There are a few romances that sometimes give the public pause, and when Jermaine Dupri and Janet Jackson came forward as a couple, people struggled with understanding the pairing. It makes sense why the two artists would link up, but in the early 2000s, people couldn’t believe that Dupri was able to seal the deal with one of the most famous singers in the world who was also from one of the most notable musical families.

Jermaine Durpi, Janet Jackson
Carlo Allegri / Staff / Getty Images

The topic of Dupri’s seven-year relationship with Janet Jackson came up in conversation during the So So Def mogul’s interview with T.I. on ExpediTIously. Even Tip admitted that when he heard that Jermaine Dupri had locked things down with Ms. Jackson, he couldn’t believe it. Jermaine revealed that he and Janet first met at a Kriss Kross concert and later they all attended one of her shows. This was before he was the hitmaker that he is today, and he was seen as just a member of Kross Kross’s entourage.

Dupri and Janet knew a few of the same people and Jermaine said that he would joke around with a stylist and say flirtatious things about the singer. One day, the stylist called his bluff and got Janet on the phone, and as the stylist was talking to J.J., she dropped a few flirtatious remarks of her own. It took J.D. by surprise, but the two began to talk seriously, and it led to the them dating between 2002 to 2009.

Watch Jermaine Dupri share details of his romance with Janet Jackson around the 46:30 mark below.