Linda Sinclair (Julianne Moore) is a high school English teacher in the small town of Kingston, Pennsylvania. She is passionate about her subject and popular with her students, but lives alone in simple circumstances. Cursed with a hopeless romantic soul, she lives in a world of men unable to match her impossible standards. When her former star pupil Jason Sherwood (Michael Angarano) returns from New York, crushed and insecure after failing to succeed as a playwright, Linda convinces him to produce his play at the school, as the play is far too good to never reach a stage. Jason’s overbearing father, Dr. Tom Sherwood (Greg Kinnear), pressures him to attend law school instead, which he finally relents to lest his ulcer be the end of him with no other prospects in sight. Complications arise after Linda and Jason, in a moment of impulsive creative madness, have a sexual encounter on her classroom desk. Various jealousies and rumours ensue, affecting her and everyone around her including the production of Jason’s play. When the school heads are confronted with proof of her indiscretion with a former student, Linda is fired on the spot. Embarrassed and in erratic egress from the situation, Linda storms off, gets into a minor car collision, and ends up at in hospital where she’s attended to by none other than Dr. Tom Sherwood. When she is moved by his gracious manner after having been mean to him on a previous occasion, she guiltily admits to having had sex with his son.
With surprise news of successful advance-ticket sales of beyond $18,000 for Jason’s atypical play, the headmaster is reluctant to miss out on the much-needed cash injection. He backtracks and persuades Linda to return and resume directing duties so the play may go on. However, there still remains another slight bone of contention. The school heads require a new ending for the play as they refuse to sanction the current one which they deem to be overly violent. They fear the parents will be outraged by its dark themes of murder and suicide. When Jason feels betrayed and refuses to rewrite the play’s ending, Linda is forced to come up with a suitable replacement herself, lest the entire play be a failure. After much soul searching, she manages to write an improved ending which Jason comes around to accepting when he realises the play will be a roaring success.
All is forgiven and Jason moves on to write further plays as Linda eases back into teaching and regaining her reputation. Sometime later, Linda runs into Jason’s father at her favourite bookshop. They catch up over coffee and both realise they’d totally misread each other previously. Grateful for all Linda has done for his son, and pleasantly surprised they have much more in common than previously thought, Tom, in spite of any remaining awkwardness, invites Linda on a further proper date. She, somewhat hesitantly, accepts the invitation.