The Real Story Behind Prince Charles and Princess Diana’s Romances and Affairs

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The general public is significantly more aware of the romantic relationships inside the royal family as a result of five seasons of The Crown. While Camilla Parker Bowles and Prince Charles’ courtship was the focus of Season 3 of the royal Netflix series, Season 4 focused heavily on the ups and downs of the Prince and Princess of Wales’ marriage, including the extramarital relationships both royals had. The last episode of Season 5, which debuted on Netflix, will examine how those alleged encounters affected Charles and Diana, both positively and negatively.

Here is the facts you need to know about the romantic partners with both Prince Charles and Princess Diana.

BARRY MANNAKEE

Diana’s connection with her bodyguard was only passingly made fun of by Princess Anne in Season 4 of The Crown, played by Erin Doherty. Barry Mannakee, however, appears to have played a significant role in Diana’s life in real life.

Diana discussed her feelings for Mannakee in private recordings with her vocal coach, Peter Settelen, according to OprahMag.com. The princess referred to the bodyguard on the audio, which were made public after Diana’s passing, as her “greatest love” of all time. She would have been, in Diana’s opinion, “quite happy to give all this up and to just go off and live with him. And he kept saying he thought it was a good idea too.”

She didn’t specifically mention Mannakee in the tapes, but he’s the most plausible candidate given that she said that Mannakee was her “greatest love,” and that he tragically died in a motorcycle accident in 1987. The Associated Press reports that Diana stated on the Settelen tapes that she thought Mannakee’s demise was preplanned. “It was all found out and he was chucked out. And then he was killed,” said the princess.

“And I think he was bumped off. … We’ll never know. He was [the] greatest fella I’ve ever had.” She also said of him, “I was only happy when he was around. … I was like a little girl in front of him the whole time.”

JAMES HEWITT

The Crown Season 4 also made reference to Diana and James Hewitt’s relationship. It appears that Diana’s romance with Mannakee came to an end after she started seeing the cavalry commander. Hewitt revealed that his relationship with the princess lasted from 1986 until 1991, as per Anna Pasternak’s book Princess in Love (reported on by OprahMag.com). Also according to the BBC, Lady Diana “stopped taking Hewitt’s phone calls” in 1992.

In his 1999 book Love and War, Hewitt said that the Princess of Wales asked him to teach her how to ride, which is how the relationship began. According to him  “Only one thing went wrong,” he revealed. “We fell in love.”

Pasternak wrote this in a piece for The Daily Mail: “Hewitt was regularly bundled into car boots and driven to Kensington Palace when their affair ensued. He told me he was terrified the first night he stayed in Kensington Palace, relieved at least that Charles and Diana had separate bedrooms. Apparently, she had 30 childhood cuddly toys lining the end of her bed.”

The princess spoke about her relationship with Hewitt and his part in the writing of the autobiographical book Princess in Love in a 1995 interview with BBC’s Panorama. “Yes, I adored him,” Diana said. “Yes, I was in love with him. But I was very let down.”

JAMES GILBEY

During her turbulent marriage to Charles, Diana allegedly frequently went to her old friend James Gilbey for support. Gilbey and Diana supposedly reconnected in the late 1980s and found themselves at the center of a storm after a recording of one of their phone conversations was released according to Honey. Gilbey was described as “the heir to a considerable gin fortune.”

The conversation, which was recorded, featured the two talking about New Year’s Eve in 1989. It became known as “Squidgygate” because of the nickname Gilbey called Diana throughout the conversation. According to Honey, what had appeared to be a casual conversation turned into something more personal when Gilbey suggested that he was “playing with himself” and requested a kiss from Diana. Gilbey, though, is said to have insisted that his friendship with Diana was all that it was.

OLIVER HOARE

Diana allegedly started an affair with art dealer Oliver Hoare in 1992, according to The Mirror. As a point of perspective, Diana and Charles separated in December 1992. Hoare had been a close friend of the Princess of Wales’ husband for a long time before the alleged affair started.

Soon after her father Earl Spencer passed away in March 1992, according to The Sun, Diana started dating Hoare. The relationship apparently came to an end when Hoare’s wife threatened to file for divorce unless he stopped dating Diana, despite the fact that he was 16 years her senior.

CAMILLA PARKER BOWLES

Prince Charles and Camilla Parker Bowles began dating in the early 1970s and stayed close even after they both married other people. People claims that the ex-couple renewed their intimate contact while still married in 1986.

A tape recording of an inappropriate phone call between the two that occurred in 1989 was leaked in the early part of 1993, causing a scandal for the royal family and confirming the couple’s affair. Diana made the infamous comment in an interview on BBC One’s Panorama in 1995: “There were three of us in this marriage, so it was a bit crowded.”

Charles and Diana divorced in August 1996, while Camilla filed for divorce in January 1995.

BARBRA STREISAND

Although the prince has been associated with numerous women throughout the course of his life, the majority of these relationships allegedly began before he wed Diana. The book Game of Crowns: Elizabeth, Camilla, Kate, and the Throne, as observed by Town & Country, asserted that Charles had a significant infatuation on Barbra Streisand and that something amorous may have taken place between the unusual pair. After meeting Streisand on the Funny Girl set in 1974, author Christopher Andersen told Inside Edition “Twenty years later, he is back in Los Angeles, and nobody is aware of their covert meeting at the Bel Air Hotel. Diana was fully aware of what was happening.” It’s unclear, though, if this specific story is true or not.