Despite her status as a global superstar, Janet Jackson is known to keep her private life fairly discreet. This is especially true of the last decade or so, as she has continued to shy away from the limelight, save for a few high-profile outings. Recently, however, Jackson made waves across social media by appearing arm-in-arm with R&B singer Maxwell during a “Cabaret” performance. As fans continue to dig into the pair’s business, one question keeps popping up: are they dating?
Though there’s not much to go on, it certainly seems like the duo is more than just friends, so it’s worth investigating the life, relationships and dating history of Janet Jackson, just to see what we can learn. Whether you’re an old school fan dating back to her earliest records, or a relatively new listener enamored with the possible tea of an emerging R&B power couple, be sure to read ahead.
Who Was Janet Jackson’s First Love?
Since Janet Jackson has been a fixture in popular culture since the late 1970s, her romantic interests have been scrutinized for several decades. The prolific performer has had several marriages, a few notable flings and a variety of high-profile romances documented by tabloids and social media posts.
Jackson’s earliest known relationship, as far as the public is aware, kicked off in 1982, when she was just 16 years of age. At the time, she was dating fellow singer-songwriter James DeBarge. The couple quickly attracted the attention of tabloids and the listening public, and even eloped after seeing each other for two years. After just a year of marriage, however, the power couple had their union annulled. According to Janet Jackson herself, the relationship deteriorated as DeBarge became heavily addicted to drugs.
One bizarre detail regarding Janet Jackson and James DeBarge’s now decades-old love story is the long-standing rumor that the couple has a child together. DeBarge claimed for years that Jackson had carried his child in secret, though she repeatedly refuted these claims. Most recently, she addressed the rumors in an episode of her self-titled A&E reality series, stating, “Back in the day they were saying that I had a child and I kept it secret. I could never keep a child away from James. How could I keep a child from their father? I could never do that, that’s not right.”
She went on to explain the reasoning behind the fan speculation, arguing, “A lot of the kids thought I was pregnant because I had gained weight. I had started taking birth control pills, and back then, you could pick up weight taking them. And that’s what happened to me. So that rumor started going around.”
Did the ‘Poetic Justice’ Actress Date Tupac?
Though Janet Jackson and the late rap icon Tupac Shakur sparked many dating rumors over the years, the two never officially embarked upon a romance. According to frequent Tupac collaborator Spice 1 however, that wasn’t for lack of trying on part of the “California Love” vocalist.
Apparently, Pac had attempted to court Janet during the early 1990s, especially when they worked alongside each other filming the 1993 movie “Poetic Justice.” As Spice tells it, Janet Jackson was considering Pac’s offer, but ultimately turned him down after learning that he had hooked up with one of her dancers. Having heard tales of Tupac’s promiscuous nature, she also allegedly demanded that the rapper take an AIDS test before agreeing to go on a date with him. However, this request offended him, leaving the pair to remain platonic.
Why Did Janet and Jermaine Dupri Break Up?
Janet Jackson and record producer Jermaine Dupri served as one of music’s greatest power couples from 2002 through 2009. As Dupri has noted on more than one occasion, their relationship lasted longer than most celebrity marriages. In fact, the couple had even become engaged at one point, and had spoken about settling down and having children before their relationship deteriorated. Janet and Jermaine addressed the highs and lows of their relationship during an episode of the “Janet Jackson” docuseries, with Dupri clarifying, “Dating Janet attracts other women. Girls wanted to talk to me more because I was dating her.”
The producer admits that he became unfaithful due largely to the major press he received from the relationship, as Janet herself noted, “I needed more than what he was giving me. He was a workaholic, and he was constantly working. I would not see him for like three weeks, a month.” Though the duo still clearly have much love for one another today, their relationship officially became untenable in 2009, forcing them to go their separate ways before Jackson ultimately struck up a romance with Qatari businessman Wissam Al Mana in 2010.
Did Janet Jackson Marry a Billionaire?
You might not think it’s possible for Janet Jackson to marry up financially, thanks to her massive net worth, though that’s exactly what happened when she settled down with Wissam Al Mana. Al Mana was a prolific businessman overseeing a variety of businesses all over the globe, accounting for an estimated net worth of over $1 billion, according to Celebrity Net Worth. The pair secretly wed in 2012 and only announced that they were officially married in 2016, when Janet postponed several tour dates to accommodate some family planning.
By January of 2017, Janet Jackson had given birth to her first and only child, Eissa Al Mana. Shortly thereafter, the couple split up, sparking rumors about the fragility of their relationship. Some sources across the web have suggested that Jackson received a $100 million payout for providing Al Mana with a male heir, as per a prenuptial agreement, though both of the wealthy parents have refused to speak on the situation publicly.
Either way, Janet Jackson has been very public with her motherhood journey, describing the process of raising Eissa as the “Most important thing I’ve done, the biggest thing I’ve done.” Per a write-up in People, Jackson has articulated, “Obviously, you have to work, but you don’t come first anymore. Your life completely changes. And I wouldn’t trade it for anything.” It has also been rumored that Jackson’s pregnancy was made possible via a donor egg, due to her age. According to a 2016 report in Stat News, obstetrician-gynecologist and fertility researcher David Keefe has speculated, “It’s exceptionally rare for patients to get pregnant naturally at 50 or over 45. They make history.”
What We Know About the Maxwell Dating Rumors
Like many of Janet Jackson’s exploits, we don’t have direct confirmation that she’s dating Maxwell at this time. Still, it would be a bit surprising to learn that they’re just friends, especially after they were spotted holding hands at the “Cabaret” show. Their outfits at the event even go together perfectly, suggesting they were likely styled with the other party in mind, and arrived together. Could this be another serious celebrity romance for one of music’s biggest legacy acts or another short-lived fling? For now, we’ll have to stay carefully tuned to Janet’s next public moves to know for sure.
Frequently Asked Questions
How many marriages has Janet Jackson had?
Janet Jackson has been married three times. All three relationships have involved private ceremonies, and the public was left in the dark until after the marriage became official. Janet’s husbands include singer James DeBarge, dancer René Elizondo Jr. and Qatari billionaire Wissam Al Mana.
How much money did Janet get from her divorce?
Janet Jackson is said to have received a payout of $200 million in the wake of her divorce from Wissam Al Mana. This figure represents two separate clauses in the couple’s prenuptial agreement. One portion of the agreement apparently stated that Janet would receive $100 million if the marriage lasted over five years. At the same time, the other suggested she’d be paid another $100 million after birthing a male heir for Al Mana. In 2017, she accomplished both feats just before the marriage officially ended.