When JFK Jr. Boldly Flirted With Princess Diana, the Compliment That Left an Impression

John F. Kennedy Jr. once met Princess Diana at the Carlyle Hotel in December 1995, but the private encounter was far from the romantic scenario it might appear to be, as reported by Page Six.

The late magazine founder and son of President John F. Kennedy had reached out to Diana with a professional proposition involving his then-new publication, George.

According to Caroline Hallemann’s book “The Kennedys and the Windsors,” Kennedy arrived prepared, bringing multiple ideas for a cover shoot he hoped would entice the princess.

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One concept showed Diana wearing a three-cornered hat reminiscent of the Revolutionary War era. Another depicted her sitting in the back of a limousine, trying to shield herself from photographers.

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Despite his enthusiasm and the creative ideas, Diana was reportedly uninterested in appearing on the cover before the meeting even began.

Hallemann writes that the princess believed the magazine needed to establish itself as a success before she could publicly support it. Even the Kennedy name, she thought, did not guarantee that George would meet her standards for exposure.

Instead, Diana is said to have gently declined Kennedy’s offer with characteristic grace.

Hallemann recounts that she told him, “Well, you know, this is all very nice, John. Thank you. But I hope you’ll forgive me if I don’t take up the opportunity this time, but would love to maybe for your 50th or your 100th issue or something.”

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After the meeting, Kennedy returned to the George offices and reportedly described the interaction to his team. According to Hallemann, although he admitted defeat, he made a remark that revealed his admiration for the princess.

“Well, she said no,” he told them. “But she had a great pair of legs.”

Some speculated about why Diana had agreed to meet Kennedy in the first place, despite her disinterest in being featured.

One theory was that she admired the way he navigated fame and hoped that her son, Prince William, could learn from his composure and public confidence.

Her former assistant, Patrick Jephson, shared that Diana had told editor Tina Brown, “I’m hoping he’ll grow up to be as smart about it as John Kennedy Jr. I want William to be able to handle things as well

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