John F. Kennedy Jr. once proposed to Princess Diana at a private meeting at the Carlyle Hotel in December 1995, but the meeting was anything but romantic.
The late political heir contacted Princess Diana and asked her to appear on the cover of his new political lifestyle magazine, George.
“John had brought some ideas to the table for the cover shoot,” writes Caroline Haleman in her new book, The Kennedys and the Windsors, according to the Daily Mail.
“In one photo, she was seen wearing a tricorn hat similar to that from the Revolutionary War, and in another photo, she was sitting in the back seat of a limousine with the windows half-closed, oddly enough to avoid photographers.”
Unfortunately for Kennedy, the princess, who tragically died in a car accident the following year, had already decided that she had no interest in being published in the magazine before hearing Kennedy’s idea.
“She needed the magazine to be successful before she could appear on its cover in public,” Halleman writes. “Even with Kennedy in control of publishing, it was not a guaranteed prospect.”
Mr. Halleman alleges that Princess Diana told Mr. Kennedy: thank you. However, I hope you’ll forgive me for not taking up the opportunity this time, but I’d love to be a part of it, maybe issue 50 or 100 or something. ”
When Kennedy returned to George’s office, he reportedly told employees that the Princess Diana job had been closed, but admitted he was still curious about the Princess Diana feature.
“Well, she said no,” Kennedy told them. “But she had great legs.”
One theory as to why she still chose to meet with Kennedy is that she greatly admired the way he conducted himself in public and hoped that her eldest son William, then just a teenager, would inherit some of his admirable qualities.
“I hope he grows up to be as smart as John Kennedy Jr.,” Princess Diana told magazine editor Tina Brown, who interviewed the princess in the weeks before her death, about Prince William, according to her former assistant Patrick Jephson.
“I want William to be able to handle things as well as John.”
Another reason she wanted to meet Kennedy, who had just been named 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 owed in no small part to the fact that he was Fergie’s special pin-up at the time,” Jephson later wrote.
The late royal family is not the only celebrity to have been courted by a politician.
Just last month, Madonna named JFK Jr. her “best down” in a conversation with playwright Jeremy O. Harris, drag queen Bob, dancer Ivy Mugler, designer Raul López and ID’s Marcello Gutierrez. The stars briefly date back to the 1980s.
One of Kennedy’s former close friends, in Rosemary Terenzio and Liz McNeil’s JFK Jr.: An Intimate Oral Biography, published in 2024, described the fleeting romance as “a total fling,” adding, “It was nothing more than that. It was just a fling.”
Kennedy famously eventually married his wife Carolyn Bessette Kennedy, whom he married in 1996. Their tumultuous love story was most recently brought to the silver screen in FX’s “Love Story,” which premiered in February.
Sadly, John and Carolyn died in 1999 when John lost control of his small plane.
