John F. Kennedy Jr. and Princess Diana met in secret in December 1995 at New York City's Carlyle Hotel. The meeting, described in Caroline Hallemann's book "The Kennedys & the Windsors," centered on two primary goals: Kennedy's desire for Diana to appear on the cover of his magazine, "George," and Diana's interest in understanding how Kennedy navigated intense media attention.
According to Hallemann, who spoke with Diana's private secretary Patrick Jephson and JFK Jr.'s executive assistant Rosemarie Terenzio, the encounter was kept private despite both individuals being constantly hounded by paparazzi. Jephson was present during the meeting.
Kennedy, then considered the world's most eligible bachelor, was reportedly excited to meet the princess but also annoyed by speculation about their potential romance. For Diana, who had recently separated from Prince Charles, the meeting was professional. She recognized Kennedy's aspiration to bridge popular culture, politics, and celebrity with "George" magazine, and she had already decided against appearing on the cover.
This was not their first encounter; they had met briefly at a luncheon in Virginia during the 1985 royal visit to Washington, D.C. At that earlier event, Kennedy had commented on Diana's "unusual upward glance" and her eyes. Diana, meanwhile, admired Kennedy's mother, Jacqueline Kennedy, as a role model for raising children under the public's gaze.
Plans for the 1995 meeting involved Kennedy potentially using a disguise, which he rejected. The Carlyle Hotel, a place familiar to both Kennedy and Diana, provided discretion. Witnesses described Kennedy as appearing "nervous" and "in awe" of Diana, while she was perceived as "very cool — and jolly, you know, and smiley and welcoming."
During their hour-long conversation, they discussed topics such as Mother Teresa and the paparazzi. Despite Kennedy's hope for a magazine cover feature, Diana tentatively suggested she might consider appearing in a future issue, perhaps the 50th or 100th. She later communicated her decision in a note to Kennedy: "Thank you so much, but not right now," though she reiterated a willingness to appear on a future cover.
Rumors of a romantic affair, including claims of a consummated relationship at the Carlyle Hotel, were dispelled by Patrick Jephson, who stated he was in the room the entire time and observed a "mutual sounding out" that was friendly but not overtly flirtatious.
Kennedy remained interested in featuring Diana in "George," continuing to contact her. In a February 1997 letter, Diana regretfully declined again, expressing empathy for the media's impact on Kennedy and his wife, Carolyn Bessette Kennedy.
Princess Diana died in a Paris car crash on August 31, 1997, at age 36, an event pursued by paparazzi. Her death deeply affected JFK Jr., who saw parallels between her experience and his own family's struggles with media scrutiny. Carolyn Bessette Kennedy was also significantly distressed by Diana's death and her own encounters with the press.
John F. Kennedy Jr. and Carolyn Bessette Kennedy died in a plane crash on July 16, 1999. Hallemann suggests that the enduring public fascination with both Diana and JFK Jr. stems partly from their youth, the intense media scrutiny they endured, and their shared status as individuals who, for a brief moment, connected away from the spotlight.