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‘Naked Underneath and Wearing Lots of Jewels’—Princess Diana’s Confidante Recalls How She Showed Up to a Married Man’s House

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Published On: July 13, 2025
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Princess Diana had several alleged affairs after her divorce from Prince Charles. One affair out of all especially stood out, which was with a married art dealer. A royal biographer even claimed that Diana once showed up at the man’s house in nothing but a tiara and fur coat.

The man with the late royal allegedly had an affair with was named Oliver Hoare. Diana and the man were alleged to have an “incredibly close bond.” Royal biographer Sally Bedell Smith reports that Lady Elsa Bowker gave her an insight into the late royal’s relationship with the art dealer.

Lady Elsa Bowker was like a “mother figure” to Diana at the time. The princess was 32 years old when her affair with the 46-year-old started. Hoare was an art dealer and a close friend of Prince Charles at the time.

Oliver Hoare was already married to Diane de Waldner de Freundstein and shared three children from their marriage. Diane de Waldner de Freundstein was the heiress of a wealthy French family. Lady Elsa reportedly got close to Diana over the span of the affair.

Diana often shared the details of her affair with Lady Bowker. “Once when Oliver’s wife was out of town, he told Diana he had to leave because he had to see his daughter, who had a fever,” the Lady claimed.

Lady Elsa recalled how suspicious Diana was of Hoare, she was also extremely “suspicious and mistrustful” of him. Bowker claims that Diana even threatened to jump out of a moving car because of how upset she was. When the car stopped at Sloane Square, Diana got out of the car.

“Suddenly Diana did jump out, leaving behind her bag and her money and everything,” Bedell Smith writes in her book Diana In Search of Herself. This incident left Oliver shaken enough that he was “distraught” as a result. The art dealer then drove around the city for hours only to find the princess at a park near Kensington Palace, where she was “lying down and weeping.”

Lady Elsa detailed how the pair’s affair was mainly a sexual one. She shared how Diana went to Hoare’s family home in a fur coat and a tiara. The art dealer’s wife and children were out of town at the time. “Underneath, she was naked and wearing lots of jewels. Both Diana and Oliver told me that” the lady shared.

The Princess reportedly wasn’t too pleased when she learned that Hoare wasn’t too keen on leaving his wife and children for her. She allegedly continuously called up his Chelsea home after learning the news.

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Vaishnavi Shetye

Vaishnavi has been a content writer for over four years and firmly believes there’s no such thing as too many pop culture references. She was a publishing student and is a full-time reader. You’ll find her at parties handing out great (self-proclaimed) books, movies, and series recommendations. She also takes pride in consuming media content as Pac-Man devours dots—swiftly and perpetually.

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