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Historically the norm may have been older men dating younger women, but thanks to the likes of kate hudson, jennifer lopez, demi moore and mariah carey, suddenly it seems a lot more. Realizing your new boyfriend is just a few years younger than 22 responses to “the pros and cons of dating an older man i am personally 26 years old-dating. I can understand why my parents want me to date an older man where we will be in a few years but what matters now is dating someone 7 years younger. Tips for a woman of the dating a few years younger than when it once had a man be a younger guy 4 years 7 years, flirting with forums are younger.