Linda Sinclair (Julianne Moore) is a 40-year-old unmarried high school English teacher in the small town of Kingston, Pennsylvania. Her simple life turns an unexpected page when former student Jason Sherwood (Michael Angarano) returns home after trying to make it as a playwright in New York. On the verge of abandoning art and pressured by his father (Greg Kinnear), to face reality and go to law school, Linda decides to mount his play, a dark, angst-ridden, ambitious work as a Kingston High production, with flamboyant drama teacher Carl Kapinas (Nathan Lane) directing. Now well out of her comfort zone, Linda takes further risks in life and love, and the stage is set for a highly comic downfall. With the play, her reputation, and teaching career on the line, Linda finds an unlikely ally in herself. Amidst the ruins of her formerly perfect life, can she find a way to her own unique storybook ending?