Brooke Shields Recalls Running ‘Butt Naked’ From the Room After Losing Virginity to Ex Dean Cain

Brooke Shields revealed that she felt “regret” after losing her virginity to then-boyfriend Dean Cain. In her new Hulu documentary, Shields recalled running “butt naked” from the room. Shields first revealed she lost her virginity to Cain in her memoir, but shared more details in Pretty Baby: Brooke Shields.

In the two-part documentary, Shields recalled the Lois & Clark: The New Adventures of Superman star was “more comfortable with… the sexual part” of their romance than she was, notes Page Six. “I wanted to jump into the personal relationship and the love and the commitment,” Shields explained. “We had to teach each other about each other.”

Shields, 57, did not understand her reaction to having sex at first. However, she now understands she felt “sort of a regret for lost exploration and opportunity to understand my personal sexuality.” She also feels “bad” for her younger self. “She was old enough to own her own body for real. And … just I couldn’t get there at that moment,” Shields said.

Shields wrote about losing her virginity to Cain at 22 years old in her 1985 book On Your Own. Decades later, Shields said she regretted being so open about it. “I mean, I think it was, in hindsight, a bit of a mistake for me to be so open about my virginity because it never left me alone,” Shields said in a November 2022 episode of her Now What? With Brooke Shields podcast.

On Your Own was written by a ghostwriter. After it was published, Shields said she would often get fan mail from kids asking what they should do if their boyfriend was pressuring them to have sex. “My narrative was, ‘You don’t have to do anything you don’t want to,’” Shields said. She also faced “creepy” questions for years from men.

Shields is now married to Chris Henchy, with whom she shares daughters Rowan Francis, 19, and Grief Hammond, 16. She told PEOPLE that neither of them was happy about the Hulu documentary because it included hardships they didn’t know about. “You know I thought I did [teach them], but there’s a lot in the documentary they did not know about with which I got in trouble with them for because they were mad that I didn’t inform them about everything,” she said. “But needless to say, it opened up some other conversations.”

Both parts of Pretty Baby: Brooke Shields are streaming on Hulu. The documentary takes its name from the controversial 1978 movie, in which an 11-year-old Shields played a prostitute. Lana Wilson, who directed Taylor Swift’s Miss Americana, directed Pretty Baby.