A reserved, single English teacher comes out of her shell to help a former student realize his dreams of becoming a playwright in this warm-hearted comedy drama. Linda Sinclair (Julianne Moore
) teaches high-school English in Kingston, PA. Forty and single, she's content to spend her evenings curled up with a good book in her cozy apartment. Linda's staid routine is suddenly interrupted, however, with the unexpected reappearance of her most promising pupil, Jason Sherwood (Michael Angarano
). Having failed to make his mark as a playwright in New York City, Jason has returned home to Kingston humbled, and convinced that success has passed him by. Jason's domineering father Dr. Tom Sherwood (Greg Kinnear
) wants him to go to law school rather than wasting his time pursuing a career in the arts, and the rejected twentysomething is about to do just that when Linda makes the decision to mount his brooding play as a high-school production. With haughty drama teacher Carl Kapinas (Nathan Lane
) assuming the role of director, the Kingston High School stage is soon buzzing with activity. Meanwhile, as Linda embraces uncertainty for the very first time, she finds that in life as in romance, there are no rewards without risks.