Did Michael Jackson Date Brooke Shields? The Rumors, Explained

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At about five years old, before many children can read, Michael Jackson was already performing with his brothers in the Jackson 5. When he was just 10, the band signed to Motown Records, and, at 11, Jackson had his first #1 single, "I Want You Back." From that moment on, Jackson's life would happen in front of the public eye, and an endless number of myths would grow around him. However, one of the stranger myths about Jackson was started by the King of Pop himself — the rumor that he dated Brooke Shields.

The rumor really took off in 1993, when Michael Jackson was interviewed by Oprah Winfrey. She asked the iconic singer, among other things, if he had ever been in love and if he was a virgin. While Jackson refused to discuss his sex life, he did say that he had been in love with two women, and Shields was one of them. In fact, he even claimed to be dating her at the time, which came as a surprise to Shields.

Yes, Shields had no idea at the time that Jackson thought they were in a relationship. She discussed her surprise with The Times in 2023, revealing that she called Jackson and told him, "This is kind of pathetic that you need to do this. I am having a shot at normal life — you cannot drag me into crazy town." 

Shields also opened up about the infamous photo of Jackson kissing her in the backseat of a car. She told The Times, "There was one moment when we were in the car and the cameras were there and he grabbed me to kiss me and I said, 'No! Stop! We are just friends and you need me as a friend.'" While Jackson tried to build a mythology about his romantic relationship with Shields, the truth was that they were just close friends for a long time. It was a strange friendship, though.

Brooke Shields has stated that she met Michael Jackson when she was 13, making him about 20 at the time, and they became fast friends. After Jackson's death, Shields wrote about their friendship for Rolling Stone, admitting, "Everybody was confused by our relationship." For her, it made perfect sense.

To Shields, Jackson was someone who was older, but who also grew up in the spotlight and could understand the tragedies Shields had to deal with as a child star. For Jackson, Shields was someone who wasn't trapped in their fame and was able to experience normal things, such as her college romance with Dean Cain, and then tell him all about it. Jackson would ask Shields about her romances in childlike terms, asking about what each "base" was when it came to sex. For him, Shields explained to Rolling Stone, it was something he never had a chance to experience, since he grew up in a bubble. At Jackson's memorial, Shields described how fame made them both grow up faster than they should have, but together, they could be their true selves.

In her autobiography, "There Was a Little Girl," Shields described how the pair made each other feel safe. They would spend time together watching movies and eating junk food, but it was never romantic, even if Jackson would often ask her to marry him or raise children with him, like a little child play-dreaming about the future. While Shields had no interest in marrying the King of Pop and raising a family with him, Jackson did have three children, with his life eventually going in a different direction from Shields'. The last interaction between the two of them happened in 2003 when her father died. Shields spoke about it in 2018 on "Watch What Happens Live," revealing that Jackson sent her a floral arrangement.