The Truth About Janet Jackson And Jermaine Dupri's Complicated Relationship

Janet Jackson's personal life has always been of interest to the public. But aside from being a member of one of the most famous families in pop culture, she enjoys maintaining as much privacy as possible.

What most will know is that the "Miss You Much" hitmaker has been married three times. When just 18 years of age, Janet eloped with fellow singer James DeBarge, who was three years her senior, in 1984, per the Mirror. As noted in her BBC "Taking Control" documentary, Janet saw this marriage as a way of escaping her controlling father, Joe Jackson, who was her manager at the time. A year later, Joe had their marriage annulled after Janet found out DeBarge was battling drug addiction. In 1991, Janet gave marriage another shot by walking down the aisle with dancer, songwriter, and director René Elizondo at a private ceremony, according to E! News. After keeping everything hush-hush, they announced were getting a divorce in 2000. Janet's third and most recent marriage with billionaire businessman Wissam Al Mana began with another wedding away from the spotlight. The powerhouse entertainer didn't inform fans of their 2012 nuptials until the following year and noted on her website that it was "quiet, private," and a "beautiful ceremony." Shortly after welcoming their son, Eissa, in 2017, they called it quits.

Another flame that has been a big part of Janet's love life is her producer ex-boyfriend Jermaine Dupri. However, the relationship had its many ups and downs.

One year after the public found out about Janet Jackson's divorce from René Elizondo, she would end up meeting an unfamiliar face with whom she would spend many years of her life. While backstage at one of her concerts, Jermaine Dupri was introduced to Jackson. During an appearance on T.I.'s podcast, "expediTIously," he admitted he wasn't very well known at the time and was there as part of Kris Kross' entourage. Initially, Jackson's bodyguard wouldn't let Dupri in the room to meet the megastar. However, upon finding out that Dupri was standing outside the room, she vouched for him to be allowed.

Dupri felt Jackson had a certain "energy" about her, which resulted in him wanting to get to know her more. "So we became friends. I guess you wanna call it, I took my shot," Dupri recalled. Thanks to technology and Jackson's stylist, the pair were able to connect after that meeting. When he learned Jackson didn't own a two-way pager, Dupri took action. "I got the address from her stylist, and I sent her the two-way," he said, adding, "I'm thinking like, I'm gonna get the number, and you gon' hit me back. ... She hit me back! It was like, at that point, let's hang out, let's kick it."

Janet Jackson sings about being "well-traveled" on the 2015 song of the same name. However, there was so much of the world she had yet to be exposed to when she began dating Jermaine Dupri. While Jackson was spending time with the hit-making producer, he allowed her to enjoy life outside what T.I. described as "the bubble of the Jacksons" on his "expediTIously" podcast.

"I took her to Magic City. ... I exposed her to a lot of life that I didn't even know I could expose a person to," Dupri stated, adding, "You think when somebody's that famous, that rich, they know everything. They've seen everything. But it was a lot of world that we was living in here ... cultural-wise, that they hadn't gotten in L.A. That's where we basically started hitting it off. We were showing each other multiple things. ... It was two cool people exchanging energy."

While Jackson was doing a sit-down interview for "The Oprah Winfrey Show" in 2006, Dupri sat in the audience. Host Oprah Winfrey shared a quote previously said by Jackson that read, "Jermaine has taken me places I haven't been before." When Winfrey asked her to elaborate on what she meant, Jackson jokingly stated they'd been to Egypt before laughing with the audience. She then got serious, expressing that she "thank[s] God on a regular basis for" having Dupri in her life.

During a 2006 appearance on "The Tyra Banks Show," Janet Jackson delved into her sex life with Jermaine Dupri and made quite the statement by telling viewers that he is "off the charts" in bed. When host Tyra Banks asked the Grammy Award winner whether having sex in your 40s is better than in your 20s, Jackson replied with "hell yeah," adding, "you can't compare." Even though Jackson politely asked Banks to stop asking questions about her sex life, Jackson would continue to brag about how great Dupri is, explaining that he "doesn't hurt." She even revealed that she had faked an orgasm on all her albums minus the one she was promoting at the time, which featured Dupri as a producer on many of the songs.

