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In Martin Scorsese's adaptation of Edith Wharton's 1920 novel, romance between an upper-class gentleman and an ostracized lady is doomed by 19th century New York society. Shortly after his engagement to blandly genteel May Welland (Winona Ryder), Newland Archer (Daniel Day-Lewis) is reacquainted with May's scandalous cousin Ellen Olenska (Michelle Pfeiffer). As the head of an esteemed family, Archer initially uses his standing to try to rehabilitate Ellen's reputation, but he finds himself increasingly drawn to her disregard for the codes of New York manners. Bound by ingrained society mores and his peers' insinuations, Newland tries to dodge his growing passion by rushing his marriage to May, but he cannot keep himself from confessing his love to Ellen. Recognizing that Newland could never abandon his sense of honor and be happy, Ellen pushes Newland to May and leaves town. The marriage proceeds as dictated, but when Newland unexpectedly sees Ellen again, he yearns for the affair to come to fruition. However, he underestimates not only what May knows but also her ability to uphold the rules of propriety.

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