Were Princess Diana and JFK Jr. Romantically Involved? Everything to Know About Their Secret NYC Meeting

Princess Diana and John F. Kennedy Jr. shared one brief but intriguing meeting in the 1990s.

When the businessman unveiled George, a monthly political lifestyle magazine, in September 1995, he immediately thought that a cover featuring the People's Princess would be a major commercial and editorial coup.

"It seems obvious why [JFK Jr.] would've wanted her on the cover, because he was trying to capture the intersection of political life and celebrity life in his magazine," the attorney's close friend Sasha Chermayeff shared in Caroline Hallemann's book The Kennedy and the Windsors: The Story of Two Dynasties, One Born, One Made.

"Lady Di, at that moment, was a perfect example of that because she was a symbol of the intersection of those things," she added. "She was a celebrity, a royal who had a defined role, but she also had a personal and political mission. She had ideas about how she wanted to help the world. She had her own feelings about her service, at least that's the perspective that I got from her. She was loved by America, too. We loved her, everybody loved her."

JFK Jr. then sent Diana a letter requesting a meeting, and the royal agreed to meet with him.

Diana was scheduled to receive a humanitarian award at the United Cerebral Palsy Awards gala, just weeks after her Panorama interview about her troubled marriage to then-Prince Charles.

The then-Princess of Wales and JFK Jr. ultimately met in secret at New York City's Carlyle Hotel in December 1995.

"We agreed that she would find time in her program in New York to meet him. Nobody wanted it to be public," Diana's private secretary Patrick Jephson, who escorted JFK Jr. to the suite, said in Hallemann's book.

He noted JFK Jr. was "quite in awe" of Diana during the meeting, adding, "Not uncomfortable, but he certainly seemed to be on his best behavior… She was very cool — and jolly, you know, and smiley and welcoming."

When JFK Jr. floated the idea, Diana respectfully turned down the proposal but said she would consider it in the future.

Chermayeff recalled, "I remember he felt like it was more fun than he had expected in the royal meeting, a little more genuine. I think he liked her, put it that way."

Meanwhile, Jephson added, "I stayed in the room throughout and was not aware of any mad, passionate activities. 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."

Jephson's statements in the book mirrored what he told People about the meeting.

"She was quick-witted and fun to be with," he said of Diana. "It was a little bit flirtatious, as she would have been with any man. But because he was who he was, that gave it a slight extra sparkle."

He later added, "They parted on warm terms."

RoseMarie Terenzio, who previously worked as JFK Jr.'s executive assistant and the chief of staff at George, confirmed the magazine publisher and Diana "stayed in touch" after the New York City meeting.

While it is not known whether they ever met again, Terenzio said JFK Jr. continued to ask Diana for an interview for George. Meanwhile, the royal princess responded in a letter from Kensington Palace dated February 3, 1997.

According to the multimedia communications executive, Diana thanked JFK Jr. for his correspondence but once again declined the opportunity.

"'I hope' — and she underlined 'hope' — 'the media are leaving both you and Carolyn alone. I know how difficult it is, but believe it or not, the worst paparazzi are here in Europe!'" Terenzio shared the end of Diana's letter.

When Diana was killed in a fatal car crash in Paris, France, on August 31, 1997, Carolyn urged her husband to call Prince William and Prince Harry.

"That dissonance in grief was something John understood — and when Carolyn heard the news of Diana's death, she urged him to call William and Harry to offer his condolences," Hallemann wrote in her newly released book. "John was one of the few people who could truly empathize with what Diana's sons were going through — having to put on a brave face while publicly mourning."

"Not only because of his experience at his father's funeral, and just a few years later at that of his uncle Bobby, but also because he was still fresh in his grief over his own mother. But after thinking about it, he decided against calling the princes, given that they were not particularly close."

Diana's car crash and her connection with the couple were also featured in FX's Love Story.

On July 16, 1999, almost two years after Diana's death, JFK Jr. and Carolyn — alongside the fashion publicist's older sister, Lauren — were killed when their plane plunged into the Atlantic Ocean.