Top 100 Older Woman Younger Man Relationship movies
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The First Time (1969)
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With the coming of summer, three high school buddies--Kenny Leeds, Mike Decker, and Tommy Kingsley--anticipate their initiation into the pleasures of manhood. But Kenny is separated from his friends and sent to stay with his grandparents in Buffalo while his father, a widowed salesman, leaves on a business trip with his secretary-fiancée. Bored and alone in a strange city, Kenny writes his two friends letters about his adventures at "Rosie's," a fictitious brothel across the Canadian border in Niagara Falls. His lie quickly backfires.
The Graduate (1967)
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Benjamin, a recent college graduate very worried about his future, finds himself in a love triangle with an older woman and her daughter.
Goodbye Again (1961)
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Middle-aged businesswoman Paula Tessier rejects the advances of her client's amusing 25-year-old son, Philip Van der Besh, but reconsiders when her longtime philandering partner begins yet another casual affair with a younger woman. She soon learns that May-December romances with older women are frowned upon in society.
A Cold Wind in August (1961)
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An older woman gets involved with her young neighbor.
The Roman Spring of Mrs. Stone (1961)
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Critics and the public say Karen Stone is too old -- as she approaches 50 -- for her role in a play she is about to take to Broadway. Her businessman husband, 20 years her senior, has been the angel for the play and gives her a way out: They are off to a holiday in Rome for his health. He suffers a fatal heart attack on the plane. Mrs. Stone stays in Rome. She leases a magnificent apartment with a view of the seven hills from the terrace. Then the contessa comes calling to introduce a young man named Paolo to her. The contessa knows many presentable young men and lonely American widows.
Breakfast at Tiffany's (1961)
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Holly Golightly is an eccentric New York City playgirl determined to marry a Brazilian millionaire. But when young writer Paul Varjak moves into her apartment building, her past threatens to get in their way.
Crazed Fruit (1956)
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Two brothers compete for the amorous favors of a young woman during a seaside summer of gambling, boating, and drinking.
Tea and Sympathy (1956)
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A sensitive young man recalls his time in boarding school when the only person who seemed compassionate towards with him was his housemaster's wife.
All That Heaven Allows (1955)
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Two different social classes collide when Cary Scott, a wealthy upper-class widow, falls in love with her much younger and down-to-earth gardener, prompting disapproval and criticism from her children and country club friends.
Another Man's Poison (1951)
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Mystery novelist Janet Frobisher, lives in an isolated house, having been separated for years from her criminal husband. She has fallen in love with her secretary's fiancé and when her estranged husband unexpectedly returns, Janet poisons him, but just as she's about to dispose of the body, one of her husband's criminal cohorts also shows up.
The Young and the Damned (1950)
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A group of juvenile delinquents live a violent life in the infamous slums of Mexico City; among them Pedro, whose morality is gradually corrupted and destroyed by the others.
Dodsworth (1936)
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A retired auto manufacturer and his wife take a long-planned European vacation only to find that they want very different things from life.