Brooke Shields' dating history: Pretty Baby star's past relationships explored

Brooke Shields is married to TV writer Chris Henchy. (Photo via Getty)
Brooke Shields is married to TV writer Chris Henchy. (Photo via Getty)

Brooke Shields is the person of the hour, thanks to her very revealing documentary, Pretty Baby: Brooke Shields. The two-part docuseries hit Hulu on Monday, April 3, 2023. Helmed by Emmy-winning and two-time Spirit Award-nominated writer/director Lana Wilson, Pretty Baby: Brooke Shields has been named after the 1978 feature Pretty Baby that made Shields a household name, magazine cover girl, and the s*x symbol of the 80s.

Although it sounds like a bullseye, Brooke Shields resented being s*xualized as a young girl, which is what the documentary deals with. As per IMDb, the official synopsis for the documentary series reads:

“[The show] follows actor, model, and icon Brooke Shields as she becomes a woman who discovers her power after being a s*xualized young girl. She shows the dangers and triumphs of gaining agency in a hostile world.”

Apart from showcasing the trauma Brooke Shields suffered due to her sensational imagery in Hollywood, Pretty Baby, the documentary also deals with her personal life and relationships.

Currently married to Chris Henchy, Shields dated quite a few men inside and outside Hollywood before tying the knot with the TV screenwriter in 2001.


Brooke Shields’s personal life was also managed by her mother

1) Rumored affair with Scott Baio

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Baio was a noted star when he met Shields and was clicked numerous times while on dates, but the two maintained in the later years that they were “just friends,” and that the love meetings were all for show.

In one of her memoirs, Shields openly wrote that all her relationships were “orchestrated” by her momager Teri Shields. A section of There Was a Little Girl: The Real Story of My Mother and Me reads:

“She (Teri) didn't focus on romance (never mind love) but instead wanted to associate me with names that connoted fame, money, and power. These were the relationships she supported.”

That’s how she got involved with Baio, John Travolta, Leif Garrett, and John Kennedy, among others.


2) Dean Cain: Lost virginity to her Princeton classmate

Dean Cain, known for Lois & Clark: The New Adventures of Superman, was Brooke Shields’ boyfriend during their Princeton days. They were classmates and Shields said way back in 2009 that she lost her v*rginity to him. She was 22 at the time.

The Blue Lagoon star said that she and Cain were “instantly crazy about each other.” She added in There Was a Little Girl:

“He was incredibly and painfully patient with me regarding s*x…I made him wait and wait and my mom kept track.”

They dated for a couple of years in the 1980s before splitting up.


3) Andre Agassi: A short-lived marriage

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Andre Agassi and Shields started seeing one another in 1993 and were wedded four years later. However, their marriage was nullified in just two years.

Shields credits Agassi for rebuilding her career and helping her maintain distance from Teri, but the relationship developed cracks after her Friends appearance. Initially, they bonded over shared experiences of child stardom and imposing parents, but the actress feels they “should've just been friends.”

However, their dating phase was passionate, since Shields drove a jeep to a remote radio tower while shooting in Africa to fax Agassi, “long letters,” reports stated.


4) Michael Jackson: Friends or lovers?

In Pretty Baby Brooke Shields, the actress points out that they were never in an affair despite Michael Jackson proposing to her numerous times and also wanting to adopt a child with her.

She, however, added in her memoir that they “loved each other,” but it was a non-s*xual one. Shields said in her memoir:

“We just felt safe with each other.”

Terming their friendship/relationship “childlike,” Shields said it was “pathetic” of the late pop sensation to tell Oprah Winfrey in 1993 that they were dating. That’s because she already had a boyfriend at the time.

Despite that, the two always had a blossoming friendship.


5) John Travolta: Another Teri-directed affair

In 1980, John Travolta was a sought-after star, and Teri Shields reportedly played the dating maker between the two. The Grease actor was 27 then and the Endless Love star was 16, and it was a purely platonic relationship.

The couple had a fondness for one another though, and Travolta said Shields is “untainted,” “special,” and that she “exudes goodness.”


6) Liam Neeson: Proposed without a ring

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Shields started dating Taken star Liam Neeson right after her graduation and broke off from Cain. He used wine and poetry to woo her and the young girl was easily “impressed” by him. She said:

“I was so impressed with going out with a real movie star…We got serious after only three months. He asked me to marry him without a ring.”

But their relationship soon lost steam and Liam Neeson married the late British actress Natasha Richardson in 1994.


7) George Michael: “Definitely one-sided,” Shields says

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Shields said that she had a “definitely one-sided” crush on Careless Whisper singer George Michael because he was very “respectful.” Once, while returning from a party hosted by Grace Jones, the late crooner gave her a lift in a limo.

The situation got intense when Michael put a partition between them and the chauffeur, but when it came to a serious point, he retracted and said that his career needs his attention now.

The late crooner came out as gay in 1998.


Watch both parts of Pretty Baby Brooke Shields on Hulu.

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Edited by Vinay Agrawal
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