At the time, John hoped to convince Diana to pose for the cover of his political magazine George.
“We had to draw all these cover ideas up, and he took the drawings over to the Carlyle Hotel to meet her,” George magazine creative director Matt Berman, who made the sketches, tells PEOPLE.
The day of their meeting, RoseMarie Terenzio, John’s executive assistant and a close friend who recounted their years together in her 2012 memoir Fairy Tale Interrupted, accompanied him to the Carlyle.
“I remember him saying, ‘There’s no way someone is not going to leak it. There’s going to be paparazzi everywhere,’ ” Terenzio recalls. “Someone suggested he go in disguise and I said, ‘That’s ridiculous. You’re not doing that!’ ” He agreed.
Terenzio and JFK Jr. discussed which of the two hotel entrances to the famed hotel would attract the least attention. “I had remembered that the last time I had been to the Carlyle for an event, there had been no photographers at the front entrance,” says Terenzio.
“So I told John, ‘Don’t go in the side entrance, because if anyone does leak it beforehand, people will expect you to go in the side. So walk in the front door.’ ”
And that’s exactly what happened: As they pulled up to the front of the Carlyle, the two megastars walked right in. “All the press was on the side door!” recalls Terenzio with a laugh.
The meeting took place in Diana’s suite and lasted about an hour and a half. “He wanted to do a respectful piece,” Terenzio recalls. But it was not to be. Says Terenzio: “She wrote John a note that said, ‘Thank you so much, but not right now.'”
Afterward, he told his George colleagues about their meeting. “He was very careful what he said,” recalls Berman, who wrote about the encounter in his 2014 memoir JFK Jr., George, & Me. “The one funny thing he said was, ‘She’s got a great pair of legs.’ “
Looking back, Terenzio says, “I do remember him saying, ‘She’s really tall!’ He also said she was very shy. He was surprised how demure she was. I think they had both met Mother Theresa so they spoke about that. And he said how lovely she was.”
For more on Carolyn Bessette Kennedy, pick up a copy of this week’s PEOPLE.