A precocious and disarmingly articulate 15-year-old, Oscar Grubman, returns home to Manhattan for Thanksgiving break from his elite boarding school. Far more interested in the complexities of French philosophy and the allure of mature women than the antics of his peers, Oscar finds himself hopelessly smitten with his stepmother, Eve. His idealistic pursuit of her heart, however, leads him into a complicated and unexpected romantic entanglement with her best friend, Diane, a sophisticated and alluring woman closer to his father's age. As Oscar navigates the treacherous waters of adult desire and intellectual pretension, his naive worldview collides with the messy realities of the grown-up world he so desperately wants to join. This witty and tender coming-of-age dramedy, featuring a breakout performance from Aaron Stanford alongside Sigourney Weaver and Bebe Neuwirth, captures the awkward, poignant, and often humorous chasm between youthful idealism and lived experience.