20. Brooke Shields

Brooke Shields attends the Heavenly Bodies: Fashion & The Catholic Imagination Costume Institute Gala at The Metropolitan Museum of Art on May 7, 2018 in New York City.

Unlike numerous stars whose faith was the reason for staying chaste until marriage, Brooke Shields attributes being insecure about her body as the reason she stayed away from sex until 22 years of age.

“I had the public and all this pressure, and I wish I had just gotten it over with in the beginning when it was sort of OK,” she said. “I think I would have been much more in touch with myself.” She had sex with her longtime boyfriend, Dean Cain for the first time several years into the relationship. She thought she’d marry him, but they ended up breaking up.