trip and break up." The lie came together perfectly. They'd met at his sister's wedding, reconnected on the dating app, been going on taco dates ever since. Jack had frequent flyer miles to upgrade them to first class, a truck to help her move, and the acting ability to pull off being head-over-heels in love with her. "From the second we enter the airport to depart until the moment we return home," he promised, "I will be head-over-heels, worship-the-ground-you-walk-on, wildly obsessed and madly in love with you." The words sent an unexpected thrill through her, even though she knew they were just part of the performance. What she didn't expect was how naturally the pretense would come, or how dangerous it would feel when Jack's hand slipped into hers at airport security and stayed there.

Chapter 5: Blurred Lines: When Fake Feelings Turn Real

The only-one-bed situation at the resort should have been awkward. Instead, it became the most intimate non-sexual experience of Hallie's life. They shared midnight room service french fries while watching New Girl reruns, debating character rankings and feeding each other ketchup-dipped fries. Jack brushed his teeth beside her in the bathroom mirror, and she fell asleep to the sound of his quiet breathing inches away. The wedding weekend became a masterclass in method acting. Jack's hand found the small of her back during the rehearsal dinner, guiding her through conversations with relatives she barely remembered. He zipped her bridesmaid dress with fingers that lingered on her spine, making her breath catch. When she got hiccups during the ceremony, his eyes never left her face, his expression soft with the kind of affection that looked disturbingly real. "The way your boyfriend watches you is disgusting," whispered Carolyn, the maid of honor. "I want to vomit with jealousy." Their fake relationship had rules—no sex, just enough physical affection to sell the illusion. But the rules began cracking during their first kiss at airport security, when Jack's mouth claimed hers with an intensity that made her knees buckle. They cracked further when he carried her piggyback through muddy sidewalks, his cologne surrounding her as she buried her cold nose in his warm neck. The breaking point came in a supply closet during the rehearsal dinner, when Jack kissed her forehead and said quietly, "Jack and Hallie for real, before things go back to normal." What followed was the kind of kiss that rewrote definitions. Not the desperate, alcohol-fueled collision from their first night, but something deeper—intimate and sexual and tender all at once. Jack's hands framed her face like she was precious, his mouth moving over hers with a reverence that made her dizzy. "Don't you dare stop," she breathed against his lips. "I have to, Hal," he panted into her neck. "Before we mess up everything." When a housekeeper opened the door and sent them tumbling onto the lobby floor in a tangle of limbs and smudged lipstick, they couldn't stop laughing. That's when Hallie knew with terrifying clarity that she was in love with her fake boyfriend, and their carefully constructed pretense was about to destroy them both.

Chapter 6: Broken Connection: Misunderstandings and Separation

The end came swiftly after they returned home, triggered by a chance encounter that unraveled everything. At the airport, Hallie ran into Alex—the same Alex who'd broken her heart just days before their trip. He wanted to apologize, to explain, to maybe try again. "Your friend told me about the bet," Alex said, and Hallie's blood turned cold. Jack had told Alex about their wager during a casual parking lot conversation, mentioned it as proof that fate hadn't brought Alex and Hallie together. The revelation hit her like a physical blow—Jack had sabotaged her relationship, then comforted her when Alex inevitably broke up with her. "I got the impression he was trying to make something happen with you, and I was in the way," Alex continued, oblivious to the devastation his words were causing. Back in her apartment, Hallie confronted Jack with barely contained fury. She'd figured it out—he'd been lonely after his uncle's death and his best friend's marriage, desperate enough to destroy her relationship so he could have his comfortable fallback option. "Why didn't you tell me that you told him about the bet?" she demanded. Jack's face went carefully blank. "It wasn't like that at all. I just told him about the bet because that jackass thought fate brought you two together." "And it was like that, Jack, because you're wholly responsible for him breaking up with me." The accusation hung between them like poison. Jack couldn't deny it, couldn't explain that he'd acted out of jealousy and fear of losing her to someone else. Instead, he watched her face close off, watched her decide he was just another man who'd disappointed her. They had sex one last time—desperate, angry, heartbreaking sex that felt like goodbye. Hallie called it their "last night of pretend," and Jack's heart shattered at the clinical way she dismissed what had become the most real thing in his life. "Let me get this straight," he said, his voice rough with hurt. "That whole fake dating game is over and we're back to being friends, but you want to fuck one last time?" When it was over, when she'd used him for one final night of physical comfort, she made it clear their romantic experiment was finished. Jack left without a fight, too proud to beg and too hurt to explain that he'd fallen in love with his fake girlfriend somewhere between the airport security line and the Colorado mountains. Two weeks of silence followed, two weeks that felt like years.

