Brooke Shields Reveals Why She Didn’t Sleep With John F. Kennedy Jr.

Brooke Shields has been raved about as one of the world’s most beautiful women, even before she hit puberty. The 57-year-old Pretty Baby author has dated quite a few bachelors – and had others vying for the chance to call her Mrs., including John F. Kennedy Jr. She had an affinity for him, also, and had the chance to take things all the way but ultimately opted not to. She revealed the details of their multiple encounters during an appearance on The Howard Stern Show, revealing that her team was constantly trying to set her up with whoever was hot and available at the time.

“They were always trying to marry me off to a prince or like John-John,” she said of Kennedy, who was known by public admirers as John-John. “I was so madly in love with him, since the time I was like 3, my mom would say, ‘That’s the boy you’re going to marry, that’s the boy you’re going to marry.’” Years later, she got her chance after she ran into him on a trip to Aspen. She tried to impress him on the slopes, and it didn’t go as planned. She left and needed to be ski-lifted off the mountain. But Kennedy wasn’t turned off. He invited her to an outing with his family at a bar. 

“He kept saying that I look like his mother .. which was interesting and a compliment,” she told Stern. “But I was like, ‘I don’t know how to feel about this..’ And then we did have a real date.” He invited her back to his hotel, where they shared an intimate moment.

“He kissed me, and it was like the best kiss I’ve ever had in my life,” she admitted. “It was beyond not-disappointing. The lips are beautiful, and the face is amazing … and he was down-to-earth and funny and irreverent.” She says he tried to take things to the next level, but she turned him down. “I was so afraid of being really hurt because if I slept with him, I would’ve given him my entire universe,” she said. 

They had a second chance when he had to stay with her in a hotel room briefly during a snowstorm. Still, nothing happened.

“He didn’t look at me, and he didn’t talk to me,” she said. “And on the one hand, I was like, ‘S—,’ and on the other, I was like, ‘Thank God,’ ’cause he still might not have talked to you, even if you had and you would have given something that he wouldn’t have cared about. And he showed his true colors.”

She doesn’t regret her decision. “I think I knew enough about myself by then to say, ‘You won’t be able to handle this, Brooke,’” she told Stern.