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Details About Princess Diana’s Alleged Affairs That ‘The Crown’ Brought To Light

Updated December 18, 2020 50.5k views13 items
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It's taken four seasons, but Netflix's The Crown has finally reached the Princess Diana years. Diana Spencer, Princess of Wales, has fascinated the world ever since her engagement to Prince Charles was announced in 1981. Almost immediately after she was first introduced, she eclipsed her husband's fame and became the most photographed woman in the world. Her fans loved her for her humanitarian work and her impeccable sense of style. But they loved her even more because of her sympathetic personal life. 

Diana and Charles's relationship was never a happy one. Charles never fully got over his relationship with his ex, Camilla Parker Bowles, which cast a pall over their entire marriage. Charles carried on an emotional affair with Camilla throughout his marriage with Diana, and it crossed over into a physical affair in 1985 (if not earlier). Meanwhile, Diana struggled with both a loveless marriage as well as her sudden, unwanted celebrity status. Since Charles didn't respect their marriage vows, Diana began having affairs of her own. 

James Hewitt is probably the best known of Diana's lovers, but he was by no means the only one. Here are all the details about the other men in Princess Diana's life. 

  • Charles Allegedly Approved Of Her Liaison With Hewitt

    As you might imagine, it's difficult to keep your flings on the down-low when you're one of the most famous people in the world. It's even more difficult because the royals are almost always surrounded by household staff. That makes secrecy nearly impossible. Just like Diana was aware of Charles's relationship with Camilla, Charles was probably aware of Diana's relationships with other men. 

    In their 12-part biography of Diana originally published in the Daily Mail, Richard Kay and Geoffrey Levy claim that Charles didn't care that Diana was cheating on him, since he'd already resumed seeing Camilla.

    One photograph taken after the affair began captured Charles, Diana, and James Hewitt at a party. They appear to be laughing together and enjoying themselves. 

  • Staffers Snuck Hewitt Past Security By Hiding Him Under a Blanket In The Back Seat Of A Car

    Diana's next bodyguard after Barry Mannakee was Ken Wharfe. They developed a close friendship, and Wharfe didn't judge Diana for her extramarital liaisons. In his memoirs, Wharfe describes how he even helped facilitate them. 

    When James Hewitt visited Diana on weekends at Highgrove Estate, Diana's butler Paul Burrell would pick him up in a car and hide him in the back seat under a blanket. When Highgrove wasn't available, Diana and James would meet up at Sheiling Cottage in Devon, owned by Hewitt's mother Shirley. Diana and Shirley were apparently close. 

    Occasionally, Diana used code names to avoid scrutiny. When she would call Shirley to let her know she was coming to Sheiling, she called herself "Julia" and talked in a cockney accent. 

  • Hewitt's Military Career Led To Their Breakup

    Sources differ on exactly when Diana and James Hewitt ended things, but it was most likely due to his commitment to his military career. According to Ken Wharfe, Diana ended the relationship in 1989 when Hewitt accepted a four-year posting in Germany and waited until the last possible moment to tell her. 

    But Diana apparently wrote to Hewitt while he was stationed in Iraq during the Persian Gulf War. Hewitt was discharged from the military in 1991, and he later claimed it was because of his rumored relationship with Diana. Shortly after his discharge, Diana stopped responding to his calls. 

  • Diana May Have Had A Fling With Childhood Friend And Car Dealer James Gilbey

    At some point in 1989, Diana may have gotten together with James Gilbey, heir to a gin fortune and owner of a Lotus dealership. They had known each other most of their lives. A decade earlier, friends tried to set them up on a date, but James stood Diana up. Diana and a roommate apparently floured and egged his Alfa Romeo for revenge. 

    Diana and Gilbey reconnected in the late 1980s, as Diana's marriage with Charles was falling apart. Diana and Gilbey claimed they were just close friends, but this was the same explanation she had offered for her relationship with Hewitt. Andrew Morton called it a "dalliance," while Tina Brown considered it a full-blown affair. 

    Gilbey still hasn't spoken publicly about his relationship with Diana. While it may not have been physical, Diana and Gilbey's relationship caused a media firestorm when it came to light three years later.