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Inside Princess Diana and JFK Jr.’s secret meeting that fueled romance rumors for decades

Last updated: July 16, 2026 12:32 pm
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Inside Princess Diana and JFK Jr.'s secret meeting that fueled romance rumors for decades
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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.

“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.”

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.”

WATCH: JKF JR.’S SECRET MEETING WITH PRINCESS DIANA REVEALED

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.

“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 , 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.”

Kennedy and Diana had met before, the book revealed. About a decade earlier, they both attended a luncheon in Virginia during to Washington, D.C.

“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.

As for Diana, she was “keen” on the idea of spending time with Kennedy away from cameras.

“[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.”

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 .

When Kennedy came face to face with the princess, he appeared “nervous.”

“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.”

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.”

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.

Later, rum

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