John F. Kennedy Jr. Once Proposed to Princess Diana

In December 1995, John F. Kennedy Jr. reached out to Princess Diana for a meeting at the Carlyle Hotel, but it was far from romantic.

He had an idea for his new political lifestyle magazine, George, and wanted Diana to be its cover star. According to Caroline Haleman’s book, *The Kennedys and the Windsors*, Kennedy approached her with some concepts for the cover shoot. One idea featured her in a tricorn hat resembling those from the Revolutionary War, while another showed her in a limousine, deliberately positioned to avoid paparazzi.

However, Diana, who was attending a gala at the time, wasn’t keen on being featured. She had made up her mind before Kennedy even pitched his proposal. Haleman mentions that Diana felt the magazine needed to establish itself before she could join in its publicity. With uncertainty surrounding its potential success, she politely declined, telling Kennedy she might be open to a future issue.

When Kennedy returned to his office, he shared that the opportunity with Diana was off the table but still expressed intrigue about the collaboration.

Despite the rejection, Kennedy relayed his thoughts to his team, stating, “Well, she said no. But she had great legs.”

Interestingly, it seems Diana actually admired Kennedy’s public demeanor and perhaps hoped her son, William, would inherit similar traits. In a conversation just weeks before her death, she expressed a wish for William to be as smart as him.

Another motivation behind Diana’s willingness to meet could have been to provoke a bit of jealousy in her sister-in-law, Sarah Ferguson, as Kennedy was regarded as quite the catch at that time.

It’s worth noting that Kennedy’s allure extended beyond Diana. Just a month ago, Madonna referred to him as her “best down” in a conversation, reminiscent of their brief romances back in the ’80s.

Although Kennedy’s encounter with Diana wasn’t romantic, he did go on to marry Carolyn Bessette in 1996. Their relationship, characterized by ups and downs, was recently highlighted in FX’s *Love Story*, which debuted in February. Tragically, both lost their lives in a plane crash in 1999.

A former friend described Kennedy’s fleeting romance with Diana as “a total fling,” emphasizing it was nothing significant—just a brief moment.