‘Love Story’: Did JFK Jr. and Carolyn Bessette-Kennedy Actually Meet Princess Diana?

What is known, though, is that JFK Jr. met Princess Diana in 1995, in a secret meeting in New York City.

According to People, JFK Jr. wanted Diana, then separated from Prince Charles, to pose for the cover of his political magazine George. She agreed to hear him out—but in order to do that, they had to talk first. Easier said than done when both parties leave a swarm of paparazzi in their wakes.

After a lot of clandestine diary finagling, they agreed to meet one summer day in a suite at the Upper East Side’s posh Carlyle Hotel. But although the when and why was decided, the bigger question remained: How?

JFK Jr.’s executive assistant RoseMarie Terenzio recalled that even her boss thought there was no way it could ever work. “I remember him saying, ‘There’s no way someone is not going to leak it. There’s going to be paparazzi everywhere,’” she said.

Like a quintessential spy movie montage, Kennedy’s inner circle started hatching a plan on how to hide the president’s son and a princess. “Someone suggested he go in disguise and I said, ‘That’s ridiculous. You’re not doing that!’” Terenzio remembers.

The end plan was simple: They decided JFK Jr. and Diana should walk in the front door.

Their logic was this: If the press found out about the meeting, which was inevitable, they’d assume the two celebrities would use the less-visible side entrance. Because surely they wouldn’t think they would be so brash as to use the front entrance, right?

But, as the saying goes, fortune favors the bold: When they pulled up, they were right—all the press was at the side door. And the two waltzed right in.

They met for an hour and a half, but Princess Diana didn’t end up posing for George magazine. However, his staff can recollect some tidbits about the fateful encounter: “I do remember him saying, ‘She’s really tall!’ He also said she was very shy. He was surprised how demure she was,” says Terenzio. “I think they had both met Mother Teresa, so they spoke about that. And he said how lovely she was.”