All the men Princess Diana was ever romantically linked to
On 31 August, the world marked 26 years since the death of Princess Diana. The former wife of Prince Charles (now King Charles III) and mother of Prince William and Prince Harry, Diana remains a much-missed family member and a symbol of kindness and compassion to millions of well-wishers around the world.
Vivacious, intelligent and exceedingly beautiful, Princess Diana was never short of admirers. She was iridescent – always fabulously turned out and with a sparkling sense of humour to accompany. As depicted in The Crown, so much of Diana’s youthful appeal and suitability for her role as Princess of Wales (and entry into the Royal Family) was the absence of scandal and rubbished relationships in her wake. It’s widely thought that the then Prince of Wales was her first official boyfriend – and it’s not hugely surprising given Diana was 19 at the time that their engagement was announced.
On 15 August 1990, Princess Diana and Prince Charles (now King Charles III) were photographed cruising off Mallorca with royals from across Europe. But who joined the windswept Windsors?
The then Prince Charles married Lady Diana Spencer in spectacular fashion in 1981 – their royal wedding was watched around the world. The couple welcomed their two sons soon after but later separated. It wasn’t long into their relationship that Charles resumed his romance with Camilla Parker Bowles (now Queen Camilla), giving Diana license to have her own rumoured relationships. Ultimately the marriage wasn’t to last: following a period of separation, Diana and Charles officially divorced in 1996.
Diana (known as Diana, Princess of Wales, following her divorce) only married once but there was a continual ‘hum’ of speculation as to who she might be ‘seeing’ at any one time. Here are those men – some confirmed as a flame, others as a boyfriend and some may well have never happened at all…
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Bettmann / Getty Images1/10Prince Charles – 1981
King Charles III, then Prince of Wales and the heir to the throne, first met Lady Diana Spencer at Althorp House, her family estate. At the time, he was dating her older sister, Sarah, but would later recall in an interview ‘what fun she was’ during their initial exchange. Their wedding, broadcast to the world, on 29 July 1981 was a hugely lavish occasion – but their marriage, as is well known, wouldn’t stand the test of time. Diana and Charles were officially divorced for just over a year before Diana’s tragic accident; although they had been separated for four years, since 1992. -
Getty Images2/10Barry Albert Mannakee – 1985
Mannakee worked as a police officer with the Royal Protection Squad before being assigned to Princess Diana as a bodyguard in 1985. Palace rumours circulated of an affair between the two of them that ultimately led to his dismissal from the role a year later. In 1987 he was killed in a motorcycle accident that led to conspiracy theories that his death had been planned. These were fuelled by Diana in a video later obtained by NBC, where she confessed, ‘I was only happy when he was around,’ and she described his death as, ‘the biggest blow of my life’. She also said: ‘I think he was bumped off, but there we are.’ He was never mentioned by name in the secret tapes – when she spoke of a man she was in love with – but it was assumed she was referring to him. In the tapes she said she was ‘deeply in love’ with the unidentified security guard and was ‘quite happy to give all this up and to just go off and live with him’. The death of Mannakee was reinvestigated during the inquiry into the death of Diana, as part of Operation Paget, overseen by Sir John Stevens. -
Ron Dadswell / Shutterstock3/10James Hewitt – 1986-1992
The dashing former Household Cavalry officer and tank commander began his five-year affair with Diana in 1986 after they met at a cocktail party, with Diana later confessing to the romance in the 1995 BBC Panorama interview – much contested this past year, 25 years on. The affair happened at the same time that Prince Charles was widely reported to have been seeing his former girlfriend, Camilla Parker Bowles. The metaphorical rug was pulled from under the relationship when Hewitt was deployed to serve in the Gulf War, before splitting permanently, when their affair was exposed. Diana’s former protection officer and confidant, Ken Wharfe, wrote about the affair in his book Diana: Closely Guarded Secret with the cooperation of Hewitt – which was said to leave the Princess heartbroken. The princess later revealed: ‘I was in love with him. But I was very let down’. -
Shutterstock4/10James Gilbey – 1989
The name James Gilbey has become synonymous with the pre-1990 ‘Squidgygate’ incident. Gilbey, the heir to a gin fortune, had been a friend of Diana’s since childhood. She always denied the affair and the former Lotus car executive has never spoken about it – but he claimed a place in royal history as the person on the other end of the line during the ‘Squidgygate’ phone call in 1989 (that was recorded). In it, he called the princess alternately ‘Squidge’ or ‘Squidgy’ 53 times and spoke of wrapping his arms around her and holding her close. The Sun revealed the tapes’ existence in 1992 in which the princess reportedly also complained her husband, Prince Charles, ‘makes my life real, real torture’.
