Given the world’s ongoing obsession with Princess Diana, it’ll come as no surprise that the princess had no issues finding a range of suitors who were keen to whisk her away from the royal life she so famously struggled with. Some of these lovers came into her life while she was still married to Charles and some before they had even officially separated. As we know, Charles himself was no stranger to extramarital affairs, with his ongoing relationship with Camilla Parker Bowles causing much stress and strain on his marriage to Diana.
Despite all the drama, Lady Di kept an air of grace and dignity which drew in admirers from all over the world, but none fascinated her more than the men in her inner orbit. Some of them have never been officially confirmed and likely never will be, but there’s enough buzz around them for people to believe something went down at some point.
Below, everything you need to know about Princess Diana’s lovers over the years, from 1981 to 1997.
Prince Charles, 1981-1992
It’s widely believed that the Prince of Wales was Diana’s first proper boyfriend which isn’t too surprising given she was just 19 when they got engaged.
Even though they didn’t officially split until 1992, Diana was rumoured to have engaged in extra-marital affairs before that, likely because Charles had been doing the same.
“There were three of us in this marriage, so it was a bit crowded,” Diana famously told the BBC in 1995. She was of course, referring to Charles’ long-time lover, Camilla Parker Bowles, whom he resumed seeing once they had separated. Eight years after Diana’s death, Charles and Camilla announced their engagement 35 years after they first met.
Barry Albert Mannakee, 1985
Mannakee was employed as Diana’s bodyguard in 1985 but was dismissed just one year later after rumours began circling of an affair between the two. In 1987 he was killed in a motorcycle accident which was said to have upset Diana deeply.
In private tapes recorded with Diana’s voice coach, Peter Settelen and released after her death, Diana spoke of Mannakee without naming him, saying: “I was only happy when he was around,” and that she would have been “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.”
In the same tape, she described his death as, “the biggest blow of my life,” before insinuating that his death had not been caused by a freak accident.
“I think he was bumped off, but there we are,” she said.
James Hewitt, 1986-1991
Diana and James embarked on a years long affair which began in 1986 when they met at a cocktail party. He then became Diana’s riding instructor after she confessed her fear of horses, with their relationship allegedly taking place at the same time Charles was cheating with Camilla.
“Hewitt, a natural womaniser, gave her the attention and affection she relished, and then the passion she yearned for,” wrote Ken Wharfe, her former protection officer, in Diana: Closely Guarded Secret. “The pair usually met at an old cottage in Devon belonging to Shirley, Hewitt’s mother, where the creaking bedroom floorboards told the story more loudly than any confession.”
By the end of the 1980s, Hewitt was deployed to serve in the Gulf War, which apparently left Diana furious that he had chosen his career over her. Though they stayed in contact initially after he was stationed in Saudi Arabia in 1990, the relationship was apparently over.
In 1994, Hewitt cooperated with author Anna Pasternak for the book Princess in Love, which detailed their extramarital affair. Due to the level of scandal, it became a best-selling sensation.
“Yes, I adored him. Yes, I was in love with him. But I was very let down,” Diana told BBC’s Panorama in 1995, of Hewitt’s involvement in the publication of the tell-all book.
James Gilbey, 1989
Synonymous with ‘Squidgygate,’ James was a longtime childhood friend of Diana’s who may have been something more. When a leaked transcript of a phone call between the two emerged in 1989, suspicions rose that something else was going on when James called Diana a pet name, ‘squidgy’, a total of 53 times.
During the conversation, Diana speaks about her fear of getting pregnant, though it’s not clear to whom.
DIANA: “I don’t want to get pregnant.”
GILBEY: “Darling, that’s not going happen, all right? Don’t think like that. It’s not going to happen, Darling; you won’t get pregnant.”
Later in the call, the pair imitate kissing and speak of a certain ‘feeling,’ they haven’t experienced in a while.
GILBEY: [sighing] “Squidgey, kiss me [sounds of kissing by him and her]. Oh, God, it’s wonderful, isn’t it, this sort of feeling. Don’t you like it?”
DIANA: “I love it!!”
GILBEY: “Isn’t it absolutely wonderful?!? I haven’t had it for years. I feel about 21 again!”
DIANA: “Well, you’re not. You’re 33.”
