For one brief, shining moment in December 1995, the two most famous people in the world at the time—Princess Diana and John F. Kennedy Jr.—met at New York City’s Carlyle Hotel. John had an ask to make of Diana—would she appear on the cover of his new magazine, George? She had appeared—infamously now—on BBC’s Panorama with Martin Bashir, so John thought maybe she’d be open to more media appearances; he wanted her to dress up as an American historical figure, according to his executive assistant RoseMarie Terenzio, who wrote the brand new book JFK Jr.: An Intimate Oral Biography with Liz McNeil, its release timed with the 25-year anniversary of John’s death in a 1999 plane crash alongside his wife, Carolyn Bessette-Kennedy, and his sister-in-law, Lauren Bessette.
After John wrote Diana a letter, the Princess of Wales responded by saying she’d like to talk about the ask in person—and that she’d be in New York City and staying at the Carlyle. Terenzio and Diana’s private secretary Patrick Jephson made the arrangements for the two to meet on a weekday afternoon.
“There was all this worry,” Terenzio wrote. “Should he go in the front door? Should he wear a disguise, because won’t there be rumors that he’s having an affair with her?” Ultimately, John decided to just walk in the front door—the paparazzi were all camped out at the side door waiting for Diana, anyway. “He went right in without being noticed,” Terenzio added.
Jephson advised Diana against doing the cover until George had time to establish itself—after all, its first issue date was September 1995, just three months before this meeting. “That was why we thought she would do the twentieth or the fiftieth or the hundredth issue or something,” Jephson said in the new oral biography. “The message was clear: you make a good job of the magazine, and I’ll think about it.”
Of the meetup with John, “It was never made public, so that made it quite fun, actually,” Jephson said. “Diana wanted it to be discreet because it had all the makings of a great gossip story, didn’t it? World’s most eligible bachelor, wasn’t he at the time? And she had just got unmarried or was in the process of getting unmarried. It would’ve been a rather intriguing thing to dream about.”
Diana had separated from Prince Charles in 1992, and their contentious divorce would finally wrap up in August 1996, eight months after meeting up with John. But John was already spoken for—he and Carolyn were very much together, and would marry in September 1996.
Diana was especially into the meeting with John because, like pretty much all women alive in December 1995, “Sarah Ferguson had the hots for him and Diana wanted to, I think, do one up on her,” Jephson said. (Ferguson was in the middle of her own divorce from Prince Andrew, which would also be settled after four years’ time in 1996.)
The two both wore business attire and had a drink—John “was quite in awe of her,” Jephson said. “Not uncomfortable, but he certainly seemed to be on his best behavior. He rather sat on the edge of his chair and looked nervously at her.” But Diana “was not nervous at all to meet him,” he added. “She was very cool—and jolly, you know, and smiley and welcoming.”
Except, unfortunately for John, Diana was less welcoming to the idea of appearing on the cover of George. He accepted her decline “without fuss,” Jephson said, adding that he could sense Diana had a sense of sympathy and concern for him. “She didn’t see him as the rest of the world saw him,” Jephson said. “As this big, famous, handsome guy. She saw him, I think, as rather vulnerable because he had grown up in public.” After all, Diana was raising two young boys who, like John, never knew life without cameras permanently fixated on them.
Gorgeous though he was, “She didn’t comment on his looks,” Jephson said, adding “She was used to being judged by her looks, and therefore didn’t have much time for it.” But John did comment on Diana’s looks, telling Terenzio “She’s much taller than I thought—and she’s got great legs.”
The two kept in touch after their meeting through letters, and at one point, he asked her for an interview for George. In a letter from February 3, 1997, Diana wrote to John from Kensington Palace politely declining the interview, and adding “I hope”—and she underlined the word “hope,” Terenzio specified—“the media are leaving both you and Carolyn alone. I know how difficult it is, but believe it or not, the worst paparazzi are here in Europe!”
Diana was dead seven months later.
When it came to covering her death in the pages of George, John refused to do so. And Diana’s death—in a Parisian car accident while being chased by the paparazzi—only heightened his wife Carolyn’s fear of them. “She was saying to John, ‘See, I’m not blowing this out of proportion,’” Terenzio wrote. “‘They’re dangerous.’” Carolyn was also known to say of the paparazzi, per the oral biography, “I’m terrified of them.”
Just shy of two years after Diana’s tragic death at age 36, John, Carolyn, and Lauren died in a plane crash in the Atlantic Ocean; they were just 38, 33, and 35 years old, respectively. In less than four years’ time, the two most famous people on the planet—barely in their mid-thirties at the time—had gone from tea and champagne at the Carlyle, to becoming, inexplicably and tragically, just a memory.
