Brooke Shields described John F. Kennedy Jr. as 'one of the best kissers'

Brooke Shields and John F. Kennedy Jr. had a brief fling in the 1980s, and she recalled how he gave her “one of the best” kisses of her life.

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Brooke Shields had a brief fling with John F. Kennedy Jr in the 1980s
Brooke Shields had a brief fling with John F. Kennedy Jr in the 1980s

Brooke Shields has remembered John F. Kennedy Jr. as "one of the best kissers".

The 60-year-old actress had a brief fling with the late businessman - the son of former US president John F. Kennedy and Jacqueline Kennedy Onassis - after they met during a skiing trip to Aspen, Colorado, in the 1980s.

In a TikTok video posted on Friday (06.03.26), Brooke's 22-year-old daughter Rowan - who she has with her 61-year-old husband, film director Chris Henchy - lip-synced to singers Taylor Swift, 36, and 33-year-old Charli xcx's live performance of Boom Clap from Taylor's 1989 tour.

And "I wonder if JFK Jr was a good kisser" was typed over the video.

The camera panned past Rowan to Brooke - who also has a 19-year-old daughter called Grier with Chris - as the latter turned over her shoulder as the on-screen text changed to: "One of the best."

During an April 2023 interview on SiriusXM's The Howard Stern Show, Brooke revealed she loved JFK Jr as a child.

She said: "I was so madly in love with him. Since the time I was like three, my mom [Teri Shields] would say, 'That's the boy you're going to marry.'"

Brooke then recalled the time she and JFK Jr met during a skiing trip to Aspen, Colorado.

She said: "We went out. I was invited with the family. He kept saying I looked like his mother, which was really interesting and a compliment. It was also like, 'I don't know how to feel about this.'"

Brooke admitted she was uncertain about going out with a man she had fancied for years.

The star continued: "And then we did have a real date. And I wouldn't sleep with him because I kind of loved him too much."

After the pair enjoyed drinks at a bar with his family, they jumped in a cab back to JFK Jr’s "chalet, hotel that he was in" before they shared a smooch.

Brooke revealed: "He kissed me, and it was like the best kiss I've ever had in my life. 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."

Despite Brooke having crushed hard for JFK Jr, she failed to express her feelings.

She explained: "I froze because it was so precious to me. And 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.'

"I wasn't playing a game. I really was just so afraid of being really hurt, because if I slept with him, I would've given him my entire universe, my heart, my everything."

Asked by Howard, 72, if JFK Jr spoke to her after that moment, Brooke said: "I saw him the next day on the slope, and he didn't look at me, and he didn't talk to me.

"And on the one hand I was like, 'S***!' and on the other hand, I was like, 'Oh, thank God because he still might not have talked to you. Even if you had, and you would've given something that he wouldn't have cared about.'

"And he showed his true colors in that."

However, during the skiing trip, JFK Jr was forced to stay in the house rented by Brooke and Teri.

Brooke shared: "We got stranded. We were all supposed to leave, and we got snowed in. And he had to stay in the house my mom was renting.

"So then it was my mom, John, and me in this chalet, and it was just like, 'This was surreal.'"

However, JFK Jr and Brooke did not utter a word to each other.

Brooke added: "And I think I knew enough about myself by then. I'd been doing work on myself to say, 'You won't be able to handle this, Brooke.'"

JFK Jr went on to find love with publicist Carolyn Bessette, and they got married at the First African Baptist Church in Cumberland Island, Georgia, in September 1996.

But three years later, in July 1999, JFK Jr, 38, Carolyn, 33, and her 34-year-old sister, Lauren Bessette, died in a plane crash off the coast of Martha's Vineyard, Massachusetts.

JFK Jr and Carolyn's romance and tragic deaths has been dramatized in the FX series, Love Story.