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,” per Daily Mail.
“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.”
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.
“Well, she said no,” Kennedy told them. “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.
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“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.
“I want William to be able to handle things as well as John does.”
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 sister-in-law Sarah Ferguson jealous.
“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.
The late royal isn’t the only celebrity once woo’d by the political charmer.
Just last month, Madonna named JFK Jr. as her “best d–k down” 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.
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.”
Kennedy famously ended up with his wife Carolyn Bessette Kennedy, whom he married in 1996. Their tumultuous love story was most recently depicted on the silver screen with FX’s “Love Story,” which premiered in February.
Tragically, John and Carolyn died in 1999 when John lost control of their small plane.
