JFK Jr. and Diana's secret meeting fueled romance rumors
In December 1995, JFK Jr. secretly met Princess Diana at New York's Carlyle Hotel to pitch a George magazine cover. She declined, but their private hour together—confirmed by her secretary Patrick Jephson—sparked romance rumors for decades. A new book says it was mainly business, not a love affair.
Key Takeaways
- JFK Jr. and Princess Diana held a clandestine December 1995 meeting at New York City's Carlyle Hotel.
- He wanted her on the cover of George; she declined but stayed for about an hour of conversation.
- Diana's private secretary Patrick Jephson was in the room and disputes affair rumors.
- Author Caroline Hallemann details the encounter in The Kennedys & the Windsors.
- They stayed in touch by letter until Diana's death in 1997.
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What happened at the Carlyle Hotel meeting?
According to Fox News, reporting on Caroline Hallemann's book The Kennedys & the Windsors, the world's two most famous figures met in secret in December 1995.
John F. Kennedy Jr., co-founder and editor-in-chief of George, hoped to land Diana for a cover. The magazine had launched that September and aimed at the intersection of popular culture, politics, and celebrity.
Diana, newly navigating life after her separation from then-Prince Charles, wanted to meet the man who lived under intense scrutiny without being consumed by it. Jackie Kennedy had long been a role model for how to raise children in the public eye.
Jephson and Rosemarie Terenzio, JFK Jr.'s executive assistant at George, helped Hallemann reconstruct the night. Jephson was actually in the room. The hotel's discretion was "extraordinary," and Kennedy refused any paparazzi disguise.
Was the JFK Jr. and Diana meeting a romance?
Rumors later claimed an affair consummated at the Carlyle in a "moment of pure lust." Jephson told Hallemann he stayed throughout and saw no passionate activity—only a "mutual sounding out" that was friendly, not overtly flirtatious.
Hallemann wrote that Kennedy was excited to meet the royal yet annoyed by talk of a "marriage made in heaven." For Diana, sources say the sit-down was framed as professional from the start, even though she already planned to say no to the cover.
An AOL report citing Jephson also noted a "flirtatious" element and said Diana may have wanted to make sister-in-law Sarah Ferguson jealous. He added she saw Kennedy as "rather vulnerable," not only as a famous bachelor.
When they met face to face, Jephson said Kennedy seemed "quite in awe." Diana was "very cool" — jolly, smiley, and welcoming. They spoke about Mother Teresa and the paparazzi, among other topics.
Why did Diana turn down the George magazine cover?
Kennedy believed Diana embodied what George stood for. After about an hour—or roughly 90 minutes, per some accounts—she gave Jephson "a sly glance" and suggested she might consider the 50th or 100th issue instead. Her decision that day was final.
She later sent a note: "Thank you so much, but not right now." Kennedy kept asking. In February 1997 she wrote again, "regrettably" declining, and hoped the media would leave him and wife Carolyn alone.
They had crossed paths earlier at a 1985 Virginia luncheon during a royal visit to Washington. Kennedy once told friend Billy Noonan that Diana had "the most unusual blue eyes" and a "really seductive" upward glance. After the Carlyle meeting, he reportedly told staff she said no—but "had a great pair of legs."
Diana died in a Paris crash on Aug. 31, 1997, at 36. Hallemann said the loss shook JFK Jr., who saw media scrutiny as a shared burden, and deeply rattled Carolyn Bessette Kennedy. He and Carolyn died in a plane crash on July 16, 1999.