The duo dated for nearly a decade before throwing in the towel in 2009. Since then, Jackson and Dupri have only been spotted together publicly once in 2017, as her “State of the World” tour came to an end in Atlanta.
However, with one of music’s biggest weekends this year, that all changed. The celebrated music icon brought in her 56th birthday early — her actual birthday is May 16 — with a surprise party in Las Vegas where she also attended both the Billboard Music Awards and the Lovers and Friends Festival.
When photos of the former couple snapped along with legendary music producer Jimmy Jam and Usher started circulating the web, it became inevitable that speculation of a rekindled romance and their past run at love would crop up among fans.
“He tryna sneak back in,” wrote one person, suggesting Dupri may be trying to woo Jackson.
“Jermaine got Janet out of London. She gonna have fun her birthday,” commented a second person.
A third wrote, ”Not Janet and Jermaine with the linkup after 13 years.”
Neither Jackson nor Dupri have given the speculation any public energy. The ”Control” singer has had her go at love play out in front of the world with her three failed marriages, but it is her relationship with Dupri that has most captivated fans. The former flames dated from 2002 to 2009; Dupri even helped produce Jackson’s ninth studio album, “20 Y.O.” The Atlanta producer shared in the past that he was on the receiving end of flak for the 2006 album’s lukewarm reception.
“I saw a lot of fans say, ’JD messed her career up with that album, ’” he told Page Six. ”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 added. Just as their musical chemistry proved to be not so hot, the couple called it quits three years later.
In recent years, Jackson has referred to her one-time-beau as a friend, though fans still could not wrap their heads around what could have led to their breakup. In January of this year, those curiosities were finally satisfied.
In Jackson’s two-night telecast of her revealing documentary, “Janet,” the producer admitted his infidelity led to the relationship’s demise. “One of the weird things is that dating Janet attracts other women — girls wanted to talk to me more because I was dating her,” said Dupri of how his ego and temptation got him caught up. In the documentary, Jackson echoed Dupri’s admission by revealing that rumors of her then lover creeping with other women had indeed gotten back to her.