Princess Diana's 'flirtatious' private meeting with John F. Kennedy Jr detailed by former aide

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GB NEWS

Ben McCaffrey

By Ben McCaffrey


Published: 10/06/2026

- 14:25

Updated: 10/06/2026

- 14:27

The pair met at a New York hotel in December 1995

Princess Diana and John F Kennedy Jr shared a "flirtatious" private meeting in New York, it has been claimed.

December 1995 saw two of the world's most recognisable figures come together for their first, and only, encounter.


JFK Jr, then 35, had entered New York's Carlyle hotel through a rear entrance, determined to avoid detection, while Diana awaited his proposition.

The son of the assassinated President was looking to secure the 34-year-old princess for the cover of his fledgling political magazine, George.

Known for its classic covers and iconic tagline "Not Just Politics As Usual," George quickly rose to prominence in the 90s.

So, after the pair met in a quiet corner of the hotel's lobby, JFK Jr was swiftly escorted to the princess's suite by Diana's former private secretary Patrick Jephson, where the pair shared a coffee - and many interests.

Speaking to People, Mr Jephson detailed the "flirtatious" and "warm" meeting the pair shared, as they discussed Diana's appearance in the magazine.

"It was a little bit cloak and dagger," Mr Jephson recalls of the secretive meeting.

\u200bPrincess Diana

Princess Diana and John F Kennedy Jr shared a 'flirtatious' private meeting in New York, it has been claimed

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GETTY

"I sensed a vulnerability in him. 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."

Mr Jephson had urged Diana against granting the cover appearance, advising that it would bestow "a seal of approval it didn't yet merit" upon the publication.

George was founded by JFK Jr and Michael J Berman in 1995.

John F Kennedy Jr

John F Kennedy Jr co-founded the George magazine in 1995

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GETTY

The late Princess of Wales graciously declined the offer, though she floated the possibility of featuring on a future milestone issue.

According to Caroline Hallemann, author of The Kennedys & the Windsors, Diana 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 50th or your 100th issue or something.”

"There was anticipation on both sides," Mr Jephson added. "She was quick-witted and fun to be with.

"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.

"They parted on warm terms."

Their brief 1995 encounter would prove to be their only, as both icons of the decade had tragically died before the turn of the millennium.