Home / PRINCESS DIANA / Princess Diana

Princess Diana's Ex-Secretary Reveals Bombshell Details About Her ‘Flirtatious’ Meeting With JFK Jr.

New details shed light on Princess Diana's secret meeting with JFK Jr., where the pair reportedly shared instant chemistry.

(L) Diana attends a state banquet in 1986; (R) John F. Kennedy Jr. at the Various Venues in Los Angeles (Cover Image Source: Getty Images | (R) Anwar Hussein; (L) Barry King)
(L) Diana attends a state banquet in 1986; (R) John F. Kennedy Jr. at the Various Venues in Los Angeles (Cover Image Source: Getty Images | (R) Anwar Hussein; (L) Barry King)

What happens when Britain’s "People’s Princess" meets America’s royalty? Decades later, Princess Diana's former private secretary is shedding new light on what really happened during the private meeting. Patrick Jephson opened up about what actually went down during her secret 1995 meeting with John F. Kennedy Jr. — revealing that the atmosphere was more than a little charged.

Princess of Wales arriving for a gala dinner in Chicago, Her dress is by designer Versace and her shoes by Jimmy Choo (Image Source: Getty Images | Tim Graham Photo Library)
Diana, Princess of Wales, arriving for a gala dinner in Chicago in a dress by designer Versace and matching shoes from Jimmy Choo. (Image Source: Getty Images | Tim Graham Photo Library)

The under-the-radar encounter took place in New York’s Carlyle Hotel, where Kennedy’s main agenda was to convince Diana to grace the cover of his new magazine, 'George'. The meeting was not supposed to attract attention. In fact, it was arranged so quietly that Jephson later described it as a "cloak-and-dagger" operation.

Jephson revealed to PEOPLE, “I sensed a vulnerability in him. When I met him, he was looking for reassurance, which is normal. He was respectful to her. She put him at his ease. They had a jolly social chat.” If JFK Jr. was looking forward to the meeting, Diana had her own reasons to be curious. By then, he was not just a member of America's most famous political family; he was also PEOPLE's Sexiest Man Alive and one of the country's most sought-after bachelors. “There was anticipation on both sides,” the former secretary added.

ohn F. Kennedy Junior at the opening of Hudson News today in Grand Central Station. (Image Source: Getty Images | Lawrence Schwartzwald)
John F. Kennedy Junior at the opening of Hudson News today in Grand Central Station. (Image Source: Getty Images | Lawrence Schwartzwald)

And yes, there was reportedly a little spark in the room. “It was a little bit flirtatious, as she would have been with any man. But because he was who he was, that gave it a slight extra sparkle,” Jephson described.

The meeting may have gone well, but it wasn't enough to win Diana over. Taking Jephson's advice, she politely turned down the cover offer, feeling the magazine was still too new to lend her star power to. However, she did leave the door open, suggesting she might reconsider if George made it to its 50th or 100th issue down the line.

The story between Diana and JFK Jr. did not end with that secret meeting. In fact, the Princess later reached out to Kennedy and his wife, Carolyn Bessette, after seeing the intense tabloid attention surrounding them.

John F. Kennedy Jr. (1960 - 1999) with his wife, Carolyn Bessette-Kennedy, USA, circa 1995. (Image Source: Getty Images | Rose Hartman)
John F. Kennedy Jr. (1960-1999) with his wife, Carolyn Bessette-Kennedy, USA, circa 1995. (Image Source: Getty Images | Rose Hartman)

In her book, The Kennedys and the Windsors: The Story of Two Dynasties, One Born, One Made, author Caroline Hallemann reveals that Princess Diana reached out to the couple in February 1997. Sympathizing with the intense media scrutiny they faced, Diana wrote, “I 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!” Tragically, Diana died in a car crash in Paris just months later, an event that intensified global scrutiny of paparazzi culture and media intrusion.

GET BREAKING ROYAL NEWS
STRAIGHT TO YOUR INBOX.

More Stories

40 years after Diana brought a whole room to a stop with a single dance, insiders say Kate has everything it takes to make repeat history.
By Abha Anindita · 1 DAY AGO
The couple’s hospital bedside moment and refugee camp visit revive memories of Diana’s direct and compassionate approach.
By Abha Anindita · FEB 27, 2026
Kristen Stewart revealed that she felt haunted by the late Princess, particularly while driving through Paris.
By Andrea Cutinho · FEB 6, 2026
The Duke said standing up to the press has come at a personal cost — but silence was no longer an option.
By Abha Anindita · JAN 22, 2026
George's public visibility grew significantly in the last year. While these ‘kinship’ lessons are important, they can be quite challenging at such a young age.
By Sakshi Singh · JAN 13, 2026
At 44, the Princess of Wales Is defining herself on her own terms, a royal expert has said.
By Abha Anindita · JAN 9, 2026
A former chef says the rest of the family followed the Queen’s menu, while Diana preferred a different food palette. But was there more to it than just healthy eating?
By Abha Anindita · JAN 8, 2026
Diana was reportedly viewed within Palace circles as significantly more effective than Charles at managing press attention following the breakdown of their marriage.
By Madhurima · DEC 29, 2025
Royal insiders and biographers explain why the holidays were a source of dread for the late princess.
By Abha Anindita · DEC 25, 2025
According to a source, Prince Harry and Meghan Markle are planning a film for 2027 to mark the 30th anniversary of Princess Diana's death.
By Andrea Cutinho · DEC 19, 2025