Princess Diana and JFK Jr.’s Flirtatious Meeting Revealed 30 Years Later

New details have surfaced about a private 1995 meeting between Princess Diana and John F. Kennedy Jr. at New York’s Carlyle Hotel, where Kennedy hoped to persuade Diana to appear on the cover of his newly launched magazine, George. According to Diana’s former private secretary, Patrick Jephson, the encounter was warm, slightly flirtatious, and carried a sense of anticipation from both sides. Jephson said Diana was “quick-witted and fun to be with,” while Kennedy was respectful and seemed to be seeking reassurance. The two reportedly shared coffee in Diana’s suite and parted on friendly terms.
Kennedy, who had recently been widely admired for his public image, reportedly came prepared with several cover ideas, including one in which Diana would wear a Revolutionary War-style three-corner hat and another showing her in the back of a limousine with the window half-raised to shield her from photographers. Diana ultimately declined the offer, saying she might consider appearing in a later milestone issue, such as the 50th or 100th edition, once the magazine had proven successful.
Jephson later suggested two possible reasons Diana agreed to meet Kennedy. One was that she admired the way he handled fame and public attention, and may have wanted her son Prince William to follow that example. He recalled Diana saying she hoped William would grow up to be “as smart about it as John Kennedy Jr.” Another theory was more personal: Jephson said Diana may have wanted to make her sister-in-law Sarah Ferguson jealous, since Kennedy was reportedly a favorite of Ferguson’s.
The meeting and its aftermath are described in more detail in Caroline Hallemann’s new book, The Kennedys and the Windsors. Hallemann writes that Diana needed George to establish itself before she would agree to appear on its cover, especially given that even a Kennedy-led publication offered no guarantee of success. She also reports that Kennedy later told his staff, after learning of Diana’s refusal, “Well, she said no. But she had a great pair of legs.”
George magazine launched in 1995 and ran until 2001. At the time of the meeting, Diana was still married to Prince Charles, though the couple would divorce in 1996 after having two sons, Prince William and Prince Harry. Diana died in a car crash in Paris in 1997. Kennedy was dating Carolyn Bessette in 1995; they married in 1996 and died together, along with Bessette’s sister Lauren, in a plane crash in 1999.



