In 1995, Princess Diana and John F. Kennedy Jr. were among the most closely watched people on the planet, so arranging a secret meeting between the two was no easy task.
But that’s exactly what their respective staffs managed to orchestrate during a short trip Diana took to New York City, the details of which have been kept largely secret. Until now.
The meeting was initially arranged at the request of JFK Jr., who hoped to persuade the recently divorced Diana to appear on the cover of his magazine George. However, a new biography chronicling the political scion’s life has now revealed that her real reasons for agreeing to the meeting may have been far less formal.
“It was never made public, so that was kind of fun,” Diana’s private secretary, Patrick Jephson, recalled in the pages of JFK Jr: An Intimate Oral Biography, written by RoseMarie Terenzio, Kennedy’s former executive assistant, and Liz McNeil.
‘Diana wanted it to be discreet, because it had all the makings of a great gossip story, didn’t it? The most eligible bachelor in the world… and she was newly single or in the process of becoming single. It would have been quite an intriguing thing to dream about.
A new biography of JFK Jr. reveals the truth behind a secret meeting he had with Princess Diana in 1995
The political scion requested a meeting with Diana in New York City in hopes of persuading her to appear on the cover of his magazine George, an offer she ultimately declined.
“She didn’t want to, but she was curious to meet him. Partly, I think, because Sarah Ferguson had a crush on him and Diana, I think, wanted to seduce her.”
RoseMarie, Kennedy’s former executive assistant and chief of staff to George, writes that Diana was to stay at the Carlyle Hotel and that she had arranged a meeting with the princess on a weekday afternoon to discuss the possible cover-up.
“There was so much anxiety,” she recalled. “Should he come in through the front door? Should he change his clothes: because aren’t there rumors that he’s having an affair with her? … They were the two most famous people on the planet.”
Finally, he walked in through the front door unnoticed, without being noticed, thus avoiding the paparazzi who were waiting for Diana outside.
Jephson met Kennedy outside the hotel’s Bemelmans Bar in a ‘fairly dark corridor’ and took him to the penthouse where Diana was staying.
“He was smart. And she was smart,” he recalls. “It was a work meeting. Business attire.”
However, Jephson says Kennedy seemed impressed by the beautiful woman sitting across from him. He said he “didn’t feel uncomfortable, but certainly behaved very well.”
The meeting between the world’s most eligible bachelor and the princess had all the makings of a great gossip story – and the couple’s staff did everything they could to keep it under wraps
The couple met in Diana’s penthouse suite at the Carlyle Hotel – and stayed in touch afterward
“He was actually sitting on the edge of his seat, looking at her nervously,” he continues.
“She was very cool — and cheerful, you know, and happy and welcoming.”
He made a proposal for the cover, but Diana politely declined. In the end, Cindy Crawford became Kennedy’s cover star. However, the two continued to talk until the agreed time was up.
“I can’t remember the words,” says Jephson, “but there was a certain amount of sympathy. I think she was referring to the famous photo of him as a little boy.
‘And she had sympathy for him, because he grew up with that name and was the object of public fascination. These were things she could identify with.
“She didn’t see him the way the rest of the world saw him. As this big, famous, handsome guy. She saw him, I think, as quite vulnerable because he had grown up in the public eye.
“She saw in him a fellow victim… of life in the public eye and the difficulty of knowing who to trust. And I think that created a connection between them.”
Terenzio says that Diana and JFK Jr. kept in touch and that he invited her back for an interview two years later.
Diana’s former secretary Patrick Jephson believes Diana agreed to the meeting to outdo Sarah Ferguson, who she knew had a crush on JFK Jr.
She saw Kennedy as vulnerable because he had grown up in the public eye
John Kennedy Jr. dances with author, RoseMarie Terenzio, at Prince during George’s Christmas party in 1999
‘On February 3, 1997, she wrote John a note from Kensington Palace. I still have a copy of it,’ she writes
‘She said that she ‘sadly’ had to decline his offer and that she would contact you again when the time was right. At the end she wrote: ‘I hope’ – and she underlined ‘hope’ – ‘that the media will leave you and Carolyn alone. I know how hard it is, but believe it or not, the worst paparazzi are here in Europe.’
Matt Berman, George’s creative director, reflected on the profound irony of that first meeting at the Carlyle: ‘I sent him a stack of covers. I drew sketches – Magic Marker on tracing paper.
‘I shot one where she was in a limo with paparazzi flashes, she was in the back with the windows halfway down.
“How weird is that? They’re both going to be gone in the next few years. Who would have called that?”
JFK Jr: An Intimate Oral Biography by RoseMarie Terenzio and Liz McNeil, published by Gallery Books