Jaafar Jackson's Decade-Long Romance: Inside His Relationship With Singer Maddie Simpson

As Jaafar Jackson embarks on his acting career playing his late uncle Michael Jackson in the upcoming film Michael, he's had a steady source of encouragement by his side: his longtime partner.

The 29-year-old performer, son of Jermaine Jackson, is stepping into the world of acting for the first time with the project, which received full backing from the Michael Jackson estate and the majority of his family members. His grandmother Katherine Jackson voiced her enthusiasm for the casting, stating, "Jaafar embodies my son. It's so wonderful to see him carry on the Jackson legacy of entertainers and performers."

Behind the scenes of this major career milestone is singer Maddie Simpson, with whom Jaafar has been in a relationship since 2016. The couple will reach their ten-year dating milestone in June 2026.

Simpson, a musician in her own right, has spoken about her artistic journey in previous interviews. She shared her perspective with Schon! Magazine, explaining, "I think the biggest thing that has drawn me to music is just connecting with people through music. There wasn't really ever a moment of realization that I wanted to pursue music professionally, because for as long as I can remember, there's was nothing else I could see myself doing."

When Jaafar's role in Michael was announced in January 2023, Simpson took to Instagram to celebrate his achievement. "Over the past year and a half I have watched Jaafar grow in ways I didn't know were possible. The dedication, focus, love and care he has put into this role already is truly unparalleled. Not only has he proven that he is more than capable of taking on this responsibility to others, he has most importantly proven it to himself. His uncle Michael is ever-present. He is undoubtedly guiding Jaafar through every single step of this process," she wrote.

She continued, "The admiration and respect I have for Jaafar is genuinely impossible to put into words. Saying I am proud of him falls short of all of the emotions I feel. I love him so dearly and I can't wait for the world to see how exceptional he is."