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26. Janet Jackson and Wissam Al Mana
The singer married billionaire Wissam Al Mana from Qatar when she was 46 years old. Unfortunately the couple had called it quits just three months after they welcomed their first child together, after five years of marriage.

But before it unraveled, the two were very happy together. "I'm getting older and I feel more settled," she shared in an interview. "We have a deep bond, a deep connection."