In 1995, Princess Diana and John F. Kennedy Jr. were two of the most closely-watched people on the planet – so organizing a secret meeting between the two of them was no easy feat.
But that is exactly what their respective staffers managed to orchestrate during a brief trip that Diana made to New York City, the details of which have been kept largely under wraps. Until now.
The meeting was initially arranged at the behest of JFK Jr. who had hoped to convince the newly-separated Diana to appear on the cover of his magazine, George. However a new biography detailing the life of the political scion has now revealed that her real reasons for agreeing to the meet-up may have been far less formal.
‘It was never made public so that made it quite fun, actually,’ Diana’s private secretary, Patrick Jephson, recalls 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? World’s most eligible bachelor… and she had just got unmarried or was in the process of getting unmarried. It would’ve been a rather intriguing thing to dream about.
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The political scion requested a meeting with Diana in New York City in the hopes of persuading her to appear on the cover of his magazine, George, an offer she ultimately turned down
‘She didn’t want that, but she was curious to meet him. Partly, I think, because Sarah Ferguson had the hots for him and Diana wanted to, I think, do one up on her.’
RoseMarie, Kennedy’s former executive assistant and chief of staff at George, writes that Diana was due to be staying at the Carlyle hotel, and she’d arranged for a meeting with the princess on a weekday afternoon to discuss the potential cover.
‘There was all this worry,’ she recalls. ‘Should he go in the front door? Should he wear a disguise: because won’t there be rumors that he’s having an affair with her? … They were the two most famous people on the planet.’
In the end, he walked right through the front door without being noticed, avoiding the paparazzi who were waiting around the side for Diana.
Jephson met Kennedy outside the hotel’s Bemelmans Bar in a ‘rather dark passageway’ and took him up to the penthouse, where Diana was staying.
‘He was smart. And she was smart,’ he recalls. ‘It was a working meeting. Business attire.’
However, Jephson says Kennedy seemed in awe of the beautiful woman sitting opposite him, explaining that he was ‘not uncomfortable but he certainly seemed to be on his best behavior.
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The meeting between the world’s most eligible bachelor and the princess had all the makings of a great gossip story – and the pair’s staff went to great lengths to keep it hidden
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The pair met in Diana’s penthouse suite at the Carlyle – and stayed in touch afterwards
‘He rather sat on the edge of his chair and looked nervously at her,’ he continues.
‘She was very cool – and jolly, you know, and smiley and welcoming.’
He made his pitch for the cover and Diana respectfully declined, with Cindy Crawford ultimately going on to serve as Kennedy’s cover star, but the pair continued talking until their allotted time was over.
‘I can’t remember the words,’ says Jephson, ‘but there was a degree of sympathy. I think she might have spoken about the famous picture of him as a little boy.
‘And she had sympathy for him growing up with the name and being the object of public fascination. These were things that she could relate to.
‘She didn’t see him as the rest of the world saw him. As this big, famous, handsome guy. She saw him, I think, as rather vulnerable because he had grown up in public.
‘She saw in him a fellow victim… of life in the public eye and difficulty knowing who to trust. And I think that that did create a connection between them.’
Terenzio reveals that Diana and JFK Jr stayed in touch, and he asked her again for an interview two years later.
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Diana’s former secretary Patrick Jephson believes that Diana agreed to the meeting in order to ‘one up’ Sarah Ferguson whom she knew had a crush on JFK Jr.
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She saw Kennedy as vulnerable because he had grown up in the public eye
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John Kennedy Jr dancing with the author, RoseMarie Terenzio, to Prince at 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 “regrettably” she must decline his offer and that she would get back in touch when the time was right. At the end, she wrote: “I hope” – and she underlined “hope” – ‘the media are leaving both you and Carolyn alone. I know how difficult it is, but believe it or not, the worst paparazzi are here in Europe.’
Matt Berman, the creative director of George, reflected on the deep irony of that first meeting at the Carlyle: ‘I sent him over with a bunch of covers. I would draw sketches – Magic Marker on tracing paper.
‘I did one of her in a limousine with paparazzi flash bulbs – it was her in the back with the windows half up.
‘How weird is that? They were both not gonna be around in the next few years. Who would’ve called that one?’
