Brooke Shields Says JFK Jr. Was 'One of the Best' Kissers After Aspen Encounter in the 1980s

Brooke Shields has stirred nostalgic interest in one of Hollywood's most discussed yet fleeting romances, recalling a youthful encounter with John F. Kennedy Jr. in the 1980s.

The actress and model, now in her late 50s, jokingly remembered her youthful encounter with John F. Kennedy Jr., calling him 'one of the best' kissers in a playful video shared on social media.

The clip comes as Kennedy's life is back in the spotlight thanks to Love Story, a new FX series about his relationship with Carolyn Bessette before his tragic death in 1999.

A Playful Look Back at an Aspen Romance

Shields, best known for roles in films and television, including Suddenly Susan, reflected on her brief romantic moment with JFK Jr. in a video posted by her daughter, Rowan Henchy, on TikTok.

In the clip, Henchy lip‑syncs to text asking, 'I wonder if JFK Jr. was a good kisser?' before the camera moves to Shields, who mouths the words 'One of the best.'

Henchy was careful to clarify that the pair 'never dated,' reminding viewers that their connection was a fleeting moment from Shields' youth rather than a long‑term romance.

How the Meeting Started — and Why It Ended

Shields previously recounted the origins of her encounter with Kennedy during a 2023 interview with Howard Stern.

She explained that she met him at a wedding in Aspen, Colorado, when she was in her late teens or early twenties. Despite having little skiing experience, she agreed to follow Kennedy onto challenging slopes, only to struggle and be rescued by a ski lift after falling into the trees.

Although the day began awkwardly, the evening progressed to a pub outing with Kennedy's family. Shields recalled that Kennedy repeatedly told her she looked like his mother—a remark both flattering and strange to her—before inviting her to leave with him. They returned to his hotel, and the two shared a kiss that Shields described as unforgettable.

She told Stern that the kiss was 'beyond not‑disappointing' and that Kennedy was charismatic, funny, and 'down‑to‑earth.' Despite this connection, Shields said she chose not to sleep with him, fearing emotional hurt and valuing the moment too much to risk changing it.

Her hesitation, she said, was driven by youthful emotion: 'If I slept with him, I would've given him my entire universe,; she said, illustrating how deeply she felt the moment even at such a young age.

Kennedy's Romantic Life Revisited

John F. Kennedy Jr.—known affectionately as 'John John'—was the son of President John F. Kennedy and Jacqueline Kennedy Onassis.

Often called 'America's most eligible bachelor' long before he married Carolyn Bessette in 1996, his romantic life attracted public attention during the 1980s and early 1990s. Before Carolyn, he had a series of relationships and high‑profile links with several women.

In his late teens and early adulthood, he dated Sally Munro for about six years while at Brown University, and then had a serious relationship with classmate Christina Haag for around five years. Later, he was romantically involved with actress Daryl Hannah for over five years in the late 1980s and early 1990s.

He also had shorter romances or links with Brooke Shields, as well as relationships with Sarah Jessica Parker, and was at times associated with models like Julie Baker and Cindy Crawford.

Kennedy's life and relationships have once again captured public imagination thanks to the recent FX series Love Story, which explores his marriage to Bessette before his untimely death in a plane crash in 1999, along with his wife, Carolyn Bessette, and her sister.

The tragedy marked one of the most-watched and mourned events of the late 20th century.