That same year, Jackson told Essence magazine that she felt like she "finally met my match" in Dupri as he also has a high sex drive (via PopDirt). "In relationships it was always the guy telling me, 'OK, hold on, wait a minute.' I'd ask my girlfriends, 'Aren't we supposed to be the ones who say, 'Wait, not tonight, I have a headache?'," she said. "But with Jermaine, I don't have to say anything; he knows I'm ready. Any time, any place." This includes during a commercial flight, Jackson told Tyra.

Over the years, Janet Jackson has been open about her weight fluctuating up and down, admitting that she emotionally eats. In 2012, she told Prevention that she gained so much weight in 2005 that she was in danger of developing diabetes. "Even when I lost it [and] then gained quite a bit back, there was always the thought of heart disease," she said, adding, "I honestly don't even know what size I am. Now it's about looking in the mirror and saying, I feel good. I feel healthy."

While on "The Oprah Winfrey Show" in 2006, Jackson was joined by Jermaine Dupri on the couch halfway through her interview. The "Love Will Never Do (Without You)" hitmaker told host Oprah Winfrey that Dupri accepted her at any size and it was him who helped the singer learn to love herself no matter what. "I've never been with someone who just looks into my eyes and grabs all my stuff," she explained before bursting into laughter. "He would grab my extra little meat that I had, and he would look into my eyes and say, 'I love you and this needs love too.'"

In 2006, Janet Jackson released her ninth studio album, "20 Y.O." In addition to working with longtime producers Jimmy Jam and Terry Lewis, she decided to take her relationship with Jermaine Dupri to the next step by allowing him to produce on a number of the tracks. On the US Billboard 200, the LP peaked at No. 2 and spawned three singles — "Call On Me" with rapper Nelly, "So Excited," and "With U." As noted by the RIAA, "20 Y.O." went platinum, selling more than 1 million copies worldwide. Along with being a mini success on the charts, "20 Y.O." was honored with a Grammy Award nomination at the 49th annual ceremony for Best Contemporary R&B Album.

Prior to this album, Dupri had remixed Jackson's 2001 single "Someone To Call My Lover." And it wasn't the only other time they worked together – one year before the record dropped, Jackson appeared in Dupri's music video for his single "Gotta Getcha."

After many happy years together, Janet Jackson and Jermaine Dupri's relationship started to take a hit when Dupri wasn't willing to take their romance to the next level. While discussing their relationship with rapper T.I. on his "expediTIously" podcast, Dupri admitted he realized marriage with the legendary performer wasn't for him. "I started seeing so many other things that I wanted to do, and so many other places that I felt like I wanted to go. I started thinking marriage for me wasn't gonna work," he explained, adding. "Just something about it. When you feel like you're ready to get married, you don't really have no answers, you just know when it is."

Even though Jackson and Dupri never walked down the aisle and exchanged vows, he revealed he already felt married to the star. While being interviewed on "The Tyra Banks Show" in 2008, Jackson squashed the rumors that suggested they were planning a wedding. The "Just A Little While" hitmaker informed viewers and the talk show's host, supermodel Tyra Banks, that she had never stepped into a bridal shop before and stated that if the two were to ever marry, Dupri would want the whole world to know about it.

Jermaine Dupri not wanting to marry Janet Jackson was just one factor as to why their relationship started to fall apart. Another reason was that the pair never lived together throughout the long period they were involved romantically. "I feel like ... that's where you really determine if you're strong," Dupri explained to T.I. on his "expediTIously" podcast.

