According to a new book, John F. Kennedy Jr. privately met Princess Diana at the Carlyle Hotel in December 1995 to ask whether she would appear on the cover of his new political lifestyle magazine, George. The meeting, however, was not romantic and was instead focused on a possible magazine feature that Kennedy hoped would bring attention and credibility to the publication. Author Caroline Hallemann writes in The Kennedys and the Windsors, as reported by the Daily Mail, that Kennedy arrived with several ideas for a cover shoot, including one in which Diana would wear a Revolutionary War-style three-corner hat and another showing her in the back seat of a limousine with the window halfway up, supposedly to help her avoid photographers.
Diana was reportedly uninterested in the offer before even hearing the full presentation. Hallemann writes that she believed the magazine needed to prove itself before she would publicly associate with it, and that even Kennedy’s famous name did not guarantee its success. According to the book, Diana responded politely, telling Kennedy that while the idea was nice, she could not accept at that time, though she jokingly suggested she might consider it for a later anniversary issue, such as the 50th or 100th edition.
After returning to the George offices, Kennedy allegedly informed his staff that Diana had declined the offer but still admired her appearance. He is quoted as saying that although she said no, she had “a great pair of legs.” The anecdote adds to the long-running fascination with both Kennedy and Diana, two of the most photographed and highly scrutinized public figures of their era.
The book also suggests possible reasons Diana agreed to the meeting. One was her admiration for Kennedy’s skill in managing public attention. According to her former assistant Patrick Jephson, Diana told editor Tina Brown that she hoped her eldest son, Prince William, would grow up to handle publicity as well as Kennedy did. She reportedly wanted William to be as smart about fame and the press as JFK Jr. Another theory is that Diana wanted to meet Kennedy partly because Sarah Ferguson, the Duchess of York, was said to be especially interested in him at the time, and Diana may have enjoyed the social intrigue.
Kennedy was widely regarded as one of America’s most eligible bachelors during the 1990s and had already become a media figure in his own right. The article also notes that Madonna recently referred to him as her “best d–k down,” underscoring the continuing public interest in his brief romantic history. Kennedy had previously dated Madonna in the 1980s, but those accounts describe the relationship as a short fling rather than a serious romance.
Kennedy later married Carolyn Bessette in 1996, and the couple became one of the most closely watched pairs of the decade. Their marriage ended tragically in 1999 when both died in a plane crash after John lost control of the aircraft. The story of JFK Jr. and Carolyn was recently revisited in FX’s Love Story, highlighting the lasting cultural memory of the couple and the era in which they became icons.
