“Diana wanted it to be discreet because it had all the makings of a great gossip story.”

Princess Diana and Sarah Ferguson were known to be one of the royal family’s best friends, but there was a major moment that could only have happened between two people who knew how to push each other’s buttons. Back in December 1995, Diana had a meeting with John F. Kennedy Jr., who was hoping that she’d appear on the inaugural cover of his magazine, George. The meeting at the Carlyle Hotel is now the stuff of legend—that happens when two of the most famous people in the entire world cross paths—but insiders say that while Diana was considering it, part of why she wanted to meet Kennedy was to make Ferguson jealous.

“Sarah Ferguson had the hots for him and Diana wanted to, I think, do one-up on her,” Patrick Jephson, Diana’s secretary, explained.

RoseMarie Terenzio, author of the new book JFK Jr.: An Intimate Oral Biography, gave an insider’s perspective on the situation and detailed the arrangements that she had to make with Jephson to have the meet-up run smoothly.

“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?” However, Kennedy went through the front door and evaded photographers because they gathered at the hotel’s side door, presuming that Diana would find an alternative to the main entrance.

“He went right in without being noticed,” Terenzio shared.

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Jephson convinced Diana to pass on the opportunity, telling her that she’d be a better choice for the magazine after it established itself.

“That was why we thought she would do the twentieth or the fiftieth or the hundredth issue or something,” Jephson shared in the book. “The message was clear: you make a good job of the magazine, and I’ll think about it.”

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He also shared that Diana had a bit of fun with the whole situation, knowing that it would have made headlines if anyone knew about it—which is why it was kept secret for so long.

“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 and then-Prince Charles finalized their divorce in August 1996. Kennedy and Caroline Bessette would go on to marry in September 1996.