Inside Princess Diana and JFK Jr.'s secret meeting that fueled romance rumors for decades
Caroline Hallemann's 'The Kennedys & the Windsors' details how Kennedy quietly stayed in touch
{{#rendered}} {{/rendered}}In December 1995, the world's two most famous people met in secret at New York City's Carlyle Hotel.
John F. Kennedy Jr. hoped to persuade Princess Diana to grace the cover of his magazine, "George." The Princess of Wales, for her part, wanted to meet the man who had managed the impossible: living under an unforgiving media spotlight without being consumed by it.
Caroline Hallemann wrote about the encounter in her book, "The Kennedys & the Windsors," which explores the two dynasties and how their paths crossed over the years.
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In December 1995, Princess Diana and John F. Kennedy Jr. held a private meeting at New York City's Carlyle Hotel. (Tim Graham Photo Library via Getty Images; Barry King/WireImage/Getty Images)
"It was this clandestine meeting, and they were able to keep it a secret," Hallemann told Fox News Digital. "They were both hounded by paparazzi throughout their lives. That's something they had to deal with, but they were able to maintain privacy around this moment."
"I spoke with Patrick Jephson, who was Princess Diana's private secretary at the time, and I spoke with Rosemarie Terenzio, who was JFK Jr.'s executive assistant at ‘George’ magazine, to hear about what happened in this meeting," she shared. "Patrick was actually in the room when they met."
{{#rendered}} {{/rendered}}John F. Kennedy Jr. was the co-founder and editor-in-chief of "George" magazine, which launched in September 1995. (Ron Galella/Ron Galella Collection via Getty Images)
Hallemann wrote that while Kennedy was "excited" to meet the royal, he was also "annoyed about everybody hinting that this would be a marriage made in heaven if they could be together."
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At the time, Kennedy was considered the world's most eligible bachelor. But for Diana, who had officially divorced then-Prince Charles, the meeting was purely professional.
{{#rendered}} {{/rendered}}"Patrick shared that this was really a business meeting," said Hallemann. "[Kennedy] thought that she quintessentially represented what the magazine was trying to achieve, which was to focus on the intersection of popular culture, politics and celebrity. And Princess Diana, from the start of the meeting, knew that she was going to say no, but she still wanted to meet with him anyway, which I think is quite telling."
"The Kennedys & the Windsors: The Story of Two Dynasties, One Born, One Made" by Caroline Hallemann is available now. (G.P. Putnam's Sons)
Kennedy and Diana had met before, the book revealed. About a decade earlier, they both attended a luncheon in Virginia during the 1985 royal visit to Washington, D.C.
In this undated photo, John F. Kennedy Jr. is seen addressing the Democratic National Convention in Washington, D.C. (Getty Images)
"She has the most unusual upward glance, really seductive," Kennedy told his friend Billy Noonan, adding that she had "the most unusual blue eyes," Hallemann wrote.
{{#rendered}} {{/rendered}}As for Diana, she was "keen" on the idea of spending time with Kennedy away from cameras.
Princess Diana passed away on Aug. 31, 1997. She was 36. (Tim Graham Photo Library/Getty Images)
"[His mother] Jackie Kennedy was a role model for Princess Diana in terms of how Jackie was able to raise her children in the public eye," Hallemann explained. "And I think that Princess Diana wanted to meet with John Jr. just to see how he managed life in the public eye."
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{{#rendered}} {{/rendered}}In this undated photo, first lady Jacqueline Kennedy is seen leaving The Carlyle to visit her father-in-law, Joseph P. Kennedy, at the hospital before returning to Washington. She spent three days there. (Getty Images)
At first, it was suggested that Kennedy would wear a disguise to throw off the paparazzi. But Kennedy told friends, "I'm not going anywhere in disguise; that's the stupidest thing ever."
The hotel's discretion was described as "extraordinary," Hallemann wrote. Kennedy had lived there following his father's assassination, and it was also a favorite of Diana's whenever she was in New York.
When Kennedy came face to face with the princess, he appeared "nervous."
{{#rendered}} {{/rendered}}John F. Kennedy Jr. and Rosemarie Terenzio attend a New York Knicks versus Chicago Bulls game at Madison Square Garden in New York City. (Linda Cataffo/NY Daily News)
"He was quite in awe of her," Jephson told Hallemann. "Not uncomfortable, but he certainly seemed to be on his best behavior." Diana was "very cool — and jolly, you know, and smiley and welcoming."
