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Live the Gossip > Royal Family > New details of Princess Diana and JFK Jr.’s ‘flirtatious’ meeting exposed 30 years later
Royal Family

New details of Princess Diana and JFK Jr.’s ‘flirtatious’ meeting exposed 30 years later

Written by: News Room Last updated: June 10, 2026
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New details have emerged surrounding Princess Diana and John F. Kennedy Jr. private meeting in 1995 at New York’s Carlyle hotel.

It was there that the attorney tried to convince the royal to grace the cover of his new magazine, George.

“She was quick-witted and fun to be with,” Diana’s private secretary, Patrick Jephson, recalled to People in an interview published Wednesday. “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.”

He added that there “was anticipation” from both the princess and Kennedy — who had been recently named the Sexiest Man Alive a few years prior — when the pair had coffee in her suite.

“It was a little bit cloak and dagger,” Jephson continued.

Despite declining Kennedy’s offer to appear on the magazine, the princess said she would consider being in the 50th or 100th issue of George.

“I sensed a vulnerability in him,” Jephson explained about the attorney’s demeanor. “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.”

“They parted on warm terms,” he noted.

Jephson, meanwhile, gave two reasons why he believes the princess took the meeting with Kennedy.

One theory being that Diana admired the businessman — even wanting her son William to carry himself as Kennedy did in the public eye.

“I’m hoping he’ll grow up to be as smart about it as John Kennedy Jr.,” she told magazine editor Tina Brown about her eldest child, according to Jephson. “I want William to be able to handle things as well as John does.”

Allegedly, Diana was also looking to make sister-in-law Sarah Ferguson jealous.

“The princess’s wish to meet America’s most eligible bachelor owed more than a bit to the fact that he was at the time a particular pin-up of Fergie’s,” Jephson penned.

Earlier this week, Caroline Hallemann opened up about Diana and Kennedy’s secret meeting in her new book, “The Kennedys and the Windsors,” per the Daily Mail.

“John had brought along with him several ideas for the cover shoot,” she writes.

“One featured her wearing a three-corner hat like one from the Revolutionary War, another, oddly enough, showed her in the back of a limousine with the window rolled halfway up, in an attempt to avoid photographers.”

Hallemann also shared why Diana turned down the prospect.

She pens that the mom of two “needed the magazine to be a success before she’d publicly front it.”

“Even with a Kennedy at the helm of the publication, that was hardly a guaranteed prospect,” the author continues.

However, it was no hard feelings on Kennedy’s end.

The writer alleges that when he got back to the office, he told his staff, “Well, she said no. But she had a great pair of legs.”

George magazine debuted in 1995 and published its last issue in 2001.

At the time of their meeting, Diana was married to Prince Charles, with whom she wed in 1981. The couple welcomed Prince William and Prince Harry before divorcing in 1996.

Just one year later, in 1997, the princess died in a high-speed car crash in Paris.

For his part, the former president’s son was dating Carolyn Bessette in 1995, before the pair tied the knot in 1996.

The two had a famously volatile relationship until their tragic deaths in 1999, which was explored on FX’s “Love Story” earlier this year.

The plane Kennedy was piloting crashed into the ocean off the coast of Martha’s Vineyard, Massachusetts, that July, with Bessette and her sister, Lauren, on board.

Read the full article here

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