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Breakup to Makeup: 38 On-Again, Off-Again Celebrity Couples
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Janet Jackson and Jermaine Dupri

  • 2002: Janet and Jermaine first began dating.
  • 2009: After working together on music and seven years of dating, the couple broke up. While the reason for their split remains unknown, it appeared the pair ended things on good terms. "Jermaine is one of my best friends," Janet said in a radio interview shortly after their split. "I love him to death. We're still connected. We're still good friends. We still talk."
  • 2012: Janet quietly tied the knot with Qatari billionaire Wissam Al Mana.
  • 2017: Janet welcomed her first child, a baby boy named Eissa, with Wissam in January, and three months later, she and Wissam split. Jermaine reportedly reached out to Janet after her separation, and in December, reports surfaced that the couple had decided to give their relationship another shot. Janet and Jermaine have yet to confirm anything, but the music mogul did accompany Janet to her State of the Union World tour afterparty that same month and the two were reportedly seen "cuddled up and holding hands."
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