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Janet Jackson was recently spotted attending the 1500th performance of Cabaret’s West End revival at the Kit Kat Club in London.
The All for You singer-songwriter was dressed in an all-white suit. During her appearance at the Cabaret at the Kit Kat Club performance, a specific video of Jackson’s also garnered the attention of many X users.
Janet was seen holding Maxwell’s hand as they arrived together at London’s Playhouse Theatre. The short clip almost immediately sparked dating rumors on X, with many shipping the pair.
Neither Janet Jackson nor Maxwell has responded to the speculations around their relationship. For those unaware, the Unbreakable singer has kept her dating life private since her divorce from ex-husband, Wissam Al Mana.
Read on to learn more about the “Why Did I Get Married?” star’s relationship history.
A look at Janet Jackson’s dating history
The Poetic Justice actor’s first-ever publicly known relationship was with James DeBarge, whom she started dating at 16. The pair eloped in 1984 to get married, without the knowledge of Janet Jackson’s parents. The singer-songwriter reflected on her relationship and decision to marry DeBarge at a young age, in her namesake 2022 Lifetime documentary (via the New York Post),
“I wanted to be able to stand on my own feet. [...] And at that time I thought that there was no other way I would be able to kind of get my own life — unless I got married.”
Per her two-part documentary, James DeBarge had a drug problem, and Janet “would go searching the streets looking for him.” She also revealed that her then-husband left her alone on their wedding night. Eventually, the marriage got annulled in 1985, and Janet Jackson was next linked with René Elizondo Jr., a Mexican dancer, songwriter, and music video director.
The former couple met during the 1980s, but did not start dating immediately. At the time, Elizondo was a backup dancer for Janet’s sister La Toya Jackson. The Dream Street singer started as a friend of her future husband, whom she married in 1991. Janet Jackson recalled during the 1993 issue of EBONY (via Closer Weekly),
“When I first met him, I was going through so much, and I would call him and I would cry on the phone. And he was going through some stuff too with his girlfriend. We were best friends.”
They reportedly split in 1999 and got divorced in 2000. During the late ‘90s, Janet Jackson was linked with rapper Q-Tip, with whom she had worked on Poetic Justice (1993). They collaborated again for the song Got ‘til It’s Gone. In 2021, Q-Tip revealed during a chat with Math Hoffa that he and Janet Jackson briefly dated after their late ‘90s collaboration. He said (via 107.5 FM WBLS),
“We started dating after that,” Q-Tip said. “It be cool and s***. She be making eggs and s*** and I’ll be chilling like, ‘Yo, that’s Penny! to myself. I love her to death and it’s like she’s a Jackson. That’s Black royalty.”
After her divorce from René Elizondo Jr., Janet also went out with Matthew McConaughey. The How to Lose a Guy in 10 Days star admitted on Watch What Happens Live With Andy Cohen in 2019 (via SheKnows),
“We went out and had dinner one night and had dinner. That was sort of it.”
According to Close Weekly, Jermaine Dupri and Janet Jackson dated between 2002 and 2008. The rapper reportedly attended one of Jackson’s shows and met her backstage. Despite going out for six years, the pair parted ways because Dupri didn’t want to marry, while neither wanted to relocate for the other. Jermaine once recalled on his podcast,
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“I started seeing so many other things that I wanted to do, and so many other places that I wanted to go. I started thinking marriage for me wasn’t gonna work. Just something about it. When you feel like you’re ready to get married, you don’t have no answers, you just know what it is.”
Janet started dating a Qatari businessman, Wissam Al Mana, in 2010, whom she met in Dubai in 2006. They tied the knot in 2012 and welcomed their only son, Eissa, in 2017. The reports of the split also started emerging the same year, which Janet Jackson confirmed later.
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