Brooke Shields Reveals Moment John F. Kennedy Jr. Showed His True Colors

April 6, 2023
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When Brooke Shields met John F. Kennedy Jr., she had one of the best moments of her life ― before the famed playboy showed his “true colors.”

In an appearance on “The Howard Stern Show” on Tuesday, Shields candidly recalled meeting the son of President John F. Kennedy and Jacqueline Kennedy Onassis during a trip to Aspen, Colorado.

At the time, Shields said, she had been “so madly in love” with the younger Kennedy “since the time I was like 3” that her mother routinely said, “That’s the boy you’re going to marry.”

So she was a little star-struck when she crossed paths with the young scion while visiting the ski town for a wedding.

“He kept saying I looked like his mother, which was really interesting and a compliment,” Shields told the radio host. “I was also like, ‘I don’t know how to feel about this.’ And then we did have a real date.”

Kennedy took the Hollywood star to a pub with his family, and it erupted in “bar fights,” prompting their exit, she said.

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[youtube https://www.youtube.com/watch?v=3-wVonBibxY?rel=0&enablejsapi=1]

“We went back to this chalet hotel that he was in,” Shields recalled. “He kissed me, and it was the best kiss I’ve ever had in my life. It was beyond not-disappointing. The lips are beautiful, the face is amazing, and the body and the person.”

“And he was down-to-earth and funny and irreverent,” she continued. “I froze, though, because he was so precious to me. I was like, ‘Oh, my God, you’re falling in love.’”

Shields recalled wanting to protect herself, she told Stern, so despite the direction things were going, she decided not to sleep with Kennedy that night.

“I had to get a cab home,” she said with a laugh, “which is a little less than chivalrous.”

It was the next day when Kennedy “showed his true colors,” Shields said.

When she saw him on the slopes, she recalled, “he didn’t look at me, and he didn’t talk to me.” The actor was ultimately relieved, she said, because she realized Kennedy might have ignored her just the same if she had decided to sleep with him the previous night.

Kennedy and his wife, Carolyn Bessette-Kennedy, died in a plane crash on July 16, 1999.
Kennedy and his wife, Carolyn Bessette-Kennedy, died in a plane crash on July 16, 1999.

Ron Galella via Getty Images

Kennedy went on to date and marry Calvin Klein publicist Carolyn Bessette. They became one of the most celebrated socialite couples in New York, but tragically died on July 16, 1999, when Kennedy crashed their plane into the Atlantic near Martha’s Vineyard.

Shields, who married director Chris Henchy in 2001, is currently promoting a documentary about her life, “Pretty Baby: Brooke Shields,” which is now streaming on Hulu.

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