The film opens with Gary (Eben Moss-Bachrach), a tow truck driver, arriving at the home of Maddie Barker (Jennifer Lawrence) to repossess her car. In a desperate attempt to appeal to Gary's emotions, she reminds him of their past relationship that ended when she ghosted him, but her efforts are hilariously thwarted when another man she spent the night with stumbles out in his underwear. Despite Maddie's protests—it's crucial for her Uber driving job—Gary takes the car away, setting off a chain of chaotic events.
In an effort to retrieve her car, Maddie roller blades after Gary, only to stop when he stops at a diner for breakfast. Her attempts to lower the car from the tow truck are clumsy, leading to her arrest and subsequent probation. To make matters worse, she learns she owes a substantial amount in back taxes, jeopardizing her home.
Maddie earns her living as a bartender at a local waterfront spot in Montauk, where she works alongside her best friend Sara (Natalie Morales) and spends time with Sara’s husband Jim (Scott MacArthur). One day, after a confrontation with a rude customer, Sara shows Maddie a job listing from a wealthy family seeking someone to "date" their awkward teenage son Percy (Andrew Barth Feldman) before he heads off to college. Desperation leads Maddie to believe that participating in this dubious arrangement, which she realizes implies more than just dating, might be her best shot at financial salvation.
The following day, she roller blades to the Becker household, meeting Laird (Matthew Broderick) and Allison (Laura Benanti), who explain Percy’s shyness and lack of friends; he's more comfortable buried in video games than socializing. Although Maddie is significantly older than Percy—at 32 compared to his 19—she persuades Laird and Allison that she's suitable for the role. However, they insist that Percy must remain oblivious to their arrangement.
Maddie meets Percy at a dog shelter, using a form-fitting dress to seduce him under the pretense of adopting a dog. What follows is an awkward encounter where Percy, initially taken aback by Maddie's advances, ultimately reveals that he simply wishes to have a regular date, setting a comedic tone for their unconventional relationship.
Their attempts at a "romantic" outing are met with unexpected mishaps—such as a night on the beach where their clothes are stolen, leading Maddie to confront a trio of drunken teens. This encounter only exacerbates Percy’s fears about Maddie as she confronts the kids with surprising ferocity. The night spirals into chaos when a series of misunderstandings culminate in a high-speed getaway from the police, introducing further chaos to their burgeoning relationship.
As things develop, Maddie is seen trying to draw closer to Percy, leading to moments of vulnerability where both characters share past embarrassments and childhood struggles. Meanwhile, external pressures conjoin as a Realtor, Doug Kahn (Hasan Minhaj), suggests selling her house while Percy is showing signs of growth and interest in life beyond his gaming confines.
Maddie takes Percy on various escapades—arcades, fancy dinners, and unplanned adventures—where he surprises everyone by showcasing his piano skills. Just when their relationship reaches a pivotal point, a misunderstanding at a party leads to complications that threaten to derail everything they have built together.
Percy ends up devastated after overhearing a conversation about the arrangement, leading to a series of miscommunications and poor decisions, including an unfortunate encounter between Maddie and Percy that leaves them both reeling. Their paths diverge, with Maddie feeling isolated as her friends prepare to move away for new beginnings.
In an emotional climax, Maddie decides to sell her house, finding a bittersweet resolution that intertwines with her care for Percy. When she discovers he’s at a Princeton mixer, she confronts him one last time, leading to a reckoning amidst tumultuous circumstances. Their reconciliation is tender and heartfelt, culminating in a promise of support as Maddie transitions to a new chapter in California, revealing that she has adopted the former police dog, Milo, for Percy, ensuring they both have something to cherish as they move forward into their respective futures.
