Love is in the air, and fans say there is no time like the present for Janet Jackson and Jermaine Dupri to give love another try. The former couple has found themselves thrust into rumors of a rekindled romance again after being spotted hanging out in Atlanta.
Jackson was among the headliners of the One Music Festival on Oct. 29, where she reconnected with her old flame. The singer and megaproducer dated for about seven years beginning in 2002. In her “Janet Jackson” documentary on Lifetime, Dupri admitted that his unfaithfulness contributed to their breakup.
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Following the festival, a live stream showed Dupri and the pop star at his So So Def studio with Nelly and Ashanti, who recently began dating again after a 10-year hiatus, and several others.
An X user expressed that the video of the confirmed couple with Dupri and the “Together Again” singer had a certain “Spin the block double dates….” vibe.
“Everybody want that ol thang,” wrote another person, as a third suggested that “Janet is a businesswoman, that’s all it’s been. JD probably thought it was something more. She’s a hustler, and I’m not mad!”
The speculation of Dupri and his most notable ex circling back to each other has been an ongoing topic among fans whenever the two are spotted together.
Hopeful fans thought that his presence at Jackson’s 56th birthday bash last year was proof that they were indeed dating. He, however, would later debunk those claims.
Spin the block double dates….
— Luxap (@Luxuryaxp) October 30, 2023
The nostalgia of early 2000s romantic connections was enough for another fan to comment, “I was waiting on the camera to pan to Chilli & Usher.” TLC’s Chilli and R&B singer Usher dated for three years before breaking up for good in 2004.
In June, the TLC songstress revealed that she and the crooner were quietly off and on again in between relationships with other people post-split. Chilli claimed she cut off communication with him for good in 2019.
As fans may recall, Usher went on to marry his stylist, Tameka Foster, in 2007. They welcomed two sons, Usher V, and Naviyd Ely, before divorcing in 2009.
He would then secretly wed his manager, Grace Miguel, in 2015. They were together for two years as husband and wife when they announced their separation in March 2018. They divorced soon after. He is currently in a relationship with record executive Jennifer “Jenn” Goicoechea. They have two children: daughter Sovereign Bo and son Sire Castrello.
Like Usher, Jackson also found love again after her publicized breakup. She married Qatari businessman Wissam Al Mana in 2012.
The couple welcomed a son in 2017, but split three months after his birth. Their contentious divorce battle included a custody fight and claims that Mana ostracized her from her family.
Dupri has never married, but has two daughters from past relationships.
