When J.F.K., Jr. Met Princess Diana: How They Pulled Off a Top Secret New York City Encounter
July 5, 2021
He was American royalty and she was actual royalty—and somehow, in 1995, they met in New York City undetected.
People reports that J.F.K., 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, you know, 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: In God’s name, how?
J.F.K., Jr.’s executive assistant RoseMarie Terenzio recalls 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 J.F.K., 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 brass 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 she 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 Theresa so they spoke about that. And he said how lovely she was.” Matt Berman, George’s former creative director, remembers him saying, “She’s got a great pair of legs.”
So, next time you have an idea you can’t tell if is really brilliant or really stupid (come on, we’ve all got that “App ideas” note on our phone), maybe just go for it. After all, the front door did work for Diana and J.F.K., Jr.