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Men Princess Diana had affairs with during marriage

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Updated on June 17, 2023

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As the late Princess of Wales Diana graces the cover of Tatler on what would have been her 60th birthday, we look back at the boyfriends, flames, and frissons that were either a part of or reported to be a part of her life, as she was never short of fans. She was iridescent, usually wonderfully dressed, and had a bright sense of fun to match. As shown in The Crown, Diana’s young charm and appropriateness for her role as Princess of Wales (and admission into the Royal Family) was largely due to the absence of controversy and shady connections in her wake. It’s usually assumed that the Prince of Wales was Diana’s first formal lover – which isn’t unexpected considering that Diana was 19 at the time their engagement was announced.

On July 29, 1981, Princess Diana married Prince Charles in a grandiose ceremony in front of the world — but the pair soon began seeing other people. Their romance ended in 1996, and Diana famously claimed that when it came to Prince Charles and Camilla Parker-Bowles, there were “three people in the marriage.”

Rumours arose around the palace of an affair between the Princess and Barry Albert Mannakee, who was a police officer with the Royal Protection Squad before being deployed as Princess Diana’s bodyguard in 1985. This resulted in his removal from the position a year later. He was killed in a motorbike accident in 1987, sparking conspiracy rumors that his death was pre-planned. Diana fuelled these claims in a video later discovered by NBC, in which she said, “I was only happy when he was around,” and described his death as “the biggest blow of my life.” ‘I think he was bumped off, but there we are,’ she added. When she spoke about a guy she was in love with on the secret tapes, he was never identified by name, but it was presumed she was speaking to him. She stated on the tapes that she was “deeply in love” with the unnamed security officer and was “quite happy to give all this up and just go off and live with him.” The death of Mannakee was reinvestigated as part of the Diana probe, as part of Operation Paget, which was headed by Sir John Stevens.

Then there’s Major James Hewitt in The Crown, played by Russian actor Daniel Donskoy. According to Hewitt’s confession in the tumultuous book Princess in Love, his affair with the princess lasted from 1986 until 1991. (From 1981 until 1996, she was married to Charles.) Tina Brown writes in The Diana Chronicles, “For five years he was as available and attentive as a medieval troubadour,” However, Hewitt only appears briefly in The Crown.

By 1989, Princess was also said to be dating James Gilbey, the heir to a gin fortune. Diana has known them since she was a youngster. She has always denied the affair, and the former Lotus car executive has never talked about it, but he has claimed a place in royal history as the person on the other end of the line during the infamous ‘Squidgygate’ phone call in 1989. (that was recorded). In it, he referred to the Princess as ‘Squidge’ or ‘Squidgy’ 53 times and described putting his arms around her and holding her tight. The existence of the tapes was disclosed in 1992 by The Sun, in which the Princess purportedly claimed that her husband, Prince Charles, ‘makes my life real, real torture’.

Oliver Hoare was likewise followed by the princes. Diana began an affair with art dealer Oliver Hoare in 1992, according to The Mirror. In case you’re wondering, Charles and Diana announced their divorce in December 1992. When the alleged romance began, the Princess of Wales had known Hoare for quite some time since he was good friends with her husband. Diana had an affair with Hoare, according to The Sun, shortly after her father, Earl Spencer, died in March 1992. Hoare was 16 years her senior, and the affair supposedly ended when his wife threatened to divorce him unless he halted his relationship with Diana.

In 1995, the princess fell in love with England rugby great Will Carling, whom she met during an early-morning exercise at London’s Chelsea Harbour Club. She admired him and requested private training sessions, and the pair apparently had two trysts, but he denies this. Their romance was blamed for his divorce with TV personality Julia Carling the following year. Will was newly married when he met Diana, and his then-wife Julia is alleged to have publicly warned her off. Will now owns a corporate hospitality firm with his second wife Lisa and has two children.

In 1997, the princess also adored Dodi Al Fayed, the oldest son of former Harrods owner and billionaire Mohamed Al Fayed. Dodi was a Playboy who was associated to a slew of renowned ladies, including Winona Ryder and Nancy Sinatra. He first met Princess Diana during a polo match in Windsor in 1986, when she was still married to Prince Charles, but nothing came of the encounter.

Dodi asked Diana, William, and Harry to spend time aboard his boat in the south of France in the summer of 1997. She eventually returned to the ship without her sons in August, and a photo of the two kissing made headlines across the world. Before travelling to Paris, the pair spent time in the south of France and Sardinia.

On August 31, 1997, after dinner at Mohamed Al Fayed’s Ritz hotel in Paris, the duo were pursued by motorbike-riding French photographers. They were driving through the Pont de l’Alma tunnel when they collided with a pillar and died at the scene.