John, 35, was hoping to persuade the princess, 34, to appear on the cover of his new magazine, George. After meeting JFK Jr. in a quiet corner of the lobby, Diana’s private secretary Patrick Jephson escorted him to the princess’s suite, where the pair sat down over coffee.<\/p>\n
\u201cIt was a little bit cloak and dagger,\u201d Jephson tells PEOPLE in this week’s cover story, which explores the surprising ties<\/a> between the Kennedys and the Windsors.<\/p>\n Following Jephson\u2019s advice that appearing in the magazine would amount to giving the fledgling publication \u201ca seal of approval it didn\u2019t yet merit,\u201d Diana politely declined, but she suggested she might consider appearing for the magazine\u2019s 50th or 100th issue.<\/p>\n But the encounter itself left an impression. \u201cI sensed a vulnerability in him,\u201d recalls Jephson. \u201cWhen 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.\u201d<\/p>\n Princess Diana leaves the Carlyle hotel in New York City. on December 11, 1995 Despite his own celebrity status, John was not immune to Diana\u2019s star power. \u201cI spent eight years seeing people who might consider themselves important and famous become like jellies when presented to the princess,\u201d says Jephson.<\/p>\n Diana, meanwhile, was well aware of John\u2019s appeal. Named PEOPLE\u2019s Sexiest Man Alive in 1988<\/a>, he was one of America\u2019s most sought-after bachelors.<\/p>\n \u201cThere was anticipation on both sides,\u201d Jephson says. Diana, dressed for a working engagement later that day in Manhattan, was her usual charming self.<\/p>\n John F. Kennedy Jr at the launch of his magazine George in New York City, in Sept. 1995 \u201cShe was\u00a0quick-witted and fun to be with,\u201d Jephson says. \u201cIt 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.\u201d<\/p>\n By the end of the meeting, two defining figures of their era had shared a rare moment away from the spotlight.<\/p>\n \u201cThey parted on warm terms,\u201d Jephson says.<\/p>\n George magazine gave John an opportunity to forge an identity beyond the political dynasty that had made his family famous. Decades later, Diana’s younger son, Prince Harry, would also pursue a different kind of independence, stepping back from royal duties with his wife, Meghan Markle, and building a new life in California.<\/p>\n “They were trying to forge their own path outside of their families\u2019 legacies. But they both floundered,” says author Caroline Hallemann, whose new book\u00a0The Kennedys & the Windsors<\/a>\u00a0explores the surprising intersections between the most famous political dynasty in the U.S. and Britain\u2019s royal family.<\/p>\n This week’s issue of PEOPLE<\/p>\n Can’t get enough of PEOPLE’s Royals coverage? Sign up for our free Royals newsletter<\/a> to get the latest updates on Kate Middleton, Meghan Markle and more!<\/p>\n This week’s PEOPLE cover story explores the lasting legacies of Princess Diana and JFK Jr.’s wife Carolyn Bessette Kennedy<\/a>, as well as the relationships between Queen Elizabeth and Jackie Kennedy.<\/p>\n \u201c[Those women] had great proximity to power and soft diplomacy but not true political power behind them,\u201d Hallemann tells PEOPLE.<\/p>\n The fascination surrounding both families remain as culturally potent as ever. FX recently revisited the romance of John and Carolyn in the hit series\u00a0Love Story, while Netflix is filming a Kennedy drama widely seen as a potential American counterpart to\u00a0The Crown.<\/p>\n \u201cHollywood keeps this idea of them being America\u2019s First Family alive as well,\u201d Hallemann adds.<\/p>\n![\"Princess](\"https:\/\/www.newsbeep.com\/us-ny\/wp-content\/uploads\/2026\/06\/aa7cb467e83167d04947e44b2c6d0f52.jpeg\"\/)
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Credit: AP Photo\/Kathy Willens<\/p>\n![\"John](\"https:\/\/www.newsbeep.com\/us-ny\/wp-content\/uploads\/2026\/06\/9caf67f06fa9b579696b4d7641890246.jpeg\"\/)
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Credit: Steve Allen\/Liaison<\/p>\n![\"This](\"https:\/\/www.newsbeep.com\/us-ny\/wp-content\/uploads\/2026\/06\/706a22eea783c4c3b06a4b4f34b22e08.jpeg\"\/)
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