All About JFK Jr.'s Secret Meeting with Princess Diana and How They &x27;Stayed in Touch&x27; Caroline BlairSat, March 21, 2026 at 9:30 AM UTC 0 John F. Kennedy, Jr. ; Princess Diana.Credit: Mitchell Gerber/Corbis/VCG via Getty ;Â Pool Photograph/Corbis via Getty John F. Kennedy Jr. and Princess Diana secretly met at the Carlyle Hotel in New York City in December 1995 JFK Jr. pitched Diana to appear on the cover of George magazine, but she politely declined while saying that she'd consider it in the future Diana later wrote to JFK Jr.
All About JFK Jr.'s Secret Meeting with Princess Diana and How They 'Stayed in Touch'
Caroline BlairSat, March 21, 2026 at 9:30 AM UTC
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John F. Kennedy, Jr. ; Princess Diana.Credit: Mitchell Gerber/Corbis/VCG via Getty ;Â Pool Photograph/Corbis via Getty -
John F. Kennedy Jr. and Princess Diana secretly met at the Carlyle Hotel in New York City in December 1995
JFK Jr. pitched Diana to appear on the cover of George magazine, but she politely declined while saying that she'd consider it in the future
Diana later wrote to JFK Jr. expressing empathy over their shared struggles with the paparazzi and hoped to stay in touch
In the mid-1990s, John F. Kennedy Jr. and Princess Diana were two of the most famous people in the world.
After years of being on the other's radar, JFK Jr. and Diana secretly met at the Carlyle Hotel in New York City in December 1995. JFK Jr. asked to meet with the royal in hopes that she'd consider posing on the cover of his political lifestyle magazine, George.
Diana agreed to see him, and their personal assistants worked together to coordinate the meeting and ensure that it was kept private. While Diana politely turned down JFK Jr.'s cover proposal, she said she'd consider it in the future.
Diana later sent a letter to JFK Jr. in which she related to his experiences with intense media coverage and expressed hope that they could keep in touch. However, Diana tragically died on Aug. 31, 1997 — just a few months after she sent him that letter. Meanwhile, JFK Jr. and his wife, Carolyn Bessette, died in a plane crash less than two years later on July 16, 1999.
JFK Jr. and Bessette's romance has been dramatized in the FX series, Love Story: John F. Kennedy Jr. & Carolyn Bessette. In episode 8, titled "Exit Strategy," the couple learn about Diana's devastating death and react with both shock and fear.
Here's everything to know about John F. Kennedy Jr. and Princess Diana's secret meeting in 1995.
When did JFK Jr. and Princess Diana meet?
John F Kennedy Jr. speaks during a George magazine press conference on September 7, 1995 in New York ; Princess Diana.Credit: Ron Galella Collection via Getty ; Pool Photograph/Corbis via Getty
JFK Jr. and Princess Diana met on a weekday afternoon in December 1995 at her penthouse in the Carlyle Hotel in N.Y.C. Just one month before their meetup, Diana made headlines for her bombshell interview with the BBC in which she spoke about her divorce from King Charles.
Diana was in N.Y.C. to receive the Humanitarian of the Year award with the United Cerebral Palsy charity of New York, which took place on Dec. 11, 1995. JFK Jr. knew this, so he wrote a letter to her beforehand, and Diana decided it was the right time to meet him.
"Nobody wanted it to be public. It was never made public, so that made it quite fun, actually," Patrick Jephson, private secretary and equerry to Diana, said in PEOPLE's Liz McNeil and JFK Jr.'s assistant RoseMarie Terezino's book, JFK Jr: An Intimate Oral Biography. He added that she wanted to keep it "discreet," because "it had all the makings of a great gossip story."
"World's most eligible bachelor, wasn't he at the time?" he said. "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."
In order to ensure their privacy, Terenzio and Jephson worked together to create a plan for them to avoid paparazzi. They agreed that she'd go through the side door — where the paparazzi would be waiting for her — and JFK Jr. could sneak in through the front door without anyone noticing.
What happened during their secret meeting?
