In 1995, Princess Diana and John F. Kennedy Jr. were two of the most closely watched people on the planet, so arranging a secret meeting between the two was no easy feat.
But that’s exactly what their respective collaborators managed to orchestrate during a brief trip Diana made to New York City, the details of which have largely been kept secret. Until now.
The meeting was initially arranged at the behest of JFK Jr., who hoped to persuade the recently separated Diana to appear on the cover of his magazine, George. However, a new biography detailing the political heiress’s life has revealed that her real reasons for agreeing to the encounter may have been far less formal.
“It was never made public, so it was quite funny, actually,” recalls Diana’s private secretary, Patrick Jephson, in the pages of JFK Jr: An Intimate Oral Biography, written by RoseMarie Terenzio, a former executive assistant to Kennedy, and Liz McNeil.
‘Diana wanted it to be low-key because it had all the ingredients to be a great gossip story, didn’t it? The most eligible bachelor in the world… and she had just gotten married or was in the process of getting married. It would have been quite an intriguing dream.’
A new biography of JFK Jr. reveals the truth behind a secret meeting he had with Princess Diana in 1995
The political heir requested a meeting with Diana in New York City in the hope of persuading her to appear on the cover of his magazine, George, an offer she ultimately declined.
“She didn’t want that, but she was curious to meet him. Partly, I think, because Sarah Ferguson was crazy about him and Diana wanted, I think, to outdo her.”
RoseMarie, a former executive assistant to Kennedy and chief of staff to George, writes that Diana was scheduled to stay at the Carlyle Hotel and had arranged a meeting with the princess on a weekday afternoon to discuss possible coverage.
“There was a lot of concern,” he recalls. “Should he go in through the front door? Should he dress up? Because wouldn’t there be rumours that he was having an affair with her?… They were the two most famous people on the planet.”
In the end, he made it through the front door unnoticed, avoiding the paparazzi waiting for Diana at the side.
Jephson met Kennedy outside the hotel’s Bemelmans bar, in a “rather dark corridor”, and took him to the penthouse, where Diana was staying.
“He was smart. And she was smart,” he recalls. “It was a business meeting. They were dressed in formal clothes.”
However, Jephson says Kennedy seemed in awe of the beautiful woman sitting across from him, explaining that he “didn’t feel uncomfortable, but he certainly seemed to be on his best behavior.”
The encounter between the world’s most eligible bachelor and the princess had all the ingredients to be a major 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 and have remained in touch ever since.
“He sat on the edge of his chair and looked at her nervously,” she continues.
“She was very friendly, cheerful, you know, smiling and welcoming.”
He made his proposal for the cover and Diana respectfully declined, and ultimately Cindy Crawford was Kennedy’s cover star, but the two continued to talk until the allotted time was up.
“I can’t remember the words,” Jephson says, “but there was a certain degree of sympathy. I think she might have talked about the famous photograph of him as a child.”
“And she had a soft spot for him, having grown up with that name and being the object of public fascination. These were things she could relate to.
‘She didn’t see him the way the rest of the world saw him, as a big, famous, handsome guy. I think she saw him as someone who was rather vulnerable because he had grown up in the public eye.
“She saw in him another 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 reveals that Diana and JFK Jr. kept in touch and that he asked her for another interview two years later.
Diana’s former secretary Patrick Jephson believes Diana agreed to the meeting to “get over” Sarah Ferguson, who she knew was in love with JFK Jr.
She saw Kennedy as vulnerable because he had grown up in the public eye.
John Kennedy Jr. dancing with author RoseMarie Terenzio to Prince at George’s Christmas party in 1999
“On 3 February 1997, she wrote John a note from Kensington Palace. I still have a copy,” he writes.
“She said she “regretfully” had to decline his offer and that she would get back to him when the time was right. In the end, she wrote: “I hope” – and she stressed “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 deep irony of that first meeting at Carlyle: “I sent him a bunch of covers. He was drawing sketches with a magic marker on tracing paper.
‘I did one of her in a limo with paparazzi flashes: she was in the back with the windows half closed.
—How strange! Both of them were going to disappear in the next few years. Who would have guessed?
JFK Jr: An Intimate Oral Biography by RoseMarie Terenzio and Liz McNeil, published by Gallery Books