From her incredible looks to her humanitarian efforts, the world has been mesmerized by Princess Diana since even before her wedding to King Charles III in 1981. But, speaking of her wedding to Charles, it’s no secret their marriage was less than ideal, with the two fizzling out and at odds with one another since the very beginning.
So, much like Charles’ longtime extra-marital affair with the now Queen Camilla, Diana also lived some affairs throughout the years to get by. From her highly-publicized five-year relationship with James Hewitt to her short-lived affair with British rugby star Will Carling, Diana didn’t let her estranged marriage stop her from falling in love and going through her fair share of heartbreaks over the years.
To find out all of the men the late Princess of Wales once had a relationship with, from her affairs during her marriage to Charles and beyond, scroll below!
King Charles III
Of course, we can’t talk about Diana’s dating history without starting with her marriage to King Charles III. The two met in 1977, started dating in 1980 and tied the knot in a lavish worldwide occasion on 29 July 1981. And, as most of us already know, their marriage went downhill fast given Charles’ longtime affair with his now-wife Queen Camilla.
Diana and Charles, who shared kids Prince William and Prince Harry, announced their separation in 1992 and were officially divorced four years later in 1996.
Barry Mannakee
In 1985, Sergeant Barry Mannakee was hired as Diana’s newest bodyguard. Soon after, their connection blossomed from professional to romantic. “I was only happy when he was around,” Diana said in private tapes recorded by her voice coach Peter Settelen, per Oprah Daily. “I was like a little girl in front of him the whole time.”
Sadly, in 1987, Mannakee was killed in a motorcycle crash. Understandably, the news rocked the royal. “This was the biggest blow of my life,” Diana said of his death, per the tapes. “I just sat there all day going through this huge high profile visit to Cannes, thousands of press, just devastated. Because, you know, I wasn’t supposed to mind as much as I did, if you know what I mean.”
James Hewitt
Probably one of the most-known of Diana’s affairs was her romance with former Household Cavalry officer James Hewitt. The two began their relationship in 1986 and dated until he left to serve in the Gulf War in 1991.
In 1994, Hewitt made his romance with Diana public when he cooperated with author Anna Pasternak for the book Princess in Love, per Town & Country. A year later, during Diana’s iconic Panorama interview, she confirmed it. “Yes, I adored him,” the royal said. “Yes, I was in love with him, but I was very let down.”
Oliver Hoare
Although art dealer Oliver Hoare never confessed to his affair with Diana, the royal’s former royal protection officer Ken Wharfe opened up about their extra-marital relationship to The Sun in 2018.
“She confided to me that he was the first man who had ever aroused her physically,” Wharfe remembered, adding that Diana was “completely in love” with him. Their affair reportedly ended when their dalliances became too obvious to ignore and both Charles and Hoarse’s wife, French oil heiress Diane de Waldner, found out about their rendezvous.
Will Carling
Former British rugby star Will Carling also lived a short relationship with Diana. In 1995, Will’s wife Julia confirmed their relationship and even shaded the former Princess of Wales.
“This has happened to her before, and you hope she won’t do these things again, but she obviously does,” Julia told Daily Mail, per Buffalo News. “She picked the wrong couple to do it with this time because we can only get stronger from it. I am sad that Will put himself in that position and that the princess did as well.”
Bryan Adams
Singer Bryan Adams has long been rumored to have had an affair with Diana. During an episode of Watch What Happens Live five years ago, Adams attempted to squash the rumors saying they were just “good friends.” As to how they would meet, Adams said, “She didn’t sneak me in, I would just roll up.”
James Gilbey
Ever heard of Squidgygate? If not, here’s everything you need to know: On New Year’s Eve in 1989, a phone call between Diana and Lotus executive James Gilbey was taped, and later broadcast to the world. During the call, Gilbey calls Diana “darling” a whopping 53 times and “Squidgy” 14 times.
In the 23-minute call, Diana can be seen venting about the “torture” of royal life and the two have some flirty exchanges. “Do you know what I’m going to be imagining I’m doing tonight, at about 12 o’clock? Just holding you close to me,” Gilbey said to Diana on the call. Gilbey has since denied their affair though many sources throughout the years have confirmed it.
Hasnat Khan
For many, Hasnat Khan, the Pakistani heart surgeon Diana dated from 1995 to 1997, was the “love of her life.”
In a statement to the Police, obtained by Express, Khan opened up about their two-year relationship. “Diana and I had a very good relationship with no personal problems,” he said. “The only problem we did have was with the media and the only place we could have any real privacy was at Kensington Palace. Diana was very protective towards me and wanted to shield me from the attention.” Ultimately, the stress of being in the limelight proved too much for Khan and he broke things off with the royal.
Dodi Al Fayed
After her split with Khan, Diana joined a friend and former Harrods owner Mohamed Al Fayed and his family on a trip on his yacht in the south of France. While on the trip, photos of her kissing Mohammed’s son Dodi hit the headlines.
The two then continued their jet-setting romance and visited the South of France and Sardinia before flying to Paris. On 31 August 1997, both Diana and Dodi died in a fatal car crash in Paris’ Pont de l’Alma tunnel.
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