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Sarah Ferguson Jealous of Princess Diana & JFK Jr Date

Story Center by Story Center
August 7, 2025
Reading Time: 8 mins read
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Sarah Ferguson Jealous of Princess Diana & JFK Jr Date

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These days, the stories we hear about the royal family involve King Charles’ feud with his youngest son, Prince Harry, or the state of Prince William and Kate Middleton’s marriage. But decades ago, Princess Diana and Sarah Ferguson, then the Duchess of York, were the center of conversations for their marriages to then Prince Charles and Prince Andrew, respectively, and also because of the relationship between them.

Now Andrew Lownie’s new book, Entitled: The Rise and Fall of the House of York, details, which serves a biography for both Prince Andrew and Sarah Ferguson, details how Fergie was “furious” after Princess Diana’s meeting with Jon F. Kennedy Jr. The meeting was concocted by JFR Jr. as part of an elaborate plan to convince Diana to be part of his George magazine.

Duchess Sophie, Princess diana

Related: Here’s what each royal inherited from Queen Elizabeth

“We had to draw all these cover ideas up, and he took the drawings over to the Carlyle Hotel [in New York City] to meet her,” George magazine creative director Matt Berman told People.

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Diana reportedly rejected the offer to appear in the magazine and wrote JFK Jr. a note that said, “Thank you so much, but not right now.” Princess Diana died in 1997 after a collision in Paris. JFK Jr., meanwhile, passed away in 1999 due to a plane crash.

“She didn’t see him as the rest of the world saw him,” Diana’s private secretary, Patrick Jephson, said in the book JFK JR: An Intimate Oral Biography. “As this big, famous, handsome guy. She saw him, I think, as rather vulnerable because he had grown up in public.” However, Sarah Ferguson, who was then Diana’s sister on law, “had the hots for him and Diana wanted to, I think, do one up on her.”

“It was never made public, so that made it quite fun, actually. Diana wanted it to be discreet because it had all the makings of a great gossip story, didn’t it? The world’s most eligible bachelor wasn’t he at the time? And she had just gotten unmarried or was in the process of getting unmarried. It would’ve been a rather intriguing thing to dream about. She didn’t want that, but she was curious to meet him.”

Sarah Ferguson Jealous of Princess Diana & JFK Jr Date

Entitled: The Rise and Fall of the House of York

Lownie’s book goes deeper into Sarah Ferguson’s “crush.” Reportedly, she once arranged a meeting with JFK Jr., and though he at first accepted, he later cancelled because his girlfriend at the time, Daryl Hannah, wasn’t pleased.

“‘That’s not going to bother me!’ ” Lownie quotes Fergie saying, “But it bothered Hannah, and Kennedy cancelled, claiming a prior engagement. Staff were then ordered to spy on his apartment all night to check that he had told the truth.”

According to the book, that wasn’t the end of it. “The duchess was not to be discouraged, especially after learning that Princess Diana had met Kennedy for 30 minutes at Christmas 1995 at a New York hotel. She was furious: ‘He’s mine! Why can’t she just leave him alone?’” the author writes. 

Furthermore, the Duchess of York reportedly nicknamed JFK. Jr. “Number Nine,” which was meant to indicate “his place in the order of her lovers.” The author even says she spent hours searching for articles about JFK Jr., cutting out photos of him in a swimsuit, and that she would even have conversations with her friends about what part of her personality he would like.

“A close confidante revealed: ‘She’ll suddenly ask, “Do you think Ken will mind that I don’t like such and such a thing?” It’s incredibly real to her, like a schoolgirl crush. She spends hours talking about him. The fact that she’s never even met him doesn’t seem to matter at all,’” Lownie wrote.

The book lists some of Sarah Ferguson’s other crushes, including Kevin Costner, Tiger Woods, and George Clooney.

‘ The preceding article may include information circulated by third parties ’

‘ Some details of this article were extracted from the following source stylecaster.com ’

Tags: Princess DianaSarah Ferguson
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