Jesse Fisher, a 35-year-old college admissions officer in New York City, is invited back to his alma mater in Ohio to attend the retirement dinner of his favorite professor. During his visit, he meets 19-year-old Zibby, a current student with whom he forms an immediate, deep connection. Zibby introduces Jesse to a renewed sense of possibility and love for the arts, urging him to embrace his passion for literature and music, which he had set aside in his mundane adult life. The interactions rekindle his enthusiasm for liberal arts and spark an introspective journey about where his life is headed.

As Jesse grapples with their age difference and his own existential concerns, he encounters a series of other characters who each impact his outlook in subtle ways. These include Dean, a free-spirited student grappling with his place in the world, and Professors Judith and Peter Hoberg, who offer contrasting views on life's complexities. Jesse is faced with emotional and ethical dilemmas that challenge his preconceived notions about life, love, and personal growth. Through these relationships, Jesse begins to reassess his choices and what he truly wants out of life, leading him to a profound realization about his past and future.