When JFK Jr. and Princess Diana met in the summer of 1995, they were two of the most famous people on the planet.
At the time, John was trying to convince Diana to pose for the cover of his political magazine George.
“We had to draw all these cover ideas up, and he took the drawings over to the Carlyle Hotel to meet her,” said Matt Berman, George magazine creative director who made the sketches.
The meeting took place in Diana’s suite and lasted for an hour and a half.
“He wanted to do a respectful piece,” RoseMarie Terenzio, John’s executive assistant recalls. She accompanied him that day to the hotel and the two were able to avoid the press simply by walking in the front door of the esteemed hotel.
“All the press was on the side door!” recalls Terenzio with a laugh.
The meeting did not go in John’s favor Terenzio said, “She wrote John a note that said, ‘Thank you so much, but not right now.’”
JFK Jr. did tell his George colleagues after their meeting. “He was very careful what he said,” recalls Berman. “The one funny thing he said was, ‘She’s got a great pair of legs.’ “
After meeting with the famous Princess, Terenzio said JFK remarked ““I do remember him saying, ‘She’s really tall!’ He also said she was very shy. He was surprised how demure she was. I think they had both met Mother Theresa so they spoke about that. And he said how lovely she was.”
In 1995 when the pair met in New York, 33 year-old Diana had been separated from Charles for 3 years. Kennedy, who was 34 years-old at the time, had a string of high profile romances with celebrities including actress Daryl Hanna and Marilyn Munro, as well as allegedly had a one-night stand with the princess in the room that overlooked Central Park.
Simone Simmons, Princess Diana’s energy healer, was a frequent visitor to Kensington Palace.
Simmons claims that Diana told her that she was ‘bowled over’ by John’s charm and good looks.
“We started talking, one thing led to another – and we ended up in bed. It was pure chemistry,” Simmons said.
Stunned by the news Simmons told the Sun newspaper of her reaction. “My mouth dropped open. I cried out: ‘What! You’re joking, aren’t you?’ and I really thought she was. She replied: ‘No, I’m not. It happened. And he was an amazing lover – a ten, the tops’.”
While the pair allegedly stayed in touch, Diana realized that she wasn’t going to be joining “America’s Royal Family”. The following year Kennedy married Carolyn Bessette, a PR advisor for Calvin Klein.
Diana kept her relationships out of the public eye until finding love with Dodi Fayed, the millionaire whom she died in a car crash with in Paris in 1997.
Kennedy died in a plane crash 2 years later with his wife Carolyn and her sister Lauren Bessette.
Not everyone believed the story, however. Diana’s former butler Paul Burrell told the Mirror, “Simone has concocted a fantastical story of nonsense in much the same vein as the mystical rubbish she used to feed the princess. That Diana had an affair with JFK Jr is simply untrue.”
He added that their meeting was simply to discuss the magazine and nothing more.