One of the great mysteries of life is the relationship between Jermaine Dupri and Janet Jackson. For so long it seemed like an odd pairing. But they were together for so long that it started to make sense. And then, as soon as we were getting used to the idea of them as a couple, they broke up.
And since the two ended their relationship in 2009, after seven years of dating, neither one of them has gone too in depth about what made them split. But during a recent interview with rapper T.I. for his podcast expediTIously, Dupri gave a little insight onto what caused their ultimate split.
But first, he explained how the two met and began dating.
“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. 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.”
From there, the flirtation increased.
“…it became a situation where something that I was doing always kind of bled into her life. I had a stylist that was Janet’s stylist. I used to be joking around like ‘Tell Janet I said… You know what I’m saying.’ And one day, she did the sh*t! ‘J.D. over here talkin…’ And then Janet was saying sh*t back. I’m like wait a minute… I’m not that dude. If you start talking back to me, it’s going to be a different type of game.”
Eventually, 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.”
Before they were a couple, Dupri threw a birthday party for Janet in Miami.
” We was kicking it feel like I made her comfortable being a part of the whole world as opposed to people shunning her because…”
T.I. chimes in to finish the sentence, “she was living in the bubble of the Jacksons.”
J.D. shared that what helped build their relationship was the fact that the two could show each other new things.
“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.”
After T.I. asked how he managed not to get married, he 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 both parts of J.D.’s interview in the videos below. The portion about Janet Jackson begins at the 45 min mark.