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    1. Celebrity
    2. Royals

    Princess Diana Asked an Unlikely American Celebrity for Parenting Advice About William and Harry

    The late royal was visiting Chicago in 1996 when she had a "really lovely" conversation at a charity lunch.

    Kristin Contino#039;s avatar
    By Kristin Contino
    Published 3 October 2026 In News

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    Princess Diana wearing a white suit and hat smiling at Prince Harry and Prince William, who are looking at a program
    (Image credit: Getty Images)
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    Charles Spencer has been busy promoting his new book, Swan Song: Diana, My Sister, in the United States this week, and on the latest episode of the “Next Question With Katie Couric” podcast, Couric told Earl Spencer about one of her personal encounters with Princess Diana.

    While attending a charity luncheon for breast cancer research held in Chicago in 1996, the journalist found herself sitting “two seats away” from Diana. “She complimented my lipstick. I was very flattered,” Couric recalled.

    The broadcaster shared how she remembered Diana being “really lovely and easy to talk to,” and said the royal even asked her for some parenting advice.

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    Princess Diana wearing a purple gown

    Princess Diana attends a gala during her visit to Chicago in 1996.

    (Image credit: Getty Images)

    Couric, who had two very young daughters at the time, recalled Diana “was asking how to keep William and Harry from watching too much telly, because I think they were young teenagers.”

    The boys, who were 11 and 13 at the time, were splitting their time between their mother and Prince Charles, whose divorce would be finalized later that summer. The former Today show host said she remembered the sad response Diana gave when asked about returning home to London.

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    “I said, ‘This must be exhausting, you know, traveling all over the country.’ I don’t know how many cities she was going to, but you know, just exhausting, shaking hands, making small talk, meeting person after person after person,” Couric told Earl Spencer.

    “I said, ‘You must be so excited to go home.' And she kind of looked at me and said, ‘Yes, but I’ll be going home to an empty house,’” Couric shared.

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    Princess Diana visiting Chicago wearing a white dress and pearls

    Princess Diana visits Chicago in 1996.

    (Image credit: Getty Images)

    Earl Spencer admitted that he didn't realize how unhappy his sister was after her separation from Prince Charles, telling Couric, “I regret to say I was probably just so busy getting on with my own life. And I think Diana spoke more about her marital problems to our mother and sisters than to the younger brother."

    “It was amazing she coped as well as she did, given the huge amount of pressure on her," Spencer said. "Unprecedented pressure.”

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    Diana Prince Harry Prince William
    Kristin Contino
    Kristin Contino
    Senior Royal and Celebrity Editor

    Kristin Contino is Marie Claire's Senior Royal and Celebrity editor. She's been covering royalty since 2018—including major moments such as the Platinum Jubilee, Queen Elizabeth II’s death and King Charles III's coronation—and places a particular focus on the British Royal Family's style and what it means.

    Prior to working at Marie Claire, she wrote about celebrity and royal fashion at Page Six Style and covered royalty from around the world as chief reporter at Royal Central. Kristin has provided expert commentary for outlets including the BBC, Sky News, US Weekly, the Today Show and many others.

    Kristin is also the published author of two novels, “The Legacy of Us” and “A House Full of Windsor.” She's passionate about travel, history, horses, and learning everything she can about her favorite city in the world, London.

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