In the same conversation, Diana speaks of her gripes with Charles and how he “makes my life real, real torture,” speaking to their marital difficulties at the time. Despite the rumours, Diana always denied the affair but the transcript was considered damning enough for people to speculate otherwise.
Oliver Hoare, 1992-1994
In the early nineties, Diana struck up a relationship with an Islamic art dealer who was 16 years her senior. Oliver was actually a friend of Charles’ and can be seen standing behind him in the above photo. Oliver and his wife, Diane de Waldner de Freundstein would often stay in Windsor castle, but after beginning his extramarital affair with Diana, began entering the castle via more secretive methods.
One night, he was found by a policeman hiding behind a potted tree smoking a cigar after the fire alarm sounded at Kensington Palace where Diana had her apartment, and another night he was said to have been seen entering Kensington Palace via the boot of Diana’s car.
The affair came to an end after Oliver refused to leave his wife, with some claiming Diana became a little over infatuated when she allegedly rang his home 300 times in one night.
In Diana’s Panorama interview in 1995, she admitted calling Hoare over a period of six to nine months, but remained adamant that it was, “certainly not in an obsessive manner”.
Will Carling, 1995
During an early-morning workout at London’s Chelsea Harbour Club in 1995, Diana met former England rugby star Will Carling, who was married to TV presenter Julia Carling at the time. After their meeting, Diana reportedly asked for private training sessions which lead to a fleeting romance.
When it was publicly revealed that Will had visited the Princess at Kensington Palace, as proven by his tell-tale blue Range Rover spotted in the car park, Julia publicly fired a warning shot at Diana, declaring that she had “picked the wrong couple”.
“It would be easy to say she’s ruined my marriage, but it takes two to tango and I blame Will for getting involved in the first place,” she said, just a year before they divorced.
Will adamantly denied the rumours, but in 2021 made comments about “behaving stupidly” which sparked speculation that he was confessing.
“It was a bit of a mess,” he told the Eden Confidential.
“Just making messes of relationships because you’re sort of rudderless and you’ve lost your focus and you don’t behave well, and I didn’t. Never intentionally or vindictively, I just think that was me, I just was in a bit of a mess.”
Hasnat Khan, 1995-1997
Described by Diana as ‘Mr Wonderful’, British-Pakistani heart and lung surgeon Khan was thought by friends to have been the ‘love of Diana’s life’. The pair met in 1995 at the Royal Brompton Hospital in London where Khan worked. Diana was visiting a close friend who was recovering from heart surgery and felt a spark with the surgeon almost immediately.
According to Reader’s Digest, the couple would often meet at the hospital, spending nights together in a “small, overnight room” and seeking more private time at Kensington Palace.
In a bid to immerse herself in his native culture, Diana filled her wardrobe with colourful silk tunics and trousers, made numerous trips to Pakistan and reportedly considered converting to Islam.
While their relationship began before Charles and Diana’s divorce had been finalised, Khan reportedly refused to consummate things until afterward.
In his inquest statement, Khan revealed that it was Diana who called their relationship off, shortly after she met Mohamed Al Fayed in July 1997. While he said “she denied there was anyone else involved,” he maintained that he had “strongly suspected there was someone else.”
While she may have initiated their split, Khan revealed that he found the public intrusiveness difficult to deal with.
“My main concern was about us getting married was that my life would be hell because of who she was,” he said, during the inquest. “I knew I would not be able to live a normal life and if we ever had children together, I would not be able to take them anywhere or do normal things with them.”
Dodi Al Fayed, 1997
Diana’s last lover, Dodi Al Fayed was tragically a fleeting romance, with the pair only dating for a few months before being involved in the fatal car crash on August 31, 1997.
The eldest son of of former Harrods owner and billionaire Mohamed Al Fayed, Dodi was romantically attached to a slew of famous women including Winona Ryder and Nancy Sinatra. The pair met back in 1986 at a polo match in Windsor, but didn’t strike up a relationship until 1997.
The infamous photo of the two kissing on a yacht in the south of France signalled to the world that Diana had a new romance in her life, and given that she was officially divorced from Charles at this point, it felt like a truly new beginning.
Tragically, that night in 1997 took both their lives after a fatal car crash took place in the Pont de l’Alma tunnel.