Princess Diana wears a red two-piece suit by Catherine Walker during a visit to London Lighthouse, a center for people affected by HIV and AIDS, in London, England, on Oct. 8, 1996. (Princess Diana Archive/Getty Images)
Hallemann told Fox News Digital the pair "spoke about a number of things," including Mother Teresa and the paparazzi.
"But ultimately, for John, the goal of this meeting was for Diana to be featured in ‘George’ magazine," she said. "Sadly, he walked away disappointed in that regard."
{{#rendered}} {{/rendered}}Prince Charles and Princess Diana's divorce was finalized on Aug. 28, 1996. (Tim Graham Photo Library/Getty Images)
After giving Jephson "a sly glance," Diana told Kennedy that she would perhaps consider appearing in the 50th or 100th issue. Her decision was final. Still, the two spent "an hour or so together" talking.
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Princess Diana is seen with her private secretary Patrick Jephson. (Tim Graham Photo Library/Getty Images)
Later, rumors claimed Kennedy and Diana had an affair that was consummated at the Carlyle that day in a "moment of pure lust." Jephson told Hallemann he was in the room the entire time.
{{#rendered}} {{/rendered}}"I stayed in the room throughout and was not aware of any mad, passionate activities," he said. "My observation was that it was a kind of mutual sounding out. It was a kind of appraisal, and it wasn't overtly flirtatious, but it was friendly."
Princess Diana was born on July 1, 1961. (Julian Parker/UK Press)
While Kennedy didn't get the answer he was hoping for, Diana left a lasting impression.
Princess Diana leaves the first anti-AIDS bookshop in Paris on Nov. 14, 1992. (Vincent Amalvy/AFP)
"I think he was charmed by her," said Hallemann. "He thought she was quite beautiful. There's one quote that's repeated by several people who spoke to him about her. [He] said she had great legs. I think he thought she was attractive."
{{#rendered}} {{/rendered}}"But it was really a business meeting — for him it was," said Hallemann. "It wasn't a social call, and he was really hopeful and saw the value she might bring by appearing in the magazine, and that element didn't work out."
Princess Diana reportedly didn't completely rule out the idea of posing for "George" magazine someday. (Anwar Hussein/Getty Images)
According to the book, Diana wrote Kennedy a note. It read, "Thank you so much, but not right now." Again, she agreed to appear on a future cover.
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{{#rendered}} {{/rendered}}Princess Diana talks to an officer after watching an air display at RAF Wittering in Lincolnshire in September 1995. Princess Diana's private secretary Patrick Jephson is on the right. (Pool/Getty Images)
Kennedy never gave up on the idea. The book describes how he quietly stayed in touch with Diana, asking her for an interview more than once.
In February 1997, she wrote him a letter saying she had to "regrettably" turn down his offer once more. She wrote, "'I hope"—with "hope" underlined—'"that the media are leaving both of you and [your wife] Carolyn alone. I know how difficult it is, but believe it or not, the worst paparazzi are here in Europe!"
John F. Kennedy Jr. married Carolyn Bessette on Sept. 21, 1996. (Ron Galella/Ron Galella Collection via Getty Images)
On Aug. 31, 1997, Diana died from injuries sustained in a Paris car crash. She was 36. At the time, she was riding in a car that was being pursued by paparazzi.
{{#rendered}} {{/rendered}}A multicolored sea of floral tributes lies outside the gates of Princess Diana's London home after news of her death in a Paris car crash reached Britain. (Liba Taylor/Corbis)
"Princess Diana's death affected JFK Jr.," said Hallemann. "He saw a real similarity between them. He saw how much media interest and scrutiny there was, and he saw the role the media had played in her death. It worried him."
"In particular, it worried him because of the way his wife reacted to it," Hallemann continued. "Carolyn was deeply upset by Princess Diana's death. She was deeply rattled by her own experience with the paparazzi and also by the way Princess Diana died. She was already struggling with her relationship with the media, and this only took it one step further."
In her lifetime, Carolyn Bessette Kennedy struggled with the media scrutiny. (Andrew Savulich/NY Daily News Archive via Getty Images)
Kennedy and his wife, Carolyn Bessette Kennedy, died in a plane crash less than two years later, on July 16, 1999.
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John F. Kennedy Jr. and Carolyn Bessette Kennedy attend an exhibition at the Whitney Museum in New York City on Nov. 4, 1996. (Sonia Moskowitz/Getty Images)
"I think that when people die young, they are mythologized in a way, and they are canonized in a way," said Hallemann. "For both Princess Diana and JFK Jr., these were two people who lived under enormous media scrutiny. They did a great deal of good, but they were also just people. And for one moment, they came together away from the spotlight."