Who Did Brooke Shields Date? All Dating History Of Brooke Shields

Sunny Anderson
Apr 04, 2023
Apr 04, 2023

Brooke Shields has been open and honest about her personal life, particularly her past romances, through a 2014 tell-all book and a 2023 documentary. Before marrying Chris Henchy in 2001, the actress was connected to Michael Jackson, John Travolta, and Liam Neeson. The couple has two daughters together.

#1. Who has Brooke Shields dated?

Who did Brooke Shields date Source: Netflix Life

In her memoir The Real Story of My Mother and Me, Brooke Shields disclosed that her relationship with Scott Baio in the late 1970s, as well as her later romances with John Travolta, Jimmy McNichol, Leif Garrett, and John F. Kennedy Jr, were all just for show. She explained that her mother, Teri Shields, had a hand in orchestrating her public dating life.
She remembered: "These were the relationships she supported.
"Basically, my 'relationships' had always been orchestrated by my mother in one way or another. "She didn't focus on romance (never mind love) but instead wanted to associate me with names that connoted fame, money, and power." For two years sometime between 1983 and 1987, Brooke dated fellow Princeton University student and actor Dean Cain.

#2. Brooke's first husband had major trust issues.

Brooke Shields marriage Source: Parade

If you want to move on from a movie star, you might try finding a famous tennis player instead! Brooke and Andre Agassi's relationship began in 1993 and they tied the knot in 1997. However, Andre had acted jealously prior to their marriage, destroying his tennis trophies after seeing Brooke in her cameo role on Friends, as reported by The Daily Mail.
Andre later admitted to Brooke that he had been struggling with addiction. He admitted in his own memoir that their marriage had been a mistake as well. Brooke and Andre divorced after two years of marriage.
Related: Who Sexually Assaulted Brooke Shields?

#3. Brooke and Dean Cain

Brooke and Dean Cain Source: MEAWW

Before he was Superman on Lois & Clark, Dean Cain was Shields' football player boyfriend and classmate at Princeton. "We were crazy about each other," she said of the man she dated for two years and lost her virginity to. "He was incredibly and painfully patient with me regarding sex. But even when Mom wasn't around, I felt as if she was watching." In a 2023 cover issue for PEOPLE, Shields discussed her regrets about the way things ended between the two, saying she was "paralyzed from shame" and how she apologized to Cain years prior. "I said, 'I'm sorry for you, and I'm really sorry for me,' " she said.

#4. Did Brooke date Michael Jackson?

Did Brooke date Michael Jackson Source: The Outlet

Shields and Jackson first encountered each other when Shields was 13 and Jackson was 19. Despite not having a romantic relationship, the two created an atmosphere of comfortability and support. Shields said, “We just felt safe with each other. We watched movies, ate candy and laughed at the chaos around us. We had a deep love for each other that wasn’t romantic.” Jackson even gifted Shields a ring when they first met.
They developed a close bond throughout the years, and Jackson even took her as his date to Elizabeth Taylor's 1991 wedding. Shields revealed in her 2023 documentary Pretty Baby that she and Jackson had a falling-out once he claimed they were dating on The Oprah Winfrey Show. After the King of Pop died in June 2009, Shields was asked by Jackson's mother to speak at his memorial.
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