Chapter 7: Coming Home: Confessions in the Rain

The rain was torrential the night Jack finally found his courage, sheets of water turning the downtown streets into rivers. He'd been watching Hallie through the restaurant window, seeing her smile at Alex over dinner, and he couldn't take another moment of uncertainty. When she followed him outside, her hair immediately soaking, her face fierce with anger, he knew this was his last chance to tell the truth. "Where do you think you're going?" she yelled through the downpour. "You're just bailing?" "You didn't look like you needed my help," he shouted back. "What 'us' is there?" she demanded when he mentioned wanting to talk about them. "I haven't heard from you in weeks, and now you think you have a right to say the word 'us'?" The accusation in her voice broke something loose in his chest. Two weeks of missing her, of driving past every place that reminded him of her, of lying awake remembering the sound of her laugh—it all came pouring out. "Why didn't you at least text me?" Her voice cracked, revealing the hurt beneath her anger. "How could you just leave me all alone?" Standing there in the rain, soaked and shivering and more beautiful than any woman had a right to be, Hallie looked like everything he'd never known he wanted. The words came out wrong—he said he thought he was in love with her instead of declaring it with certainty—but she heard the truth underneath his clumsy phrasing. "That is a terrible thing to say, you dick," she shot back, and he realized his mistake. "You didn't tell me you love me, you said you 'think' you're in love with me," she continued, her teeth chattering. "Who do you think you are—Darcy in the rain, telling Elizabeth that he loves her in spite of her inferior birth?" The Pride and Prejudice reference made him smile despite everything, because only Hallie would argue about his declaration of love using Jane Austen metaphors. She was calling him Mr. Darcy, which meant she was Elizabeth Bennet, which meant this was the scene where everything was supposed to work out. "I knew I was in love with you the minute you fell out of the stupid closet at the rehearsal dinner," she admitted, and his heart stopped. "It didn't take me a fucking fortnight to get to 'possibly.'" The kiss that followed tasted like rain and second chances. Her lips were cold, her body warm against his, and when she melted into him with a sigh that sounded like coming home, Jack knew he'd found what he'd been searching for his whole life. They took shelter under an awning, and he tried again—better this time, with words that came from his heart instead of his fear. "Forgive me for not wanting to put a label on my feelings, but I don't know shit about love, okay? All I know is that you've ruined every single thing about my life." She looked skeptical until he explained—how he couldn't drive past Burger King without thinking of her, couldn't hear a British accent without remembering her terrible impressions, couldn't see his phone buzz without hoping it was her ridiculous texts. "Everything in my life was fine before," he said, "but now it's so different and I hate it." "I hate it, too," she whispered, stepping closer. When he told her he missed her so much he could hardly breathe, when he promised he was so in love with her and that she was the first person he wanted to tell when anything happened, she laughed through her tears and asked if their "its" had gotten switched—if he'd become the one who needed someone who liked him more than anyone else in the world. "Well, that would mean that you feel like I complete you," he said, remembering their conversation about what they were each looking for. She raised her chin, looked into his eyes, and gave him the answer that changed everything: "Yeah, it would."

Summary

Standing in the rain outside Taco Hut six months later, Jack and Hallie could barely remember why they'd thought finding love would be so difficult. Their bet had been declared a tie—they'd found their person at exactly the same time, though it had taken them longer than expected to realize it. Jack got his Cubs baseball for his father, Hallie got her vacation miles, and they both got something infinitely more valuable: the person who made every ordinary moment feel like an adventure. Their wedding planning involved debates over whether to have the ceremony at Taco Hut (Hallie's suggestion) or somewhere slightly more traditional (Jack's counter-proposal). They compromised on a venue that served decent mexican food and allowed them to write their own vows, which included promises to always order cheese on the bottom and never use terrible euphemisms for sex in public. The only real argument was over whether Jack's middle name—Alan, after the country singer—should be included in the ceremony, a detail that made Hallie laugh so hard she nearly choked on her engagement ring. What had started as a wager between friends became proof that sometimes the best love stories begin with the worst first impressions, that real intimacy grows from shared laughter over terrible dates and midnight french fries, and that the person you're meant to be with might be the one you'd never considered dating—until you couldn't imagine life without them. Jack and Hallie had spent so much time looking for their perfect match that they'd almost missed the fact that they'd already found each other, disguised as the friend who always knew exactly what to say when everything else went wrong.

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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