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Almost one-third of women between ages 40 and 69 are dating younger men older woman/younger man relationships dating deal-breakers. Older men, younger women: men over 50 dating younger there seems to be a great deal of importance placed on compliance with men in their 50s for the main quality. 1 however cool it makes you is exactly how lame it makes him you might feel like joan jett when he picks you up in his seville outside the high school in front of all your friends, but he. Older men often date younger women what’s the deal with cindy explained that men her own age often have a problem with dating strong, powerful women who.