Why Princess Diana's Meeting With Oprah Winfrey "Became a Friendly Tug-of-War," According to Former Butler

"Oprah kept returning to it to embarrass me."

Oprah Winfrey wears a bright red dress, and opposite, Princess Diana is wearing a blue Catherine Walker outfit at Bayan Palace in Bayan, Kuwait, 13th March 1989
(Image credit: Ron Galella/Ron Galella Collection via Getty Images/Tim Graham Photo Library via Getty Images)

Throughout her life, Princess Diana was well-known around the globe. As a result, it's entirely unsurprising that she reportedly had a private meeting with talk show legend Oprah Winfrey, which led to a "friendly tug-of-war."

In his book A Royal Duty, former royal butler Paul Burrell opened up about Princess Diana's meeting with Oprah Winfrey.

Burrell shared in his book, "The princess was really nervous about meeting [Winfrey] because, she said, 'She is such a big name.' It didn't cross her mind that perhaps Oprah would be nervous too."

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According to the former butler, Diana "made her typical confident entrance" to meet Winfrey. "'Sorry to keep you waiting, sorry, sorry,' [Diana] said," Burrell recalled. "I served lunch in the dining room and soon became part of the proceedings as conversation turned to America."

Sharing the private conversation, Burrell explained, "We love America, don't we, Paul?' the princess said. 'He goes there every year for a holiday.' Cue Oprah to the princess: 'So, would you ever consider living in the United States?'"

Princess Diana wearing a purple dress and pearls waving to a crowd in 1996

Princess Diana reportedly had a private meeting with Oprah Winfrey.

(Image credit: Getty Images)

According to Burrell, he pitched in with a joke: "I would pack my bags and go and live in America tomorrow."

The butler continued, "I looked at the princess and winked. Oprah saw her opportunity. 'We could do with a butler. Why don't you come to Chicago and look after me?'"

As documented in his book, Burrell recalled Princess Diana bristling at the thought of Winfrey poaching her royal butler.

"The princess suddenly straightened in her chair," Burrell wrote. "'Look, Oprah,' she said, laughing, 'he's my butler and he's staying here.'"

Per Burrell, "It became a friendly tug-of-war all the way through to coffee: Oprah kept returning to it to embarrass me."

Oprah Winfrey is seen at "Jimmy Kimmel Live" on September 17, 2024 in Los Angeles, California wearing chloe sneakers and a denim jumpsuit

"It became a friendly tug-of-war all the way through to coffee: Oprah kept returning to it to embarrass me."

(Image credit: Getty Images)

The joke apparently continued right up until the moment Winfrey left Kensington Palace.

"Just before she pulled away, Oprah opened the window, leaned forward and said: 'This is your last chance, Paul,'" Burrell shared. "The Boss stood beside me at the front step, threw a possessive arm round me and shouted out: 'Hey, he's mine—and he's staying here with me.'"

Luckily, the meeting reportedly ended in "laughter." Basically, Princess Diana and Oprah Winfrey appeared to develop quite the rapport during their alleged meeting.

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Amy Mackelden
Weekend Editor

Amy Mackelden is the weekend editor at Marie Claire, where she covers celebrity and royal family news. She was the weekend editor at Harper’s BAZAAR for three years, where she covered breaking celebrity and entertainment news, royal stories, fashion, beauty, and politics. Prior to that, she spent a year as the joint weekend editor for Marie Claire, ELLE, and Harper's BAZAAR, and two years as an entertainment writer at Bustle. Her additional bylines include Cosmopolitan, People, The Independent, HelloGiggles, Biography, Shondaland, Best Products, New Statesman, Heat, and The Guardian. Her work has been syndicated by publications including Town & Country, Good Housekeeping, Esquire, Delish, Oprah Daily, Country Living, and Women's Health. Her celebrity interviews include Jennifer Aniston, Jessica Chastain, the cast of Selling Sunset, Emma Thompson, Jessica Alba, and Penn Badgley. In 2015, she delivered an academic paper at Kimposium, the world's first Kardashian conference.