The day JFK Jr propositioned Princess Diana... part of her body he found irresistible... and crippling fear that sent Carolyn Bessette into a spiral

By RUTH WALKER, U.S. BOOKS EDITOR Published: 14:41, 6 June 2026 | Updated: 14:41, 6 June 2026 They were two of the most eligible people on the planet, having an intimate rendezvous at a storied New York hotel. But John F Kennedy Jr and a newly separated Princess Diana were not having a romantic assignation - much to the disappointment of fans who saw the pairing as a match made in celebrity heaven. Instead, Kennedy was wooing Diana for a very different reason - to persuade her to pose for the cover of his new political lifestyle magazine George. And a new book has revealed exactly what happened during that top secret meeting - and the mischievous reason Diana met with, and ultimately turned down, the Sexiest Man Alive. According to The Kennedys and the Windsors by Caroline Hallemann, John Jr was nervous about meeting the princess in the December of 1995 but didn't waste any time on small talk as he made his pitch. 'John had brought along with him several ideas for the cover shoot,' writes Hallemann. 'One featured her wearing a three-corner hat like one from the Revolutionary War, another, oddly enough, showed her in the back of a limousine with the window rolled halfway up, in an attempt to avoid photographers.' That vision was to prove tragically prescient as the princess famously died less than two years later as her drunk driver attempted to evade paparazzi in Paris. Diana was newly separated from Prince Charles when she met Kennedy at the Carlyle Hotel; John had brought along with him several ideas for the proposed cover shoot Around the time of their meeting, Kennedy had been anointed the Sexiest Man Alive John Jr didn't know it but, the conversation was apparently over before it even started, as the book reveals, Diana had already made up her mind to refuse him. 'She needed the magazine to be a success before she'd publicly front it,' writes Hallemann, 'and even with a Kennedy at the helm of the publication, that was hardly a guaranteed prospect.' She quotes the princess as saying: '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.' So why did she take the meeting with Kennedy in the first place? According to her private secretary Patrick Jephson, who was present at the time, and magazine editor Tina Brown, who interviewed the princess just weeks before her death, one of the reasons was because she admired the way Kennedy coped with life in the spotlight and wanted to emulate that for her sons William and Harry. 'I'm hoping he'll grow up to be as smart about it as John Kennedy Jr,' Diana had told Brown of William. 'I want William to be able to handle things as well as John does.' But there was another, altogether more naughty explanation for agreeing to the meeting: she allegedly wanted to make her sister-in-law Sarah, the Duchess of York and then wife of the now disgraced Andrew Mountbatten-Windsor, jealous. '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 pair may not have hit it off romantically, but Kennedy was still at least a little smitten by the glamorous Diana. When he got back to the offices of George, he was met with a chorus of questions: 'What was she like?' his editors wanted to know. 'Well, she said no,' Kennedy told them. 'But she had a great pair of legs.' One of the reasons Diana wanted to meet John Jr was because she wanted to emulate the way Jackie had raised her children in the spotlight (photographed with William) 'I want William to be able to handle things as well as John does,' she once said (Jackie photographed with John Jr in 1967) She may have refused JFK Jr, but he was still taken by Diana's legs, he told editors at George Hallemann's book examines the parallels between both dynasties - the Windsors and Kennedys; one born, one made - as well as the surprising bonds that developed between them. One occasion that took the author by surprise was a sweetly human moment on the day of President John F Kennedy's funeral in November 1963. Jackie Kennedy was hosting an event for diplomats in the White House following the service at Arlington. For most of the day the grieving First Lady had kept her composure, but when Irish president Eamon de Valera quoted a moving Gerald Griffin poem - one President Kennedy had memorized and which spoke of a river returning to its home - 'her polished facade… fell, and she started to cry.' Writes Halleman: 'Ducking into her husband's bedroom for a moment alone to compose herself, she was surprised and a little embarrassed to find her son playing with Prince Philip on the floor. Philip, blushing, immediately shared that John Jr reminded him of his own son. '"I've got one like that," he had told the Kennedys' nanny Maud Shaw earlier in the reception when he saw her chasing John Jr down the second-floor corridor. "They're a handful, aren't they?" 