Michael Jackson, known as the King of Pop, was a figure whose fame and influence extended far beyond music. His personal life, especially his relationships with women, has always been a topic of intrigue. Despite the controversies surrounding him, Michael was a man with a deep passion for love and affection, and his romantic life was as captivating as his musical career. Let’s take a closer look at the top 10 women Michael Jackson dated throughout his life.

10. Tatum O’NealTatum O’Neal, an Oscar-winning actress, was Michael Jackson’s first-ever romantic partner. The two met when Tatum was just 12 years old, and Michael was 17. They developed a connection over time, and a few years later, their relationship blossomed. However, in 1982, Michael stated that their relationship had faded, and they chose to remain friends. Though their romance didn’t last, it marked the beginning of Michael’s involvement in high-profile relationships.

9. Stephanie MillsBefore her connection with Michael, Stephanie Mills had already made a name for herself as the star of The Wiz, the iconic musical. Diana Ross would eventually take over her role for the film adaptation, but by then, Mills had already started dating Michael. She recalled in a 2015 interview that Michael often brought her to film sets during their relationship. The two shared a brief but meaningful connection that remains part of Michael’s early romantic history.

8. Diana RossDiana Ross was one of Michael Jackson’s most well-known romantic interests. The two had an on-and-off relationship, often discussed in Michael’s brother Jermaine’s book You Were Not Alone. According to Jermaine, Michael frequently referred to Diana as his girlfriend and was even ready to marry her, despite their 15-year age difference. However, Diana wasn’t comfortable with this gap, and their relationship eventually ended, though they remained close for years.

7. Brooke ShieldsBrooke Shields and Michael Jackson’s connection began at the 1981 Academy Awards. Their relationship quickly grew, and the two spent considerable time together. At one point, they even discussed marriage, but Brooke wasn’t interested in tying the knot at the time. She later explained in a 2009 interview with Rolling Stone that Michael had her for the rest of his life, and that didn’t require a formal marriage.

6. Tatiana ThumbtzenTatiana Thumbtzen is best remembered as the woman who appeared alongside Michael in the music video for The Way You Make Me Feel. Their chemistry on-screen quickly transitioned into a real-life romance. Tatiana claimed that their relationship went beyond the video, and the two shared many passionate moments. Unfortunately, their romance ended after one of Michael’s tours, leaving fans to wonder about what could have been.

5. Madonna
One of Michael Jackson’s more publicized but short-lived relationships was with the Queen of Pop, Madonna. They only went on a few dinner dates, but their time together stirred massive media attention. Madonna herself confessed that she kissed Michael with a French kiss and got him to loosen up with a glass of Chardonnay. Despite the brief nature of their relationship, their time together was enough to capture the media’s attention and fuel rumors of a possible romance.

4. Shana Mangatal
Shana Mangatal rose to fame after publishing Michael and Me: The Untold Story of Michael Jackson’s Secret Romance, a confessional book that claimed she had a romantic relationship with Michael Jackson. While the claims were controversial and widely debated, Shana’s book added to the intrigue surrounding Michael’s love life. Despite the backlash she received, Shana continues to be linked with Michael through her book and the stories she shared.

3. Whitney Houston
Whitney Houston, another music legend, was rumored to have had a brief fling with Michael Jackson. In 2012, Michael’s former bodyguard, Matt Fitz, appeared on The Today Show and revealed that Michael and Whitney had a short but intense romance. According to Fitz, Whitney moved into Neverland Ranch at one point, and Michael even considered marrying her. Their relationship, however, was fleeting, as both stars were busy with their respective careers.

2. Lisa Marie Presley
Lisa Marie Presley, the daughter of Elvis Presley, had one of the most publicized and iconic relationships with Michael Jackson. The two met when Michael was 16, and Lisa was just six, but their connection didn’t blossom until much later. They became friends and eventually got married in a private ceremony in the Dominican Republic in 1994. Their marriage lasted for two years before they divorced, with major disagreements being cited as the cause of their split. Despite the short duration, their relationship remains one of Michael’s most talked-about.

1. Debbie Rowe
Debbie Rowe, Michael Jackson’s dermatologist’s assistant, holds the title of being Michael’s most significant romantic partner, as she is the mother of his two children, Prince and Paris. Michael and Debbie met during one of his regular visits to the dermatologist, and their friendship quickly blossomed into a romantic relationship. After Michael’s separation from Lisa Marie Presley, Debbie offered to carry his child, which led to her becoming pregnant with his first son. The two later got married and had another child before divorcing. Debbie’s relationship with Michael was key in the creation of his family, and she remains an important figure in his personal life.

Conclusion
Michael Jackson’s relationships were often as complex and intriguing as his music. From his early romance with Tatum O’Neal to his controversial marriage to Lisa Marie Presley, Michael’s love life was filled with fascinating moments that captivated the public. His connections with women, whether brief or lasting, were part of the legend that continues to define the King of Pop’s legacy. As much as his music shaped the world, his romantic relationships were a testament to his humanity and vulnerability.