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"Where does a woman's sympathy leave off -- and her indiscretion begin?"
Seventeen-year-old Tom Robinson Lee, a new senior at a boy's prep school, finds himself at odds with the machismo culture of his class in which the other boys love sports, roughhouse, fantasize about girls, and worship their coach, Bill Reynolds. Tom prefers classical music, reads Candide, goes to the theater, and generally seems to be more at ease in the company of women.
The other boys torment Tom for his "unmanly" qualities and call him "sister boy," and he is treated unfeelingly by his father, Herb Lee, who believes a man should be manly and that his son should fit in with the other boys. Only Al, his roommate, treats Tom with any decency, perceiving that being different is not the same as being unmasculine. This growing tension is observed by Laura Reynolds, wife of the coach. The Reynolds are also Tom's and Al's house master and mistress. She tries to build a connection with the young man, often inviting him alone to tea, and eventually falls in love with him, in part because of his many similarities to her first husband John, who was killed in World War II.
The situation escalates when Tom is goaded into visiting the local prostitute to dispel suspicions about his sexuality, but things go badly. His failure to lose his virginity causes him to attempt suicide in the woman's kitchen. His father arrives from the city to meet with the dean about Tom's impending expulsion, having been alerted to Tom's raffish intentions by a classmate. Assuming his son's success, he gets one of the film's biggest send-ups as he boasts of his son's sexual triumph and time-honored leap into manhood until the Reynolds inform him otherwise. Laura goes in search of Tom and finds him where he often goes to ruminate, near the golf course's sixth tee. She tries to comfort him, counseling that he'll have a wife and family some day, but he's inconsolable. She starts to leave, then returns, takes his hand, and utters the film's famous line, "Years from now when you talk about this, and you will, be kind."
The film opens and closes ten years into the future, when the adult Tom, who is now a successful writer and married, returns to his prep school. The final scene, new to the Hollywood version, shows Tom visiting his old coach and house master to ask after Laura. Bill tells him that, last he's heard, she's out west somewhere but he has a note from her to him, which she enclosed in her last letter to her ex-husband. Tom opens it outside and learns she wrote it after reading his published novel derived from his time at the school and their relationship. After their moment of passion, she tells him, she had no choice but to leave her husband.