#28: Madonna and Guy Ritchie

Why is it that when older women date younger men, so many people have something to say about it? Men in Hollywood are given so many more chances to screw up than women, and dating is no exception… But if you’re an older woman who happens to look phenomenal and fancies younger guys, we say go for it.

The queen of pop herself, Madonna has been known to date guys much younger than herself. And was even married to Guy Ritchie from 2000 to 2008, who is 10 years younger than her. Since her divorce from Guy, she has had no issue dating some guys that are much younger than her.