Brooke Shields hasn’t forgotten her brief fling with John F. Kennedy Jr.
The Suddenly Susan star recently appeared in a short video that her daughter Rowan Henchy posted, reflecting on her dalliance with the son of the 35th president.
“I wonder if JFK Jr. was a good kisser?” the text on the screen reads as Henchy lip-syncs a line from Charli XCX and Taylor Swift’s live performance of “Boom Clap.”
Brooke Shields and Rowan Henchy in New York City on Nov. 12, 2025
Credit: Bryan Bedder/Getty Images for ALICE + OLIVIA
The camera then moves to reveal Shields, who lip-syncs the next line of the song as the text on screen reads, “One of the best.”
Henchy attempted to set the record straight regarding her mom’s romantic history in the caption of the video. “But don’t forget… they never dated,” she wrote.
Shields previously detailed her encounter with Kennedy in a 2023 interview with Howard Stern.
“I was so madly in love with him since the time I was like 3,” she remembered. “My mom would say, ‘That’s the boy you’re going to marry.'”
The model-actress explained that she met Kennedy in the 1980s when she was visiting Aspen, Colo., to attend a wedding. Though she had no experience skiing, she followed him onto incredibly difficult slopes.
“I was like, ‘Sure, I’ll ski down those moguls and a black diamond,’ and [had] never skied before in my life,” she recalled. “I had to get ski-lifted out because I went into the trees. And I couldn’t get off the mountain. And he didn’t help me, but I was like, ‘It’s okay, he can’t help me. He’s John John.'”
Shields then went to a pub with Kennedy’s family. “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,'” she told Stern. “Everybody’s just drinking at the bar, and there’s bar fights and drinking, and he’s like, ‘Do you want to get out of here?’ And I was like, ‘Uh, yeah, I do want to get out of here, John Kennedy.'”
Shields said she went back to Kennedy’s hotel with him. “He kissed me, and it was like the best kiss I’ve ever had in my life,” she continued. “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.”
But Shields said she didn’t sleep with Kennedy. “I wouldn’t sleep with him because I kind of loved him too much,” she recalled. “I froze, though, 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.'”
John F. Kennedy Jr. in New York City on May 19, 1999
Credit: Ron Galella/Ron Galella Collection via Getty
Though Shields thinks Kennedy “absolutely” wanted to sleep with her, she refused. “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.”
The night ended awkwardly, and Shields never spoke to Kennedy again. “I had to get a cab home, which was a little less chivalrous,” she said.
However, Shields continued sharing space with Kennedy even though he didn’t speak to her. “I saw him the next day on the slope, and he didn’t look at me, and he didn’t talk to me,” she said. “He showed his true colors in that. And then 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 and John John and me in this chalet, and it was just like, ‘This was surreal.'”
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Kennedy’s life is back in the spotlight thanks to the new Ryan Murphy FX series Love Story, which stars Paul Anthony Kelly as the late businessman and Sarah Pidgeon as Carolyn Bessette, the fashion publicist whom he married in 1996 before they both died in a plane crash in 1999.
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