Did John F. Kennedy Jr. Have A Relationship With Princess Diana?

The affairs of JFK may have been kept from wide public knowledge in his lifetime, but now they're as much a part of the mythology surrounding his presidency as the Bay of Pigs and the Cuban Missile Crisis. The stories of his infidelities have outstripped verifiable facts; his dalliance with Marilyn Monroe was so brief that her biographer Donald Spoto (via "Marilyn Monroe") felt it couldn't even constitute an affair. But it does appear to have happened, along with plenty of other reported encounters.

A reputation for a wandering eye attached itself to JFK's son as he came of age, though not quite in the same way. Part of John F. Kennedy Jr.'s allure to the press was his status as a bachelor, and he was even dubbed "America's most eligible bachelor" in 1986 by People magazine (via UPI). But when he tied the knot with Carolyn Bessette, he appeared to outside observers to remain a faithful husband. In his 2019 book "America's Reluctant Prince: The Life of John F. Kennedy Jr.," Kennedy Jr.'s friend Steven M. Gillon insisted that the politician, while troubled by his stormy marriage at times, was determined not to be the philanderer his father was.

Yet in the years since his and Bessette's untimely deaths, rumor has suggested he might have had at least one affair. It was reported by The Sun in 2005 and lingers around the internet (via NBC News). The story goes that Kennedy, a family often called America's royalty, carried on with a member of the British royal family: Princess Diana.

Diana's friend claimed she was told about the affair

The claim that John F. Kennedy Jr. and Princess Diana had an affair was made by the icon's friend and "energy healer" Simone Simmons in her book "Diana: The Last Word," excerpted in The Sun before publication. Simmons claimed that Diana confided the affair in her. Kennedy and Diana came into contact in New York in 1995, when Kennedy was soliciting interviews for his magazine, George. At that time, Kennedy was not yet married, but he and Carolyn Bessette had been dating for a year (per Harper's Bazaar). Meanwhile, Diana was by that time separated from the then-Prince Charles but still a year away from her divorce.

According to Simmons, Diana turned down the interview request but agreed to see Kennedy socially. They met in the Carlyle Hotel, which the Daily Mail claimed was the site of John Sr.'s dalliance with Marilyn Monroe. The princess, whom Simmons says was "very circumspect in her courtships and approached them cautiously," fell into a fit of lust in Kennedy's presence and engaged in a passionate one-night stand. It was supposedly a delightful experience for Diana, who was thrilled to have successfully seduced an attractive man. Simmons claims that Diana kept a rating system for her lovers — and she put Kennedy at the very top.

There is no evidence for the fling

It has been confirmed that John F. Kennedy Jr. sought Princess Diana for his magazine, George. In 2017, the magazine's then-creative director Matt Berman told People that the politician wanted her for a cover photo, not an interview, and that their meeting at the Carlyle Hotel was about the potential shoot. The staff at George were well aware of the visit and had prepared preliminary materials that Kennedy brought with him. At the time, the concern among Kennedy's staff and friends wasn't any covert affair — it was the fact that he and Diana were two of the most famous people in the world at the time, and keeping the meeting private was a near-impossible task.

Kennedy's executive assistant, RoseMarie Terenzio, told People that she worked with him to plan out how he would get into the Carlyle based on where the paparazzi were most likely to be stationed (the trick was to walk openly in through the front instead of sneaking in from the side door). By Terenzio's account, the meeting lasted an hour and a half and ended with a polite "no." She recalled Kennedy being surprised at how shy Diana was. He was apparently surreptitious about the meeting and may have remarked on her height and her "great pair of legs," as Berman put it (via "JFK Jr., George, & Me."), but no one remembered him discussing an affair. On Diana's end, friends of hers told NBC News and the Daily Mail that Simone Simmons' story about the affair was untrue, and indeed, the author offered no evidence but her own claim.