The film kicks off with a rather intriguing encounter between Gary, a tow truck driver, and Maddie Barker, the woman whose car he's come to haul away. Their past relationship adds an emotional layer to Maddie's desperation, as she pleads with Gary to reconsider, especially since her car is crucial for her job as an Uber driver. Unfortunately for Maddie, her attempts are thwarted when another man, a casual fling from the night before, unexpectedly emerges in his underwear, further complicating her appeals and leaving Gary no choice but to haul her car away.
Determined to reclaim some semblance of control over her life, Maddie chases after Gary on rollerblades, only to embarrassingly fail to detach her vehicle from his tow truck at a diner. Her antics result in an arrest and the added stress of back taxes threatening her home. As the story unravels, we see Maddie managing a bartending job at a local waterfront bar in Montauk, where she spends her days working alongside her best friend Sara and her husband Jim. One day, during a break, Sara unveils an unusual job posting from a wealthy family seeking someone to date their socially anxious son for a reward of a Buick Regal. Maddie, facing financial ruin, decides to take the plunge—understanding that "dating" comes with some unspoken complications.
When Maddie arrives at the Becker household, she meets Laird and Allison, who have a son named Percy. Percy, characterized by his extreme awkwardness and gaming lifestyle, seems less than the social butterfly his parents hoped for. Despite Maddie's age difference, she presents herself as the perfect candidate for the unconventional assignment. Striking an agreement, Maddie is instructed to keep their arrangement from Percy, which she reluctantly agrees to.
Thus begins Maddie's unique effort to win over Percy, starting with her visit to a dog shelter where Percy works. Dressed to impress, she begins to flirt but soon finds herself in a hilariously awkward situation when Percy reacts to her advances with discomfort, even resorting to spraying mace in self-defense. Their connection becomes an exploration of both their vulnerabilities as they embark on an unusual journey—stepping beyond comfort zones, sharing embarrassing stories, and establishing a bond that neither expected.
Their outings are filled with comedic moments, such as their skinny-dipping escapade interrupted by mischievous teens that lead to an adrenaline-fueled chase from the police. Maddie's unusual strategies to get Percy out of his shell often teeter on the edge of hilarity and emotional depth. A pivotal moment comes when Maddie reveals an embarrassing anecdote to Percy, showcasing the vulnerability that ties them together, even if initially for transactional reasons.
Soon however, the night with Percy reveals deeper feelings as they navigate their self-imposed roles and complicated lives. After unplanned encounters with familiar faces from their past, both characters wrestle with their feelings, leading to a comedic yet poignant dinner date that culminates in Percy embracing his true self, albeit with youthful exuberance.
Yet, as even brighter moments break through, the duo's journey isn't without its tumultuous twists. While attempting to fulfill the superficial expectations of their arrangement, Maddie’s fears regarding Percy’s attachment start to surface, ultimately leading to a confrontation that reveals the fragility of their transition from a mere agreement to genuine affections.
In the climactic moments, Percy's actions lead to a crash of unfortunate circumstance that directly impacts their budding relationship, exposing the raw emotions entangled in their complex agreement. As Maddie grapples with the repercussions of her choices, there’s an undeniable shift where the lines between love and obligation start to blur. Tension builds up until a frantic effort to reconcile reveals unexpected emotional truths, forcing both characters to confront their feelings and choices.
Amidst needles of humor and threads of reality, Maddie and Percy's last exchanges lead to an ever-evolving relationship. Will they conquer the peculiar challenges life has thrown their way? The film closes with a heartfelt tone as they decide on their futures, cementing the journey they undertook together—two seemingly different souls bound by laughter, chaos, and an unlikely friendship that teaches them both about growth, love, and the importance of facing one’s own vulnerabilities.
