Maddie is an Uber driver and bartender in a small seaside town, struggling to make ends meet as she faces the loss of her childhood home. Desperate for cash, she answers an unusual Craigslist ad placed by two wealthy helicopter parents, Laird and Allison. They are seeking someone to "date" their awkward and introverted 19-year-old son, Percy, before he heads off to college. The task is simple: help boost his confidence and ensure he gains some social skills. Maddie agrees, seeing it as a straightforward way to earn the money she desperately needs. As Maddie tries to break Percy out of his shell with a variety of well-intentioned yet humorous schemes, she discovers that he is far more complex and sensitive than she anticipated.

However, as she embarks on this unconventional mission, Maddie begins to confront her own life choices, questioning her motivations and the ethics of her agreement. Despite Percy's initial hesitance, their interactions lead to unexpected growth and understanding for both of them. Challenges arise that test Maddie's resolve and force Percy to face some of his own fears. As events unfold in surprising ways, the experience for both Maddie and Percy becomes more about self-discovery and genuine connection than fulfilling a transaction. The story delves into themes of friendship, personal growth, and the complexities of the transition into adulthood.