There are always those relationships that end up going down in history as some of the most memorable. Ben Affleck and Jennifer Lopez. Sean Penn and Madonna. Janet Jackson and Jermaine Dupri. The list goes on and on. But unfortunately, the running thread between those three relationships is that none of them have lasted. Recently, music producer Dupri sat down with rapper T.I. for the podcast ‘expediTIously’ and opened up about his relationship with Jackson, and how things ultimately ended between the two megastars.
Dupri told T.I. that they two ended up meeting backstage at a concert and ended up flirting through messages between a mutual stylist they shared. Dupri ended up gifting Jackson a two-way pager (yes, this is THAT long ago) after he found out Jackson didn’t have one. They ended up being in contact even more so, eventually falling in love. Dupri shared that their relationship, which lasted eight years, allowed both of the superstars to explore different worlds together—Jackson, Dupri said, was much more sheltered than people would assume.
Dupri went on to explain that because Jackson was brought up in a strictly religious household, she didn’t end up celebrating a birthday until the age of 23. Dupri said, “I took her to Magic City [an Atlanta strip club]. 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.”
Jackson was very much in love with Dupri at the time, even admitting to Oprah in 2010 that Dupri made her feel her best, most comfortable self, even when she was struggling with her body image. Jackson said, “Up until that point, I would still put on a pair of pants, and if my butt looked too big, I didn’t want the pants, as much as I loved them. But it was nine years ago when he said ‘your butt’s fine the way it is.’”
However, despite the fact the couple was in love and together for eight years, things eventually ran its course. The couple split in 2009 and Dupri ended up admitting that it was because of distance. Dupri lived in Atlanta, his hometown, meanwhile, Jackson lived in Malibu, California. Dupri shared “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—k with it. but it ain’t… It’s just something about being here. That stuff didn’t feel like the space where either one of us wanted to be.” Jackson has said of Dupri that he will always remain a lifelong friend.