John F. Kennedy Jr's Fondness For a Particular Body Part of Princess Diana Revealed — As Its Claimed Late Royal Met Up with Hunk to Make Sister-in-Law Sarah Ferguson 'Jealous'
John F. Kennedy Jr. was a big admirer of Princess Diana, especially a certain feature of the late royal.
June 8 2026, Published 2:20 p.m. ET
John F. Kennedy Jr was a big admirer of the late Princess Diana – especially her legs, RadarOnline.com can reveal.
The late politician is said to have propositioned Diana at a private meeting held at the Carlyle Hotel in December 1995.
'She Has a Great Pair of Legs'
JFK Jr. told staffers working for his magazine about Princess Diana's 'great legs.'
He hoped to secure the glamorous royal as the cover star of his new political lifestyle magazine, George.
After she rejected his proposal, he returned to the George offices and allegedly told employees not only about Diana's shutdown, but how enamored he was by a particular feature of the princess.
According to author Caroline Hallemann in her new book, The Kennedys and the Windsors, JFK Jr. told staffers: "Well, she said no. But she had a great pair of legs."
Princess Diana Hoped Son Prince William Would Emulate JFK Jr
Princess Diana is said to have wanted her son Prince William to turn out like JFK Jr.
Diana, who died nearly two years after their meeting in a Paris car crash, reportedly chose to meet up with JFK Jr. because she greatly admired him for the way he carried himself in the public eye and hoped her eldest son, Prince William, who was just barely a teenager at the time, would adopt some of his admirable qualities.
"I'm hoping he'll grow up to be as smart about it as John Kennedy Jr," Diana told magazine editor Tina Brown, who interviewed the princess just weeks before her death, of William, according to her former assistant Patrick Jephson.
"I want William to be able to handle things as well as John does."
Another reason she allegedly wanted to meet with JFK Jr., who had been recently named the Sexiest Man Alive at the time, was to make her sister-in-law, Sarah Ferguson, jealous.
Superstar singer Madonna recently lauded JFK Jr. in a new interview.
"The princess’s wish to meet America’s most eligible bachelor owed more than a bit to the fact that he was at the time a particular pin-up of Fergie’s," Jephson later wrote.
The late royal isn't the only celebrity once wooed by the political charmer.
Just last month, Madonna named JFK Jr. as her "best d--k down" during her conversation with playwright Jeremy O. Harris, Bob The Drag Queen, dancer Ivy Mugler, designer Raul Lopez, and ID's Marcello Gutierrez.
In a video obtained by Page Six, Lopez grilled her on her "best d--k down," and the pop star clarified, "I'm only going to name dead people," and then covered her mouth as she whispered, "John F. Kennedy Jr."
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The 'Holiday' singer was particularly impressed by his skills in the bedroom.
After their shocked noises and "shut-ups" died down, Lopez added: "Everyone says his d--k was crazy, and he was a good f--k."
Madonna replied: "Mmm hmm," seemingly confirming the rumors.
"You're the third person I've heard say that," the clothing designer noted.
Madonna and JFK Jr. had a brief romance in the 1980s at the height of the Material Girl singer's fame.
"For his part, John, who was not above being star-struck, was dazzled by the notion of dating Madonna, the most glamorous, celebrated, and, by all accounts, exciting woman of her generation," author Christopher Anderson wrote in his 2000 tell-all The Day John Died
