Janet Jackson
Singer and songwriter Janet Jackson had an interesting life, and her relationships are only a small part of it. She was married four times, the first time at the age of eighteen. Naturally, this marriage was over within a year (because you can’t really know what you want at this age, right?). Her second marriage came six years later, and this time it lasted nine years and officially ended in 2000. Perhaps the reason why this marriage was a relative success is because it was kept a secret! Jackson’s second marriage was only revealed when the couple had announced their separation.

In 2012, Jackson married Qatari businessman Wissam Al Mana, once again in a private ceremony, after two years of dating. In 2017, the couple welcomed to the world their first (and only) son, Eissa Al Mana. Shortly after his birth, the couple announced their separation. Since then, details about Jackson’s dating life have been vague, but in 2019, she shared that she was a single mother, struggling with raising her son alone and maintaining her busy career. Despite the struggles, Jackson said, she was enjoying every minute of it.