Along with that, Jackson didn't want to move to Atlanta, where Dupri was living at the time. "She was willing to come out here for a couple of weeks. But living in Atlanta, for her, just didn't really seem like L.A.," he said. In addition to that, Dupri also wasn't committed enough to move to where Jackson was staying either. "I wasn't ready to move to Malibu ... I like it, I f**k with it. But it ain't ... It's just something about being here. ... That stuff didn't feel like the space where either one of us wanted to be," he continued. Because of this, their bond wasn't as strong as it seemed to the public, leading them to ultimately call it a day in 2009 after falling in love in the early 2000s.

In 2006, Janet Jackson teamed up with rapper Khia, who is predominantly known for the song "My Neck, My Back," for the single "So Excited." The track was produced by Jackson's boyfriend at the time, Jermaine Dupri, who also featured in the music video. During an online live stream, Khia claimed that Jackson cut her out of the majority of the video because Jackson thought she was hooking up with Dupri behind her back. As of this writing, this has never been confirmed.

During the making of the video, Jackson and Khia were never seen on set together at the same time. When Khia was asked how she managed to bag herself a feature with Jackson, she explained it was all down to Dupri while stating the collab was the "perfect match." Even though Khia didn't have nice words to say about Jackson on her live stream, she described the pop icon as "so down to earth and so real" on the day of the video shoot.

After Janet Jackson split from her third husband, Wissam Al Mana, in 2017, rumors suggested that she was getting back with Jermaine Dupri nearly a decade after their breakup. As reported by Bossip, an inside source claimed that "things have been heating back up between the former couple, who have recently reunited and not just for music making purposes." After the internet went wild, Dupri put the headlines to rest.

"All of this is just speculation, I guess, when somebody gets single. The fans actually really want to see us back together, so people actually [have] been championing this, but none of this is actually true," he said on "The Breakfast Club" in January 2018, adding, "I dated Janet for d**n near 10 years. I don't have to hide. ... Why I'm gonna sneak around with somebody that y'all know I been with? ... I know her better than the dude she married."

In addition to that, rapper Bow Wow shared a throwback snapshot of Dupri and Jackson in a now-deleted Instagram post in 2021. In the caption, he suggested they should get back together and that Dupri likely misses Jackson, per That Grape Juice. However, it seems they are just on friendly terms. Later that same year, Jackson wished Dupri well on his birthday in a tweet.

Janet Jackson's 2006 album "20 Y.O." may have scored her a Grammy Award nomination, but it wasn't a hit in the eyes of a number of critics. On Metacritic, the LP has a Metascore of 52 out of 100, receiving mainly mixed or average reviews. The album managed to sell over 1 million copies, but this was a lot fewer than many of Jackson's previous releases, per ChartMasters. Unlike the majority of her albums, she didn't promote the record with a tour either.

In 2020, Jermaine Dupri, who served as a producer on the album, explained to Page Six that future music between him and Jackson is very unlikely. "The only reason I say that is because I feel cheated in a way from the '20 Y.O.' album that I did ... a lot of people discredit me for that album. It has nothing to do with me and her," he said. Not only that, Dupri claims fans unfairly blame him for the lukewarm reception "20 Y.O" got in comparison to her past records. "I saw a lot of fans say, 'JD messed her career up with that album' . . . That album almost sold 400,000 copies in its first week and produced a No. 1 hit. I don't know why that's not a success," he continued.

For many years, we were led to believe the main reason for Janet Jackson and Jermain Dupri's split was due to them not wanting to get married and their decision to live far apart from one another. However, in Jackson's two-part documentary, "JANET," which debuted on A&E and Lifetime in January 2022, more was revealed to the story.

Dupri, who featured in Jackson's doc, confessed he was "reckless" during their seven-year relationship, per The Source. "One of the weird things about dating Janet is that dating Janet attracts other women," the head of the So So Def record label said, adding, "Girls wanted to talk to me more because I was dating her, which was really weird." Dupri ultimately admitted to being unfaithful to the singer, resulting in fans being mad. Jackson insisted that Dupri was "constantly working" and that there were times when she wasn't getting "enough from him emotionally."

Even with all this being out in the open, Jackson and Dupri have managed to remain friends, despite their many differences over the years.