Princess Diana at the United Cerebral Palsy of New York dinner ; John F. Kennedy Jr. in New York City.Credit: Richard Corkery/NY Daily News Archive via Getty ; Mitchell Gerber/Corbis/VCG via Getty
Before they met in person, JFK Jr. prefaced his letter by saying that he wanted to ask her to be on the cover of George magazine dressed up as some sort of historical figure from America. Diana apparently went into the meeting knowing that she wasn't going to accept his offer, but she also wanted him to know that if he made the magazine a success, she'd consider doing a milestone issue.
Matt Berman, who was the creative director of George, sent him into the meeting with different versions of potential George covers and sketches — including ones with Diana getting bombarded by the paparazzi.
Of his pitch, Jephson recalled, "He showed her some mock-ups and she gave me a look and said, 'Well, you know, this is all very nice, John. Thank you. But I hope you'll forgive me if I don't take up the opportunity this time, but would love to maybe for your fiftieth or your hundredth issue or something.' "
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Both Diana and JFK Jr. recounted their meetup to their closest confidants. Jephson remembered Diana saying that the meeting "went well" and that "it was the right thing to do." She expressed a "degree of sympathy" about the media attention he'd received since he was a child.
Shared Jephson, "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."
Meanwhile, JFK Jr. told coworkers, that Diana was taller than he was expecting and that she had a "great pair of legs."
Did they ever talk again?
Diana, Princess Of Wales Attends The Victor Chang Research Institute Dinner in Sydney, Australia ; John F. Kennedy Jr. attends the Municipal Art Society Gala on October 5, 1998 in New York City.Credit: Julian Parker/UK Press via Getty ; Sonia Moskowitz/Getty
It's not clear if JFK Jr. or Diana ever met up again in person, but they "stayed in touch," per Terenzio. He continued to ask her for an interview for George, so she responded in a letter from Kensington Palace on Feb. 3, 1997.
Terenzio, who still has a copy of the letter, noted that Diana thanked him for his notes, but she once again declined to appear on the cover of George.
Diana also addressed the intense press attention they both received and wrote at the end of the letter, "'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!' " Terenzio shared in the oral biography.
Did Diana know Bessette?
Carolyn Bessette attends the final tribute to Gianni Versace in Milan, Italy ; Lady Diana, Princess of Wales, attends the last tribute to Gianni Versace in Milan, Italy.Credit: Alberto Pizzoli/Sygma via Getty (2)
In Love Story, Bessette's character, who is played by Sarah Pidgeon, claims that she was with Diana just a few weeks before her death at the funeral for Gianni Versace in July 1997.
However, it's not clear if Diana and Bessette ever spoke. Both women were among 2,000 attendees at Versace's funeral and were photographed leaving the church, but it's not known if they interacted.
Why did JFK Jr. not cover Diana's death in George?
John F. Kennedy Jr. at the Press Conference for George Magazine on September 7, 1995 in New York City.Credit: Ron Galella Collection via Getty
On Aug. 31, 1997, Diana and her boyfriend, Dodi Fayed, were killed in a car crash in Paris. The couple died after the car rammed into a column inside the Ponte de l'Alma tunnel as the driver attempted to dodge the paparazzi. A French investigation later found the driver solely responsible in the crash and alleged he was intoxicated at the time.
As a result of the shocking death, the editors at George wanted to find a way to cover Diana's life and death. However, JFK Jr. "didn't want to touch" it and was "mad" that they wanted to write about it, executive editor Elizabeth "Biz" Mitchell, said in McNeil and Terenzio's book.
The rest of the George editors had wanted to completely redo the issue, but JFK Jr. disagreed. At the time, he cited the fact that they were a monthly magazine, so it wasn't for breaking news.
On another level, though, JFK Jr. was hesitant, because he "felt it would become about him and the paparazzi," and people would ask him, "Are you and Carolyn afraid?"
JFK Jr.'s former professor turned friend and biographer, Steven M. Gillon, explained that JFK Jr. "had an emotional reaction" to her death, and even though "it was an important story to cover," he "hesitated."
As a compromise, his Creative Director Matt Berman created a photo essay to remember her legacy, entitled The Lady Vanishes.
on People
Source: "AOL Entertainment"
Source: Entertainment
Published: March 21, 2026 at 11:45AM on Source: RON MAG
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