Brooke Shields says John F Kennedy Jr was the ‘best kiss I’ve ever had in my life’

The actor says JFK Jr ‘showed his true colors’ after she rejected him on the first date

Brooke Shields revealed John F Kennedy Jr was the best kiss she’s ever had, and how he became “less than chivalrous” after she turned him down on the first date.

On 4 April, the actor and model appeared on SiriusXM’s The Howard Stern Show to promote the release of her new documentary, Pretty Baby: Brooke Shields. While speaking with host Stern, Shields shared details about her short-lived romantic encounter with the eldest son of President John F Kennedy and Jackie Onassis.

“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,’” the 57-year-old explained.

Decades later, Shields finally met JFK Jr – nicknamed “John-John” – during a trip to Aspen, Colorado, with her mother, where the Kennedys were staying. The Blue Lagoon star recalled trying to impress her childhood crush on the slopes, despite having never skied before.

“I had to get ski-lifted out because I went into the trees,” she said. “And he didn’t help me, but I was like, ‘It’s okay. He can’t help me. He’s John-John.’”

Shields continued: “He kept saying I look like his mother, which is really interesting, and a compliment, [but] I was like, ‘I don’t know how to feel about this.’ And then we did have a real date.”

The model was then invited to join Kennedy and his famous family at a local rowdy pub, filled with bar fights and drinking. At one point in the evening, the attorney turned to Shields: “He said, ‘Do you want to get out of here?’ And I was like, ‘Uh, yeah, I do want to get out of here, John Kennedy.’”

The pair went back to the “chalet hotel” where Kennedy was staying, where he made a move on the Hollywood star.

“He kissed me, and it was like the best kiss I’ve ever had in my life,” she shared. “It was beyond not-disappointing. The lips are beautiful, the face is amazing, and the body and the person.”

But when he tried to take things a step further with Shields, she rejected his sexual advances.

“I wouldn’t sleep with him because I kind of loved him too much,” she told Stern. “I froze though because it was so precious to me. I was like, ‘Oh my god, you’re falling in love and if you sleep with him he may not talk to you again and you can’t handle that.’”

Shields added that she “was so afraid of being really hurt” if she had slept with him, so she decided to protect her heart instead. Their date was cut short after she turned Kennedy down and she had to make her own way back home.

“I had to get a cab home, which was a little less chivalrous,” she joked.

The following day, Shields remembered being ignored by Kennedy on the slopes after their awkward date.

“He didn’t look at me and he didn’t talk to me,” she recalled. “On the one hand, I was like ‘shit!’ On the other hand, I was like, ‘Thank God’.”

She added: “He showed his true colors in that.”

John F Kennedy Jr in May 1989 (AFP via Getty Images)

John F Kennedy Jr went on to date a number of famous women – including Sarah Jessica Parker, Cindy Crawford, and Daryl Hannah – before marrying Calvin Klein publicist Carolyn Bessette. The socialite couple tied the knot in 1996, but tragically died on 16 July 1999 when their plane crashed into the Atlantic Ocean near Martha’s Vineyard, Massachusetts.

Meanwhile, Shields has been married to husband Chris Henchy for 22 years. They share daughters Rowan Francis Henchy, 19, and Grier Hammond Henchy, 16.

In her new Hulu documentary, which began streaming on 3 April, Brooke Shields opens up about the exploitation and sexualisation she experienced as a child star – including being sexually assaulted in her 20s by an unnamed Hollywood executive, posing nude for Playboy at the age of 10, and having her first kiss with a 29-year-old actor when she was just 11.