How long did Janet Jackson and Jermaine Dupri date? Split and more explored as Bow Wow says he wants former couple to reconcile

Janet Jackson and Jermaine Dupri's romance stands out as one of the most discussed relationships in early 2000s pop culture. They broke up in 2008.

The couple met backstage at one of Jackson's concerts and started dating in 2002. Their bond grew beyond just a romantic connection over time, with both stars sharing how they shaped each other's lives. He talked about how both their bond on his 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,” he said. “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.”

Dupri renowned for his impact on hip-hop and R&B through his So So Def label, and Jackson, a worldwide star in pop and R&B, formed a connection that ran deeper than their celebrity status. Dupri talked about how he showed Jackson parts of everyday life and Southern culture she hadn't seen before in Atlanta. He noticed that despite her fame, Jackson had lived a somewhat sheltered life, and he took pride in exposing her to "real world" experiences - from visits to well-known spots like Magic City to local eateries. Jackson felt at ease in Dupri's world.

Split rumors and more explored as Bow Wow says he wants former couple to reconcile

People close to the pair say they complemented each other well — Jackson learned to enjoy more relaxed times, while Dupri discovered tranquility in their bond. Their connection spilled over into their work lives too, with Dupri helping to produce Jackson's albums 20 Y.O. and Discipline where she tried out fresh musical styles.

Their romance continued until 2008, though some accounts, including a recent comment from Bow Wow hint at a connection lasting into 2009. Their split stemmed from practical issues their unwillingness to move. Still, whispers of unfaithfulness circulated, with Dupri confessing in Jackson's 2022 Lifetime documentary that he had been "careless," drawing more female attention because he was her boyfriend.

After the breakup, they seem to have maintained mutual respect. They've stayed close, with Dupri showing up in Jackson's documentary to talk about their past. Rapper Bow Wow voiced his hope to see the pair rekindle their love describing Jackson as a caring and unpretentious presence during their time together — someone who could chill with the guys but still radiated elegance and kindness.

"Ms. Jan, man, was everything," Bow Wow said. "You know it was somebody special when the person and the other person break up and you mad at your homie. That's how we all was with JD. Like, 'Damn, man, get it back together, please!"

Though Janet has moved forward in life — she got hitched to businessman Wissam Al Mana and now has a son with him — her lasting connection with Dupri shows how some relationships go beyond just being romantic. Their tale keeps grabbing people's interest because it mixes celebrity status, openness about feelings, and how they've both grown.
 

Gomala Devi is a journalist at Primetimer. 

She holds a Bachelor's degree in Electronics and Instrumentation Engineering and has over three years of experience as a content writer.

Gomala was drawn to writing after reading the Harry Potter series, and she developed an interest in fashion and pop culture at the same time.
She loves exploring the newest developments in the lifestyle space and crafting interesting opinion pieces. She references official websites, interviews, and social media to ensure that her work is factually sound.

In her spare time, she loves to read books and play chess.