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19. Janet Jackson
Janet Jackson has quite a tumultuous dating history that goes back to the first half of 1980s and that has included a few men younger than her, most notably Jermaine Dupri who was 6 years younger than Janet.
She finally settled down with a guy called Wissam Al Mana, an industrialist from the Middle East, 9 years her junior. Their relationship was kept almost completely out of the press and they even got married without much pomp.
Janet explained that she finds it easier to be with younger men because they are not so concerned who makes more in the relationship. She says her peers and older guys are all about ego and she doesn’t like it. We understand her completely and we wish her all the best.