Brooke Shields Shares Memories of a Romantic Ski Trip with JFK Jr. and His Great Kissing Skills
Brooke Shields Remembers John F. Kennedy Jr. as “One of the Best Kissers”
Brooke Shields recently reminisced about her brief romance with John F. Kennedy Jr., describing him as "one of the best kissers." This revelation came during a TikTok video posted by her daughter, Rowan Francis Henchy, on March 6.
In the video, Henchy lip-syncs to Taylor Swift and Charlie XCX’s "Boom Clap," with an on-screen caption questioning Kennedy Jr.’s kissing prowess. She then pans to Shields, who turns with a playful smile, prompting text that reads “one of the best.”
Shields and Kennedy Jr. first met during a ski trip in Aspen, Colorado, in the 1980s. At a lively pub with Kennedy’s family, they snuck away for an impromptu date. "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,’" Shields recalled in a 2023 interview on The Howard Stern Show. Although they never officially dated, their encounter left a significant impression.
Reflecting on their kiss, Shields remarked, "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. He was down to earth and funny and irreverent."
For Shields, who had been smitten with Kennedy since childhood, the brief relationship was unforgettable. "I froze, though, because he was so precious to me," she admitted.
Despite her feelings, Shields set firm boundaries. At the time, she was 19 or 20 and remained a virgin. "I literally said, ‘You so do not want me to lose my virginity to you—because in my world, that means we’re married,’" she shared in JFK Jr.: An Intimate Oral Biography. "I wasn’t playing a game. I really was just so afraid of being really hurt."
By the end of the trip, Shields noted that Kennedy Jr. "didn’t look at me and he didn’t talk to me." Although their fling was brief, she remains fond of the experience and emphasizes the importance of sharing her romantic wisdom with her daughters, Rowan and Grier.
Kennedy Jr. married Carolyn Bessette in 1996 before his tragic death in a plane crash in 1999. Shields’ nostalgic remarks come at a time when interest in Kennedy’s life has resurfaced, particularly with the recent release of the FX limited series Love Story: John F. Kennedy Jr. and Carolyn Bessette.
Shields herself has experienced significant relationships, marrying Andre Agassi in 1997 and later Chris Henchy in 2001. In her memoir, Down Came the Rain: My Journey Through Postpartum Depression, she described first meeting Henchy when he returned her bulldog, Darla, after she strayed away while Shields was at the Warner Bros. lot.
As Shields reflects on her youthful memories with Kennedy Jr., her narrative serves as a reminder of the fleeting nature of early romances and the lasting impact they can have.
