‘It was a little bit flirtatious’

Princess Diana and JFK Jr. are some of the most emblematic figures of the ’90s. According to Diana’s private secretary, the two met once in their lives, with the meeting having a special and flirtatious edge to it. 

Patrick Jephson, Princess Diana’s private secretary, discussed the secret meeting in an interview with PEOPLE. “She was quick-witted and fun to be with,” he said. “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.”

According to Jephson, the meeting was done with JFK Jr, hoping to feature Diana on the cover of George Magazine, a publication exploring politics and pop culture. The two reportedly met in the quiet corner of a lobby, with Jephson describing it as “cloak and dagger.” 

© Rick Maiman

While there was “anticipation on both sides,” Diana politely declined, saying that she might consider appearing on George’s 50th or 100th issue. 

The two parted on good terms. “I sensed a vulnerability in him,” said Jephson. “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.”

The meeting took place in 1995, when JFK Jr had been named PEOPLE’s Sexiest Man Alive, and Diana was at the top of her fame, becoming a global icon. He launched George magazine that same year, with it publishing its last issue in 2001.

JFK Jr’s pitch for Diana

© Princess Diana Archive

Caroline Hallerman discussed JFK Jr and Diana’s meeting in her book, “The Kennedys and the Windsors,” according to the Daily Mail. “John had brought along with him several ideas for the cover shoot,” reads the book.

“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.”

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

According to Hallerman, JFK Jr didn’t take the loss too seriously. “Well, she said no. But she had a great pair of legs,” JFK Jr allegedly told his staff. 

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