The actress dished on the brief moment she had with the late son of John F. Kennedy.
Brooke Shields revealed that it doesn't always pay to meet the man of your dreams. On Tuesday, the 57-year-old Pretty Baby author appeared on The Howard Stern Show and dished on her date with John F. Kennedy Jr.
During the interview, Shields spoke about her high-profile dating life, and admitted that her team was always trying to set her up with the latest "It" boy.
"They were always trying to marry me off to a prince or like John-John," she said of Kennedy, who was affectionately known by the public as John-John.
"I was so madly in love with him, since the time I was like three, my mom would say, "That's the boy you're going to marry, that's the boy you're going to marry.'"
Shields admitted that years later, she would finally get the chance to meet one of America's most eligible bachelors during a trip to Aspen, where she tried to impress him on the slopes and failed.
Following the incident, which left her needing to be ski-lifted off the mountain, Shields said that she was invited by Kennedy for an outing with his family at a rowdy bar. It was there, she said, he began to fill her with compliments.
"He kept saying that I look like his mother .. which was interesting and a compliment," she recalled. "But I was like, 'I don’t know how to feel about this..' And then we did have a real date."
After being around his family at the bar, Shields said that Kennedy asked her, "'Do you want to get out of here?' before they went back to his hotel.
There, the Suddenly Susan actress said she got the best kiss of her life.
"He kissed me, and it was like the best kiss I’ve ever had in my life,” she recounted about their moment. "It was beyond not-disappointing. The lips are beautiful, and the face is amazing … and he was down-to-earth and funny and irreverent."
Shields admitted that although he tried, she did not sleep with him.
"I was so afraid of being really hurt because if I slept with him, I would've given him my entire universe," she said.
Shields claimed he didn't offer her a ride home that evening after she turned down his advances.
"I had to get a cab home, which was a little less chivalrous," she said.
Shields shared that things between her and Kennedy didn't get much better when, at one point, they became stranded together due to a snowstorm and he had to stay with Shields and her mother at their hotel until the weather cleared.
"He didn't look at me and he didn't talk to me," she said. "And on the one hand, I was like, 'S**t,' 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."
In the end, Shields was proud of her decision and sticks by it all these years later.
"I think I knew enough about myself by then to say, 'You wont be able to handle this, Brooke,'" she told Stern.
Kennedy went on to date Sarah Jessica Parker and Cindy Crawford, before he tied the knot with Carolyn Bessette in 1996. Sadly, Kennedy and Bessette died in a plane crash, along with Bessette's sister, in 1999.
Shields went on to marry Andre Agassi, whom she divorced in 1999. The former model is now married to Chris Henchy.