Maddie Simpson had already spent nearly a decade quietly supporting her boyfriend's music career when the biggest opportunity of his life arrived, playing his own uncle in a billion-dollar biopic. When Michael hit theaters worldwide on April 24, 2026, Simpson stood beside Jaafar Jackson at premiere after premiere, and audiences searching for the actor behind the uncanny transformation into Michael Jackson found themselves asking a second question: who exactly is Maddie Simpson?
Who Is Maddie Simpson, Jaafar Jackson's Fiancée?
Maddie Simpson is an American singer, actress, and social media influencer who has spent years building a music career of her own, separate from her relationship with Jaafar Jackson. According to her Spotify artist bio, her interest in music began early, shaped by a wide range of influences that fed directly into her own work as a singer.
She and Jaafar Jackson, the son of Jermaine Jackson and nephew of the late Michael Jackson, first met as teenagers in 2016. The two made their relationship public within a month of getting together, with Simpson sharing her feelings openly on social media even in those early days, a pattern of visible, unguarded support that has continued through every major milestone of Jaafar's career since. Maddie Simpson's career as a singer has developed quietly alongside that relationship, built on her own Spotify releases rather than any connection to the Jackson family name.
Maddie Simpson's Decade-Long Relationship With Jaafar Jackson
Maddie Simpson and Jaafar Jackson's relationship has now stretched close to ten years, with the couple set to celebrate their tenth anniversary in June 2026. Simpson has marked the milestones publicly and consistently, writing on Instagram for their sixth anniversary in June 2022 that she would never take even a second with him for granted.
Unlike Jaafar, who has said he uses his own Instagram mostly for work, Simpson has never shied away from sharing the more personal side of their relationship, giving fans a rare, ongoing window into a Jackson family relationship that has largely avoided major public drama across nearly a decade together.
Jaafar Jackson Proposes to Maddie Simpson
Jaafar proposed to Simpson with a yellow diamond ring, though the exact date and location of the proposal itself were never publicly detailed. According to reporting from Yahoo News, the couple celebrated their engagement with family and friends at a dinner party in February 2025, confirming to the public that Simpson had officially become Jaafar Jackson's fiancée.
Wedding planning has continued steadily since. Simpson shared a glimpse of dress shopping on Instagram in December 2025, signaling that the couple had moved into active preparations for their ceremony even as Jaafar's career entered its busiest period yet.
Maddie Simpson's Support Through the Michael Biopic
Simpson's role as Jaafar's fiancée took on a much higher public profile once Michael began generating international attention. When the film's trailer dropped on November 6, 2025, it earned 116.2 million views within 24 hours, more views than any musical biopic or concert film trailer in history, according to reporting from CSP Times.
Simpson had been documenting her pride in Jaafar's preparation for the role long before the film's release. In January 2023, more than a year before filming even began, she wrote on Instagram that she had watched Jaafar grow in ways she hadn't known were possible, praising the dedication, focus, love, and care he brought to the role even at that early stage.
Maddie Simpson at the Michael Premieres
Once the film opened in theaters on April 24, 2026, Simpson stood by Jaafar at a string of high-profile premieres. The couple made their red carpet debut together at the film's Berlin premiere on April 10, 2026, and Simpson continued to appear alongside him at subsequent premieres in Gary, Indiana, and Los Angeles, marking some of the most publicly visible appearances of their relationship to date.
Jaafar was also honored during a Michael-related ceremony in Gary, Indiana, in April 2026, receiving the key to the city from Mayor Eddie Melton, a moment that placed Simpson directly in the middle of the Jackson family's continued cultural legacy in his uncle's hometown.
Maddie Simpson in 2026
As of 2026, Maddie Simpson continues pursuing her own music career while supporting Jaafar Jackson through what has become one of the most talked-about years of his life, following Michael's record-breaking box office run past one billion dollars worldwide. With the couple's tenth anniversary approaching in June 2026 and wedding planning already underway, Simpson's relationship with Jaafar remains one of the more stable, long-running partnerships connected to the extended Jackson family.
Maddie Simpson Quick Facts
| Detail | Information |
|---|---|
| Full Name | Maddie Simpson |
| Profession | Singer, actress, social media influencer |
| Partner | Jaafar Jackson |
| Together Since | 2016 |
| Engaged | February 2025 |
| Anniversary | 10 years, June 2026 |
| Fiancé's Uncle | Michael Jackson |
| Fiancé's Film | Michael (2026), grossed over $1 billion |
Frequently Asked Questions
Who is Maddie Simpson?
Maddie Simpson is an American singer, actress, and social media influencer, best known as the fiancée of actor Jaafar Jackson, who portrayed his uncle Michael Jackson in the 2026 biopic Michael.
How long have Maddie Simpson and Jaafar Jackson been together?
The couple met as teenagers in 2016 and will celebrate their tenth anniversary in June 2026. They became engaged in February 2025.
Is Maddie Simpson a singer?
Yes. According to her Spotify artist bio, Simpson is a singer whose love of music began early in life, and she continues to pursue her own music career alongside supporting Jaafar Jackson's acting work.
Did Maddie Simpson attend the Michael premiere?
Yes. Simpson made her red carpet debut with Jaafar Jackson at the Berlin premiere of Michael on April 10, 2026, and also appeared alongside him at premieres in Gary, Indiana, and Los Angeles.
What ring did Jaafar Jackson give Maddie Simpson?
Jaafar proposed with a yellow diamond ring. The exact date and location of the proposal were not publicly disclosed, though the couple celebrated their engagement with family and friends in February 2025.