Brooke Shields Shares Rare Memories of Whirlwind Romance With John F. Kennedy Jr.

Brooke Shields is opening up about her romance with John F Kennedy Jr., nearly 40 years after the two met and began a short romance.

During an appearance on Watch What Happens Live With Andy Cohen, Shields explained that they dated, saying that she "didn't have a love story, I had a crazy, crazy crush."

"We dated, but I never slept with him, so I don't know if that counts," she added. "He was lovely to me."

The two met on a skiing trip in Aspen, Colorado. This is not the first time Shields mentioned her brief romance with Kennedy Jr., detailing how the two shared a kiss during an appearance on The Howard Stern Show in 2023.

"He kissed me, and it was like the best kiss I've ever had in my life," she said. "It was beyond not-disappointing. The lips are beautiful, and the face is amazing, and the body and the person, and he was down to earth and funny and irreverent."

Brooke Shields Was A Big Fan of 'Love Story'

While speaking with Cohen, Shields also revealed that she binged all of Ryan Murphy's TV show Love Story, which followed Kennedy's relationship with his wife Carolyn Bessette Kennedy.

"I watched it start to finish," she said. "I loved it. I thought the acting was amazing."

In a recent interview with PEOPLE, Shields further detailed how her daughter, Rowan, worked on the show as a production assistant and called her mom to warn her that she would be mentioned on the hit show.

"That was a little weird," Brooke recalled. "I was away, and my daughter called me and she says, ‘Oh my God, you're mentioned in Love Story,' and she's like, ‘Is it true?'"

"I was like, ‘OK, I'd be happy to tell you all the stories if you want,'" she added of the conversation, "‘but-yes.'"

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This story was originally published May 22, 2026 at 10:38 AM.