Brooke Shields has been linked to a number of prominent men over the years, but her first high-profile romance was with actor Dean Cain while she was in college. When the future “Lois & Clark: The New Adventures of Superman” star was a student at Princeton University in the 1980s, she dated the “Pretty Baby” beauty, but her popularity — and some deeply rooted shame — led the romance to fizzle.

Shields had been in the spotlight since he was a toddler. She was sexualized early on in her career, which was heavily curated by her mother, Teri, with photoshoots that would not fly today and a contentious portrayal as a 12-year-old prostitute in Louis Malle’s 1978 film “Pretty Baby.” In real life, though, she was open about her virginity, even into her college years.

In her 1985 book “On Your Own,” Shields revealed that she was still a virgin at age 20. Years later, during an episode of her podcast, “Now What? With Brooke Shields,” the star admitted that she regretted publicly opening up about her virginity. “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,” she said. “I became the most famous virgin in the world.”

And it was that title, as well as her mother’s insistence that she keep her virginity, that brought her first love relationship with Cain to an end.

Brooke Shields felt ashamed when she lost her virginity to Dean Cain.

Brooke Shields

Brooke Shields’ mother exercised total control over her daughter’s career. Teri, the ultimate stage parent, wanted her daughter to be perceived in a certain way. Teri had no problem with Shields’ hot Calvin Klein advertising, but she had a problem with real-life sex. Shields claimed in her 2014 memoir, “There Was a Little Girl: The Real Story of My Mother and Me,” that her mother was critical of her relationship with Dean Cain. “She had faith in me to keep my chastity vow,” Shields wrote. Cain, she said, was incredibly patient with her when it came to sex. “I made him wait and wait, and my mum kept track,” she explained.

So, when Shields finally did lose her virginity, she felt ashamed. In the 2023 Hulu documentary “Pretty Baby: Brooke Shields,” Shields revealed she immediately regretted consummating her relationship with Cain. “When we finally had sex, I immediately ran out of the room down the hall butt naked, just running. I didn’t know where I was going,” Shields said in the documentary. She added that Cain chased after her with a duvet in his hand and assured her that nothing had changed.

But for Shields, everything changed. In her book, she noted that her mother’s obsession with her virginity was not just due to their Catholic faith. “I believe she wanted me to stay hers alone,” Shields wrote. “She believed in an absolute hold she had on me … And growing up, and having sex, would mean that I was leaving her.”

Brooke Shields apologized to Dean Cain for how she acted during their relationship.

While she regretted the way the end of her virginity played out, Brooke Shields said her overall relationship with Dean Cain was wonderful. “He just was so loyal and loving and just so in love. And I did not make it easy,” she told People in March 2023.

She also shared that she later apologized to Cain for how she let the guilt of letting her mom and her fans down ultimately affect their relationship. “I said, ‘I’m sorry for you, and I’m really sorry for me,'” she revealed of her conversation with her ex-boyfriend years later.

For his part, Cain didn’t mind that Shields named him in her book and shared details of their awkward first time. In an interview with Fox 411, the actor said, “Brooke was a very big part of my life, and I’m honored to have been a part of her life.” But he did downplay the narrative that his ex “lost” something to him. “I don’t think a girl loses her virginity. They give it,” Cain told Us Weekly in 2014. “I mean, we were in love. She was a wonderful girl.”