Bow Wow is hoping for a romantic reunion between Jermaine Dupri and Janet Jackson.
During a recent appearance on Club Shay Shay, the rapper shared his candid thoughts on their past relationship, revealing he still holds out hope for them to rekindle the spark. Dupri and Jackson dated for seven years, from 2002 to 2009. Their bond wasn’t just romantic—it was creative. Dupri co-produced Jackson’s albums 20 Y.O. and Discipline, contributing to some of her most personal work.
Around the 1:42:00 mark of the interview, Bow Wow told host Shannon Sharpe that Ashanti and Nelly’s reconciliation was one of the most iconic “spin the block” moments in pop culture. When asked if he’d like to see Dupri and Jackson follow suit, he responded without hesitation: “I do want that to happen.”
He spoke fondly of Jackson, describing her as “the sweetest, coolest person ever.” For Bow Wow, she wasn’t just a superstar—she felt like family. “It’s like the best stepmom you could have,” he said, reminiscing about simpler moments like seeing Jackson do the dishes or drive out to grab tacos without any fuss. “Ms. Janet, man, was everything.”
He went on to explain that their breakup left a mark on those close to the couple. “You know it’s real when they split and you’re mad at your boy,” Bow Wow said. “That’s how we all felt about JD. We were like, ‘Man, please fix it. Get her back.’”
He praised the connection Dupri shared with the pop icon, saying the producer was “at peace” when they were together. Jackson, he added, is a “beautiful person” who brought a calming energy to those around her.
Janet Jackson moved on and later married Qatari billionaire Wissam Al Mana in 2012. The couple had a son and divorced in 2017. Meanwhile, Dupri made a rare public appearance in Jackson’s 2022 Lifetime documentary.
He acknowledged that while he once proposed to Jackson, their relationship fell apart because of his own behavior. Jackson reportedly heard rumors of infidelity, which Dupri didn’t deny. “Girls wanted to talk to me more because I was dating her, which was weird,” he admitted in the film. “And I was a man.”
In June 2023, Dupri reflected on the lost relationship in a tweet that suggested lingering regret, writing that he “fumbled” Jackson.
While time has passed and both artists have lived full lives since, Bow Wow’s nostalgia reflects a sentiment many fans share. For those who watched their love story unfold in the 2000s, the idea of Dupri and Jackson finding their way back to each other still feels like unfinished business.
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