The secret meeting between Kennedy and Princess Diana is explored in Caroline Hallemann’s new book, “The Kennedys and the Windsors.”
John F. Kennedy Jr. once propositioned Princess Diana at a private meeting held at the Carlyle Hotel in December 1995, but the meeting was anything but romantic.
The late political scion reached out to Diana to ask her if she would be a cover star of his new political lifestyle magazine, George.
“John had brought along with him several ideas for the cover shoot,” writes Caroline Hallemann in her new book, “The Kennedys and the Windsors,” “One featured her wearing a three-corner hat like one from the Revolutionary War, another, oddly enough, showed her in the back of a limousine with the window rolled halfway up, in an attempt to avoid photographers. ”John F. Kennedy Jr. once propositioned Princess Diana in a top secret meeting to be the cover star of his political lifestyle magazine George, according to a new book.
But Diana wasn’t interested in being featured in the new venture. But unfortunately for Kennedy, the princess — who tragically died in a car accident the following year — had already decided she was uninterested in being featured in the magazine before even hearing his ideas.
“She needed the magazine to be a success before she’d publicly front it,” writes Hallemann, “and even with a Kennedy at the helm of the publication, that was hardly a guaranteed prospect. ” Halleman claims Diana told Kennedy: ‘Well, you know, this is all very nice, John. Thank you. But I hope you’ll forgive me if I don’t take up the opportunity this time, but would love to maybe for your 50th or your 100th issue or something.
” When Kennedy got back to the George offices, he allegedly told employees of Diana’s shut down but admitted he was still taken by her this feature on the princess. The royal allegedly told Kennedy, she would “love to maybe for your 50th or your 100th issue or something.
”After being turned down, Kennedy allegedly told staffers Diana “said no,” but “she had a great pair of legs. ”As for why she still chose to take the meeting with Kennedy, one theory is because Diana greatly admired Kennedy for the way he carried himself in the public eye and hoped her eldest son, William — who was just barely a teenager at the time — would adopt some of his admirable qualities.
“I’m hoping he’ll grow up to be as smart about it as John Kennedy Jr,” Diana told magazine editor Tina Brown — who interviewed the princess just weeks before her death — of William, according to her former assistant Patrick Jephson. The late royal is said to have to taken the meeting likely because she admired Kennedy’s handling of the press.
At one point, Diana told a reporter she hoped Prince William would “grow up to be as smart about it as John Kennedy Jr.”Another reason she allegedly wanted to meet with Kennedy — who had been recently named the Sexiest Man Alive at the time — was to make her “The princess’s wish to meet America’s most eligible bachelor owed more than a bit to the fact that he was at the time a particular pin-up of Fergie’s,” Jephson later wrote.during her conversation with playwright Jeremy O. Harris, Bob The Drag Queen, dancer Ivy Mugler, designer Raul Lopez and ID’s Marcello Gutierrez.
The stars briefly dated in the 1980s. Though it wasn’t a romantic meeting, John famously settled down with Carolyn Bessette Kennedy . They were married from 1996 until they tragically died in a plane accident in 1999. .
One of Kennedy’s former close pals described the short-lived romance as “totally a fling” in “JFK Jr.: An Intimate Oral Biography” by RoseMarie Terenzio and Liz McNeil, which came out in 2024.
“Nothing more. Barely a fling at that. ”Tragically, John and Carolyn died in 1999 when John lost control of their small plane. John F. Kennedy Jr. once propositioned Princess Diana in a top secret meeting to be the cover star of his political lifestyle magazine George, according to a new book.
But Diana wasn't interested in being featured in the new venture. The royal allegedly told Kennedy, she would"love to maybe for your 50th or your 100th issue or something.
"After being turned down, Kennedy allegedly told staffers Diana "said no," but"she had a great pair of legs. "The late royal is said to have to taken the meeting likely because she admired Kennedy's handling of the press.
At one point, Diana told a reporter she hoped Prince William would"grow up to be as smart about it as John Kennedy Jr."They were married from 1996 until they tragically died in a plane accident in 1999. .
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