'Jackie quickly regained her composure. "John, did you make your bow to the Prince?" she asked, dipping into her own curtsy. 'John, who had turned three years old that day, proudly proclaimed that he had, and any remaining awkwardness instantly vanished as the group had a laugh over his enthusiasm.' The bond between the famously curmudgeonly prince and the little boy must have continued as, in March 1965, as the UK unveiled its own memorial to the assassinated president at Runnymede, Surrey, the pair were pictured holding hands as they walked through the woods towards the large plaque. When the UK unveiled its own memorial to the assassinated president at Runnymede, Surrey, Prince Philip and John Jr were pictured holding hands John Jr salutes the Royal Guardsmen at Buckingham Palace during their visit in May 1965 Caroline Kennedy curtseys for the Queen at the dedication of the memorial to her father However, one of the most poignant connections revealed in the book concerns a terrifying premonition of John Jr's wife Carolyn Bessette following Diana's death in Paris, age 36. Carolyn was already haunted by fears that the press attention of the couple might lead to something more sinister. But following the tragedy in the Pont de l'Alma tunnel in August 1997, her paranoia reached fever pitch, and John Jr's personal assistant recalled that he seemed to be in denial about the whole thing. 'Instead of talking about Diana with the editors [at George], he started cleaning out his office files, throwing them into a big dumpster,' recalled RoseMarie Terenzio.  'I think he thought, "This is going to push my wife over the edge even more."' Hallemann continues: 'To hear that Diana, who just a month prior had sat one pew in front of her at their mutual friend Gianni Versace's funeral, had died being chased by photographers would have been distressing fuel for Carolyn's anxiety and frustration about the press.' Diana's death persuaded Carolyn that she, too, might meet the same fate and it pushed her to breaking point as she became increasingly reclusive. 'She just didn't want to leave the apartment,' John's old schoolfriend Sasha Chermayeff said. 'She didn't want to go out and be followed.' Carolyn was haunted by fears she and John Jr might succumb to the same fate as  Diana Following Diana's death in the Pont de l'Alma tunnel in August 1997, Carolyn's paranoia reached fever pitch John Jr famously salutes his father's coffin following his funeral in November 1963 Princes William and Harry echoed the moment in September 1997, following their mother's death She did, however, attempt to persuade John Jr to call princes William and Harry to offer his condolences, the book reports. 'John was one of the few people who could truly empathize with what Diana's sons were going through - having to put on a brave face while publicly mourning. Not only because of his experience at his father's funeral, and just a few years later at that of his uncle Bobby, but also because he was still fresh in his grief over his own mother [who died in May 1994].' In the end, however, he decided not to call the young princes, because he didn't know them particularly well.  Two years later, Carolyn's eerie premonition came true, as she, John Jr, and her sister Lauren were all killed in a plane crash off the coast of Martha's Vineyard. Kennedy was 38 and Carolyn just 33. The Kennedys and the Windsors - The Story of Two Dynasties, One Born, One Made by Caroline Hallemann is published by GP Putnam's Sons No comments have so far been submitted. Why not be the first to send us your thoughts, or debate this issue live on our message boards. By posting your comment you agree to our house rules. Do you want to automatically post your MailOnline comments to your Facebook Timeline? Your comment will be posted to MailOnline as usual. Do you want to automatically post your MailOnline comments to your Facebook Timeline? Your comment will be posted to MailOnline as usual We will automatically post your comment and a link to the news story to your Facebook timeline at the same time it is posted on MailOnline. To do this we will link your MailOnline account with your Facebook account. We’ll ask you to confirm this for your first post to Facebook. You can choose on each post whether you would like it to be posted to Facebook. Your details from Facebook will be used to provide you with tailored content, marketing and ads in line with our Privacy Policy.