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Older Woman/Younger Man Relationships. Almost one-third of women between ages 40 and 69 are dating younger men (defined as 10 or more years younger). We often hear about older men dating women younger than they are, but in modern times, the pairing of older women with younger men makes sense. “Older successful men are used to being in control of a woman, and that doesn’t sit well with modern women,” says Susan Winter, co-author of the book “Older Women, Younger Men: New Options for