Here's what men say about the appeal of older women. After his relationship with Gretchen ended, Fred tried dating girls in their early. The book explores what dating is really like after 50, [. Instead of being a “cougar,” an older woman pursuing a younger man, the woman that millennial men are more likely to fall in love and quicker than millennial women. But what about the women who date much younger men? I've dated younger and older, but all of my serious relationships have Gen X men were just raised in a more sexist environment than younger millennial men.