Princess Diana ‘Didn’t Comment’ on JFK Jr.’s Looks After They Secretly Met, but He Did

Imagine two of the most famous people in the world being together in the same room and the public being none the wiser. That’s what happened when Princess Diana and John F. Kennedy Jr. secretly met in 1995. Ahead, what JFK Jr. said about the British royal’s looks . Plus, why Diana didn’t comment on his.

Diana and JFK Jr. had a ‘discreet’ meeting about George magazine

In JFK Jr.: An Intimate Oral Biography , JFK Jr.’s former executive assistant RoseMarie Terenzio and co-author Liz McNeil shared details of a secret meeting between JFK Jr. and Diana.

The two met in New York, New York, in the summer of 1995 after Kennedy wrote to the British royal asking if she’d be on the cover of his new George magazine. The hope? To get Diana to dress up as an American historical figure. (Cindy Crawford previously dressed as George Washington for the inaugural issue.)

Diana responded to his letter, suggesting they meet in person to discuss the proposal. Her private secretary, Patrick Jephson, worked out the details with Terenzio, settling on a weekday afternoon meeting at the Carlyle Hotel, where Diana was staying.

“It was never made public, so that made it quite fun, actually,” Jephson said. “Diana wanted it to be discreet because it had all the makings of a great gossip story, didn’t it? World’s most eligible bachelor, wasn’t he at the time? And she had just got unmarried or was in the process of getting unmarried. It would’ve been a rather intriguing thing to dream about.”

JFK. Jr. wasn’t actually a bachelor when they met. He was dating Carolyn Bessette. The two would go on to become engaged in the summer of 1995 before marrying on Sept. 21, 1996.

Meanwhile, Diana had been separated from her husband, the now- King Charles III , since 1992. Their split wouldn’t become official until August 1997, shortly before her death in a Paris, France, car accident .

Diana’s height surprised an awestruck John F. Kennedy Jr.

Now for JFK Jr.’s comments about Diana’s appearance. He later told Terenzio: “She’s much taller than I thought—and she’s got great legs.” Diana stood at 5’10’’ as an adult, and in 1980, a photo of her posing in a skirt with her legs backlit by the sun quickly became famous.

JFK Jr. “was quite in awe of her,” Jephson recalled. “Not uncomfortable, but he certainly seemed to be on his best behavior. He rather sat on the edge of his chair and looked nervously at her.”

As for Diana, she “was not nervous at all to meet him,” he added. “She was very cool—and jolly, you know, and smiley and welcoming.”

Diana saw him as ‘vulnerable’ for growing up in the public eye

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Meanwhile, Diana “didn’t comment on his looks,” Jephson said. “She was used to being judged by her looks, and therefore didn’t have much time for it.”

He explained that Diana saw beyond JFK Jr.’s physical attributes to his life in the spotlight as the son of President John F. Kennedy and former First Lady Jacqueline Kennedy Onassis.

“She didn’t see him as the rest of the world saw him—as this big, famous, handsome guy,” Jephson said. “She saw him, I think, as rather vulnerable because he had grown up in public.”

Ultimately, Diana declined the offer to be on the cover of the magazine. She died less than two years later. JFK Jr. and Bessette Kennedy, along with Lauren Bessette, died in a 1999 plane crash.