HyperLocal Loop
Jul 16, 2026
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Princess Diana and JFK Jr.’s Secret Meeting

In December 1995, Princess Diana and John F. Kennedy Jr. met in secret at New York City’s Carlyle Hotel. Kennedy hoped to persuade Princess Diana to appear on the cover of his magazine, George. Princess Diana, for her part, wanted to meet the man who had managed to live under intense media scrutiny without being consumed by it.

The Meeting

According to Caroline Hallemann, who wrote about the encounter in her book, The Kennedys & the Windsors, the meeting was a clandestine one. Hallemann spoke with Patrick Jephson, Princess Diana’s private secretary at the time, and Rosemarie Terenzio, JFK Jr.’s executive assistant at George magazine, to hear about what happened in the meeting. Patrick was in the room when they met.

The meeting was purely professional for Princess Diana, who had officially divorced then-Prince Charles. Kennedy was considered the world’s most eligible bachelor at the time. Despite rumors of a romance, the meeting was not a social call, but rather a business discussion. Kennedy thought Princess Diana represented what the magazine was trying to achieve, which was to focus on the intersection of popular culture, politics, and celebrity.

Aftermath

Although Kennedy did not get the answer he was hoping for, Princess Diana left a lasting impression on him. He thought she was quite beautiful and charming. The two spent about an hour together talking, but ultimately, Princess Diana decided not to appear on the cover of George magazine.

Later, rumors claimed that Kennedy and Princess Diana had an affair, but Jephson, who was in the room during the meeting, denied these claims. He described the meeting as a friendly and professional discussion.


Original reporting: Fox News (HLL/CB) — read the source article.

OBBM Network Editorial Staff

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Editorial team behind OBBM Network — independent, hyper-local journalism syndicated through HyperLocalLoop and OBBM Network TV.

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