Maddie Barker, portrayed by Jennifer Lawrence, lives a challenging life in Montauk, where she works as a bartender and relies heavily on her Uber job to make ends meet. Her life takes an unexpected turn when a tow truck driver named Gary, played by Eben Moss-Bachrach, arrives at her home to tow her car. Maddie, emphasizing her past relationship with Gary, tries to persuade him to reconsider, but her efforts are thwarted when another man she was with earlier that night appears in his underwear and gropes her in an attempt to assert his own dominance. Despite her protests and attempts to delay the process, Gary proceeds to tow her car away, leaving Maddie stranded and frustrated.
Determined to catch up to Gary, Maddie rollerblades through the streets until she reaches his truck. When she tries to free her car, a clumsy struggle ensues, resulting in her being placed on probation and facing significant back taxes that threaten her home. Maddie, a native of Montauk, has always lived in the same place, inserting a personal backdrop of familiarity and nostalgia into her story. She spends her days managing her attitude at work, often clashing with customers, and her nights hanging out with her close friend Sara, played by [Natalie Morales], and her husband Jim.
In a moment of desperation, Maddie stumbles upon a job listing from a wealthy family, seeking someone to "date" their son Percy, played by [Andrew Barth Feldman], before he heads off to Princeton University. The catch is that "dating" is a euphemism for sex, but Maddie, seeing it as her chance for financial stability and to save her house, decides to accept the job. She visits the Becker family and meets Percy’s parents, Laird, portrayed by [Matthew Broderick], and Allison, played by [Laura Benanti]. They discuss their son Percy, who is shy, awkward, and spends much of his time playing video games in his room, away from social interactions. Although Maddie is 32 and Percy is only 19, she convinces them she’s the right person for the job, with the condition that Percy must not find out the true nature of their arrangement.
Maddie is tasked with finding Percy at a local dog shelter, where she employs her charm, wearing a fashionable dress to seduce him while pretending to want to adopt a dog. Percy introduces her to a former police dog named Milo, who was discharged from the force for cocaine addiction, adding to his complexity. His nervousness increases as Maddie’s advances become more aggressive, leading her to borrow Jim’s van and take Percy to her house. However, Percy, feeling uncomfortable, pulls out a can of mace and sprays her, revealing his own insecurities. Maddie, painfully honest, admits she was attracted to him, and after a tense moment, Percy expresses a desire to go on a proper date, which Maddie agrees to despite her reservations.
Their relationship develops further as Maddie takes Percy to a local bar, where she introduces him to her friend Sara and tries to help him relax, despite his dislike for the Long Island iced tea he is offered. Tragedy strikes when a man named Travis, played by [Quincy Dunn-Baker], who used to date Maddie, appears and warns Percy about getting too close to her, hinting at her complicated past. Despite the tension, Maddie and Percy share a fun and rebellious day at the beach, where Maddie persuades Percy to skinny-dip. Their adventure leads to chaos when drunk teens show up, steal their clothes—including wallets, phones, and keys—and Maddie, undressed, fights off the teens to retrieve their belongings. The cops arrive, but Maddie’s quick thinking and driving skills help them avoid trouble, even if it means risking her license.
As their relationship deepens, Maddie attempts to seduce Percy again, this time noticing a rash on his back which he attributes to anxiety. They share vulnerable moments, including Maddie’s own embarrassing memories and Percy's troubled history with classmates who spread rumors about him sleeping in his parents’ bed. One night, after a series of outings and conversations, Maddie and Percy go out for a dinner at a fancy restaurant to make up for missed prom experiences. Percy impresses everyone by playing “Maneater” on the piano, earning cheers and applause. During the evening, Natalie, a girl from Percy’s school, approaches him, making Maddie uneasy as she learns about their plans to attend Princeton together.
Their night ends at a Princeton-bound students’ party, where Maddie’s fears are realized when she finds Percy in bed with Natalie, both clearly intoxicated. Percy, unable to handle his feelings, confesses his love for Maddie, and they share a tense moment. However, Maddie refuses to be intimate with Percy in his drunken state, understanding the importance of genuine connection. Meanwhile, Percy's parents notice his change in personality and behavior, which they attribute to his new relationship with Maddie. They decide that Maddie can keep the car without continuing their arrangement, but Percy, overhearing their conversation, becomes heartbroken, feeling betrayed.
Percy’s growing attachment to Maddie leads him to make reckless decisions, including crashing his parents’ car into a tree with Maddie and her new co-worker, Crispin, causing chaos. Ultimately, Maddie and Percy try to get closer again, culminating in a moment where they decide to finally have sex. Yet, it is awkward and disappointing when Percy ejaculates prematurely, revealing his fears and insecurities. Distressed, he admits he doesn’t want to see Maddie anymore, believing she belongs in Montauk forever.
Despite this, Maddie remains determined. She sells her house, originally owned by her father, to Jim and Sara, who plan to move to Florida for their growing family. Maddie, with renewed resolve, prepares to move to California. Her attempt to reconcile with Percy proves difficult, as he continues to retreat into his world of video games and silence. Maddie finds him at a Princeton mixer, trying to explain herself as he stubbornly refuses to speak. Their emotional reconciliation occurs when Maddie hops onto the hood of his car, and Percy drives her along the beach, where they share a tearful apology and a heartfelt farewell.
In the end, Percy goes to Princeton, while Maddie departs for California, knowing she made the right choice. She surprises him by bringing home Milo, the dog, symbolizing new beginnings. Their relationship, marked by mistakes and growth, underscores themes of love, independence, and self-discovery, leaving both with the hope of brighter futures ahead.
