Princess Diana and JFK Jr. Once Had a Secret ‘Flirtatious’ Encounter

Princess Diana and JFK Jr. shared a secret, one-time encounter in December 1995 — and the man who witnessed it is now sharing what really happened.

Two of the most famous people in the world were once in the same room together in December 1995. It would be the first — and only — time they ever met.

Those two people were Princess Diana and John F. Kennedy Jr. The meeting was private and deliberately kept under wraps, with John slipping through the back entrance of New York's Carlyle Hotel to meet the late royal.

John, then 34, was hoping to persuade Diana to appear on the cover of his new magazine, "George." After an initial greeting in a quiet corner of the lobby, Diana's private secretary Patrick Jephson escorted him up to the princess's suite, where the two sat down for coffee and conversation.

"It was a little bit cloak and dagger," Patrick told PEOPLE in a recent interview. He had advised Diana that appearing in the magazine would amount to giving the fledgling publication "a seal of approval it didn't yet merit."

Diana politely declined — though she did suggest she might consider appearing in a future issue, perhaps the 50th or 100th. Even so, the brief encounter left a lasting impression on Patrick.

"I sensed a vulnerability in him," he recalled. "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."

By that point, John had long since built his own considerable celebrity. But even he wasn't immune to Diana's magnetism. "I spent eight years seeing people who might consider themselves important and famous become like jellies when presented to the princess," Patrick said.

Diana, for her part, was equally aware of who she was dealing with. Named PEOPLE's Sexiest Man Alive in 1988, John was one of America's most eligible and talked-about bachelors. "There was anticipation on both sides," Patrick noted.

"She was quick-witted and fun to be with," he continued. "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."

By the time the meeting wrapped up, two of the defining figures of their era had shared a rare, unguarded moment away from the public eye. "They parted on warm terms," Patrick said.

"George," which John co-owned with Michael J. Berman, went on to feature a roster of major names — among them Cindy Crawford, Robert De Niro, Demi Moore, Drew Barrymore, and Barbra Streisand.

But by 1997, the lifestyle and politics outlet was under strain, beset by creative and financial tensions. John and Berman clashed repeatedly, with disputes that on at least one occasion turned physical. Berman departed the magazine later that year.

Tragedy struck in 1999 when John and his wife, Carolyn Bessette-Kennedy, died in a plane crash into the Atlantic Ocean near Martha's Vineyard. With its founder gone, "George" saw a swift decline in both readership and advertising revenue, and the publication folded in January 2001.