19. Janet Jackson
After many failed relationships, Janet Jackson finally settled down with Wissam Al Mana, a rich industrialist from the Middle East who is 9 years younger than the pop superstar. The two kept their relationship low key and tied the knot under the radar. And the age gap? Jackson doesn’t have a problem with being married to a younger man; in fact, she couldn’t be happier to be with someone younger.
The singer was previously linked to producer Jermaine Dupri, 6 years her junior. The pair went steady for seven years before calling it quits, but Janet didn’t hide her opinion about dating a younger partner even then.
In a nutshell, here’s what the hitmaker said about relationships in which the woman is older:
“I came to realize that younger men had less of a problem with who I am than older men. With the younger guys, there was less ego. Things were less competitive. They weren’t threatened by who made more and who made less.”