In the end, John and Diana spent “a pleasant enough” hour or so together. “I remember he felt like it was more fun than he had expected in the royal meeting, a little more genuine,” Sasha said. “I think he liked her, put it that way.” And despite later rumors that the couple had an affair that was consummated at the Carlyle that day in a “moment of pure lust,” Patrick said he remained in the room the whole time. “I stayed in the room throughout and was not aware of any mad, passionate activities,” he said. “My observation was, it was a kind of mutual sounding‑out. It was a kind of appraisal, and it wasn’t overtly flirtatious, but it was friendly.”
Prior to the meeting, Patrick and Diana had discussed how long to let the conversation go on. When it reached that point, Patrick interrupted, apologizing, and saying something like, “We’ve got to get ready for the next thing,” giving the princess an out.
As John made his way back downstairs, Diana turned to Patrick and said “words to the effect of ‘That went well, and it was the right thing to do.’”
“I can’t remember the words, but there was a degree of sympathy. I think she might have spoken about the famous picture of him as a little boy. And she had sympathy for him growing up with the name and being the object of public fascination. These were things that she could relate to. I definitely picked up a sense of sympathy, of concern, for him. She didn’t see him as the rest of the world saw him. As this big, famous, handsome guy. She saw him, I think, as rather vulnerable because he had grown up in public,” Patrick would later recall.
But while the ask to appear on an early cover was denied, John didn’t leave the hotel entirely empty‑handed; Diana wrote him a note, which read, “Thank you so much, but not right now.” And again she had agreed to consider appearing on a future cover of George, possibly enjoying the tease of being able to say yes in principle, but that they’d have to wait.
As John exited the hotel, his assistant asked the obvious question: “Well, how was she?”
“She’s tall, taller than I thought,” he said. “She’s very nice, shy, a little coy. But she’s not going to do it.”
“I could tell he was disappointed that she said no,” RoseMarie said.
And with that, they trekked back to midtown to the George offices. “What was she like?” a chorus of editors asked upon their arrival. As he dropped the imagined cover sketches back on Matt Berman’s desk, John said, “Well, she said no, but she had a great pair of legs!” From there, John kept things light, never lingering on the disappointment.
“At the end of the day, all he cared about was getting a yes to the cover of George,” RoseMarie said. “Everything else was kind of, whatever.”
The Kennedys and the Windsors: The Story of Two Dynasties, One Born, One Made
Cindy Crawford in a midriff‑baring George Washington–meets–pinup girl ensemble was featured on the cover of the debut issue of George, which John revealed at a press conference at Manhattan’s Federal Hall in September 1995. When the suggestion of Crawford initially came up, John’s future wife, Carolyn Bessette, insisted it was the right call. “She’s all‑American, a self‑made woman, sexy, strong, and smart,” Carolyn said, in an opinion shaped by her years of work-ing in fashion PR. She was right. The image was instantly iconic, and it set a precedent for the magazine. But despite the inherent Americanness of George, John continued to think about how Princess Diana could be a part of the magazine, and she was still mentioned within its pages quite often. In the August 1997 issue, for example, Marla Maples appeared on its signature “If I Were President” page, answering the question “What foreign problem would you like to solve?” with “Princess Di’s peace of mind.” The September 1997 issue, which went to print a few weeks before Diana’s untimely death, included a photo of her alongside Elizabeth Dole at a Red Cross event for land mine survivors. The two women were also pictured together in the final issue John edited.
