Oliver Barrett IV is a student at Harvard College, where he won a hockey scholarship. His family are wealthy, socially well-connected and fully expecting Oliver to marry a young woman of similar standing. When Oliver meets Jenny Cavilleri, all of his own expectations go out of the window. Jenny is a beautiful, intelligent and quick-witted classical music major at nearby Radcliffe College. Jenny is a working-class girl and the two would seem to have nothing at all in common, but surprisingly they see past their own differences, and fall in love.
Jenny has made many plans for herself, plans that she made before meeting Oliver, and plans that she fully intends to follow through. When she tells him that she is going to move to Paris to continue her studies, Oliver is very upset because the plan does not include him. He proposes to Jenny; when she accepts, he takes her home to the Barrett family mansion so that he can introduce her to his parents. The meeting does not go well. The Barretts are not in favor of the relationship and Oliver's father later tells him that if he marries Jenny then he will be disinherited. Oliver loves Jenny and so marries her anyway.
Oliver has never had to live without his family's financial support and so the early days of their marriage are rather difficult. Jenny finds work as a teacher so that Oliver can attend Harvard Law School, and after graduating third in his class he takes a position with one of the most prestigious law firms in New York. Things begin to look up. They also want to start a family, but this seems to be more of a struggle than they had anticipated. Jenny's doctor runs some tests to see why she is having such difficulty getting pregnant; the tests reveal that she is suffering from terminal cancer.
Oliver tries to keep Jenny's illness a secret from her and goes through the motions of their life behind a facade of normality, but Jenny demands that her doctor tells her the truth. Oliver goes to his father for help; they have not spoken since the wedding, but he needs financial assistance to pay for Jenny's cancer treatment. His father assumes he has got a girl in trouble and gives him money without enquiring any further what it might be for.
Jenny and her father make her funeral arrangements together as she lays in hospital. When Oliver arrives, she tells him that she is glad that she chose being with him over pursuing her musical career; he never held her back, and it was not a sacrifice because it meant that they could be together. Oliver holds her tightly as she dies in his arms. Oliver is overcome with grief. He meets his father outside the hospital; he has learned about Jenny's illness and wants to help. When Oliver tells him that Jenny is dead, his father tells him that he is sorry, to which Oliver replies, "Love is never having to say you're sorry." He walks over to the ice rink where Jenny had watched him skate the day she was taken into the hospital.
