Why Brooke Shields' College Romance Completely Fell Apart

While Hollywood icon Brooke Shields has been happily married to Chris Henchy since 2001, some of the actor's earlier romances didn't garner such favorable endings. For example, Shields was in a serious relationship with Dean Cain, who you might recognize as the star of "Lois & Clark: The New Adventures of Superman," while the two attended Princeton University in the '80s. The "Suddenly Susan" star talks highly of the bond she shared with Cain, but the relationship was largely affected by tragic aspects of Shields' life, including her complex connection with her mother and her tumultuous relationship with her sexuality.

"He just was so loyal and loving and just so in love," the model told People. "And I did not make it easy." As a known Hollywood figure, Shields also felt the pressures of being a role model to other young women, which further complicated the couple's physical relationship. It was ultimately Shields' need for change and growth that ended the young romance. "I was just sort of growing away from the older me," she said on "The Howard Stern Show." "I was really separating from my mom and really needing to separate from him because he was of a different era in my psyche, you know? And I needed to be challenged differently."

The story behind Brooke Shields' first kiss is extremely controversial, but the "Endless Love" star's first time having sex wasn't exactly smooth sailing either. Shields had a complicated relationship with her sexuality as a young woman, which in turn affected her relationship with Dean Cain. "We had a great relationship, broke up, got back together again after three years," Shields told People. "And that should have been a delicious time for me of reveling in it and feeling proud and free because I was in love." Instead, the model was heavily influenced by guilt, feeling pressure from her faith, her mom, and the public's attention.

In her memoir "There Was a Little Girl," Shields opened up about her first time and how she regrets how much fear and guilt ruled over the experience. "When I was twenty-two, I finally lost my virginity," she wrote. "I did not need [Dean Cain] to prove anything to me, but I was still so bound and guilt-ridden by my mother." The New York native describes her relationship with Cain as full of love and respect, while their first time together was "beautiful." "It should have been what I had wished for myself, but in an instant, guilt slapped me in the face," she said.

Shields recalls bursting into tears and running naked from the bed, only to have Cain chase after her to calm her down. While she explains that she did not regret having sex, Shields was overwhelmed by the intimacy and complicated feelings of guilt. "What should have been the beginning of a wonderful phase in my relationship with Dean turned out to be the beginning of the end," she said. "I suddenly did not know who or how to be around him. It all generated from a twisted sense of self...I could not handle loving somebody more than my mom."