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Jermaine Dupri and Janet Jackson spent nearly a decade together after meeting backstage at her concert in the early 2000s.

After seven years of dating, they called it quits in 2008 but remain one of pop culture’s most intriguing couples.


During a recent interview with rapper T.I. for his podcast expediTIously, Dupri dished about their relationship, including how they met and what caused them to part ways.

“We met at her concert at The Omni [Coliseum]. Kris Kross came… This is when Jermaine Dupri was just a producer. I wasn’t nobody. I didn’t have no record out yet or nothing. Nobody knew me besides what I did for Kris [Kross] and Xscape,” Dupri explained. “We go to her show and I’m part of their entourage… Kris Kross goes in to meet Janet Jackson, and the bodyguard hit me with the hand. So they’re like ‘That’s our man!’ They’re telling her, and when they tell her, she had to vouch for me, ‘Let him in, he cool.’ When I came in, it was almost like the Diana Ross concert. She started talking to me ‘You must be the special one… Why they ain’t wanna leave you outside? Why they didn’t want to leave you outside?’ … It seemed like an energy, right? At that point I was just like, I’m gonna see you again.’ This is Kris time. I’m going to just play my role.”

As noted by MadameNoire, from there, the two began flirting through their mutual acquaintance until the day the flirtation turned into something more serious:


“She realized from that one time that she met me with [Kris Kross] that I was a little bit more important than the person that was supposed to be outside the door. I knew multiple other people. Her friends… and she saw me doing other projects. So we became friends. I guess you wanna call it, I took my shot. And my shot was–she didn’t have a two-way [pager]. They were sending me two-ways like I was the owner… So I found out she didn’t have one and they were sending them to me. I was like, ‘You know what, I want y’all to send one to Janet from me.’ I got her address from her stylist and I sent her the two-way. 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.”

J.D. also shared how he exposed Janet to parts of the culture she hadn’t experienced while living in the “Jackson Bubble”:

“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. You think when a person is that famous, that rich, they know everything. They’ve seen everything. But it was a lot of world that we was living in, 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.”

He then shared how their relationship ended:

“I started seeing so many other things that I wanted to do, and so many other places that I wanted to go. I started thinking like marriage for me wasn’t gonna work. Just, something about it. When you feel like you’re ready to get married, you don’t have no answers, you just know what it is. I was in the space. I’m not gon front and say that I wasn’t. I felt married… I think the only thing that created a difference for me was the fact that we didn’t live together. We had an eight year, nine year relationship, but we didn’t live with each other… I feel like that’s a part where you really determine if you’re strong. She wasn’t willing to move to Atlanta. 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. I wasn’t ready to move to Malibu… I like it, I f*ck with it. but it aint… It’s just something about being here. That stuff didn’t feel like the space where either one of us wanted to be.”

You can listen to J.D.’s interview above. He talks Janet at the 45 min mark.

Really! They Dated?
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