22-07-2025
The Truth Behind Princess Diana & JFK Jr.'s Secret Night Together After Her Divorce From Charles
If you think about the people who helmed the 90s together, two names come to mind: Princess Diana and JFK Jr. But did you know that the two had rumors swirling about their love life?
In 1996, JFK Jr. had an elaborate plan to convince Diana to be part of his George magazine by doing a secret meetup. 'We had to draw all these cover ideas up, and he took the drawings over to the Carlyle Hotel [in New York City] to meet her,' George magazine creative director Matt Berman told People.
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Diana was in the middle of her divorce from the then-Prince Charles and JFK Jr. was speculated to be an eligible bachelor after reportedly breaking up with his longtime girlfriend Carolyn Bessette. But what actually happened on that fateful night?
Did Princess Diana and JFK Jr. Date?
Princess Diana and JFK Jr. never dated, and the night they met at the hotel was purely planned for business purposes. The night did have a lot of hoops to get through since the paparazzi was overtly obsessed with the two of them at the time.
'I remember him saying, 'There's no way someone is not going to leak it. There's going to be paparazzi everywhere,'' RoseMarie Terenzio, John's executive assistant, recalled. 'Someone suggested he go in disguise and I said, 'That's ridiculous. You're not doing that!' '
Terenzio had been to the famed hotel before and observed that the paps wouldn't encounter them at the front door and advised him, 'Don't go in the side entrance, because if anyone does leak it beforehand, people will expect you to go in the side. So walk in the front door.' However, the press got word and they were caught red handed.
Diana politely rejected JFK Jr.'s offer to appear on George by writing him a note saying, 'Thank you so much, but not right now.''
'She didn't see him as the rest of the world saw him,' Diana's private secretary Patrick Jephson said. 'As this big, famous, handsome guy. She saw him, I think, as rather vulnerable because he had grown up in public.' However, her then-sister-in-law Sarah Ferguson did find John quite attractive, noting that she 'had the hots for him and Diana wanted to, I think, do one up on her.'
Terenzio also recalled of the impressions he got of her, 'I do remember him saying, 'She's really tall!' He also said she was very shy. He was surprised how demure she was. I think they had both met Mother Theresa so they spoke about that. And he said how lovely she was.' And Berman noted in his memoir JFK Jr., George, & Me 'The one funny thing he said was, 'She's got a great pair of legs.''
The two did exchange friendly to each other before their deaths. Terenzio recalled that Diana wrote a letter to them from Kensington Palace. 'I hope'—and she underlined the word '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!' Diana died shortly after she sent that letter after the paparazzi was chasing her in Paris. John and Carolyn—who he married in 1996— died in a plane crash in 1999.
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