John F. Kennedy Jr. once proposed to Princess Diana in a private meeting held at the Carlyle Hotel in December 1995, but the meeting was anything but romantic.
The late political scion approached Diana to ask if she would become the cover star of his new political magazine, George.
“John brought with him many ideas for the cover shoot,” Caroline Halliman writes in her new book, The Kennedys and the Windsors. Per the Daily Mail.
“One photo showed her wearing a tricorn hat like one from the Revolutionary War, and another showed her, oddly enough, in the back of a limousine with the window halfway down, trying to avoid photographers.”
But unfortunately for Kennedy, the princess — who tragically died in a car accident the following year — had already decided she was not interested in appearing in the magazine even before she heard his ideas.
“She needed the magazine to be a success before she could front it publicly, and even with Kennedy at the helm, that was not a guaranteed possibility,” Halliman wrote.
“Well, you know, it’s all very nice, John,” Halliman claims Diana told Kennedy. Thank you. But I hope you’ll forgive me if I don’t take this opportunity this time, but I’d like to maybe the fiftieth or the hundredth or something like that.
When Kennedy returned to George’s offices, he allegedly told staff to shut Diana down but admitted he was still taken by that quality about the princess.
“Well, she said no,” Kennedy told them. “But she had a wonderful pair of legs.”
As for why she chose to have the meeting with Kennedy, one theory is that Diana greatly admired Kennedy because of the way he presented himself in the public eye, and she hoped that her eldest son William – who was barely a teenager at the time – would adopt some of his admirable qualities.
“I hope he grows up to be as smart about this as JFK Jr,” Diana told magazine editor Tina Brown – who interviewed the princess just weeks before her death – of William, according to her former aide Patrick Jephson.
“I want William to be able to handle things the way John does.”
Another reason she allegedly wanted to meet Kennedy – who had recently been named the sexiest man alive at the time – was to make her sister-in-law Sarah Ferguson jealous.
“The Princess’s desire to meet America’s most eligible bachelor was largely due to the fact that he was at that time an admirer of Fergie,” Jephson later wrote.
The late king is not the only celebrity the political wizard once attracted.
Just last month, Madonna named John F. Kennedy Jr. as her “best dk down” during her chat with playwright Jeremy O. Kennedy. Harris, Bob the Drag Queen, dancer Ivy Mugler, designer Raul Lopez, and ID’s Marcelo Gutierrez. The stars briefly dated in the 1980s.
One of Kennedy’s former close friends described the short-lived romance as “quite romantic” in the book “JFK Jr.: An Intimate Oral Biography” by Rosemary Terenzio and Liz MacNeil, released in 2024. “Nothing more than that. Hardly an adventure at that.”
Kennedy ended up with his wife, Carolyn Bessette Kennedy, whom he married in 1996. Their turbulent love story was recently captured on the silver screen in FX’s “Love Story,” which premiered in February.
Tragically, John and Caroline died in 1999 when John lost control of their small plane.