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Shutterstock5/10Oliver Hoare – 1992 to 1994
Diana embarked on an affair with old Etonian art dealer Oliver Hoare, who was 16 years her senior, in the early nineties. Hoare, 46 at the time, was actually a friend of Diana’s husband, Prince Charles, and he and his wife, Diane de Waldner de Freundstein (from a wealthy French oil family) had stayed at Windsor on multiple occasions. In Diana’s former bodyguard’s book Diana: Closely Guarded Secret, Ken Wharfe wrote: ‘The princess was instantly attracted to him. Diana later confessed to me that she had felt a little shy when, at Windsor, she shook his hand for the first time, and had blushed as she flirted with him. That conversation ended abruptly when Charles and the Queen Mother joined them.’ One night, Hoare 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. On another occasion, he was said to have been seen entering Kensington Palace via the boot of Diana’s car. The affair came to an end owing to Hoare’s refusal to leave his wife and Diana is thought to have become a little over infatuated when she rang his Chelsea home 300 times in one night. Hoare died of cancer on 23 August 2018. -
Shutterstock6/10Will Carling – 1995
Former England rugby star Will Carling met Diana – while she was still married to Charles and he married to TV presenter Julia Carling – during an early-morning workout at London’s Chelsea Harbour Club in 1995. Although the relationship has been denied by Carling, Diana reportedly asked for private training sessions which led to a fleeting tryst. In the press, the frisson was blamed for the breakdown of his marriage. Today, he is married to Lisa, the ex-wife of David Cooke, a former rugby union star, and the couple have two children. Post rugby, he founded Will Carling Management Ltd. a corporate hospitality company. -
Getty Images7/10Hasnat Khan – 1995 to 1997
Khan, described by Diana as ‘Mr Wonderful’, was a British-Pakistani heart and lung surgeon thought by friends to have been the ‘love of Diana’s life’. Their two-year-long relationship ended just months before Diana’s death in August 1997 owing to the fact that Khan feared he could never have a normal family life if they married. The couple had reportedly even considered moving to his native Pakistan together before the relationship ended. Khan attended Diana’s funeral ceremony at Westminster Abbey in September 1997. More recently, he’s worked as a consultant in cardiothoracic surgery at Basildon University Hospital, Essex. -
Shutterstock8/10Dodi Al Fayed – 1997
The eldest son of former Harrods owner and billionaire Mohamed Al Fayed, Dodi was a playboy linked to a string of famous women, including Winona Ryder and Nancy Sinatra. Dodi first met Princess Diana at a 1986 polo match in Windsor while she was still married to Prince Charles. In the summer of 1997, Dodi invited Diana (now divorced from Charles), William and Harry to spend time on his yacht in the south of France – Diana later returned to the yacht without her sons and a photo of the pair kissing made headlines around the world. The couple enjoyed a fleeting, jetset romance spending time in the South of France and Sardinia before flying to Paris. It was on 31 August, 1997, after a dinner at Mohamed al Fayed’s Ritz hotel in Paris, that the pair were hounded by the French paparazzi on motorbikes as they drove through the Pont de l’Alma tunnel, when they crashed into a pillar, dying at the scene.
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Getty Images9/10John Kennedy Junior – a rumour
Rumours of an alleged romance came from Diana’s friend and former ‘energy healer’ Simone Simmons in her 2005 book Diana: the Last Word. The rumours have largely been rubbished – including by Diana’s former butler Paul Burrell – but it is true that they met in a secret meeting. Diana and Kennedy met in a Manhattan hotel room in 1995 to discuss Diana posing for the cover of Kennedy’s political magazine, George (Cindy Crawford starred on the inaugural issue dressed as a glamorous George Washington). Diana ultimately declined the cover in a note saying: ‘Thank you so much, but not right now’. -
Getty Images10/10Bryan Adams – a rumour
Rumours have swirled for years regarding a possible tryst between Diana and Bryan Adams, whisperings fanned by Adams’s former girlfriend, actress Cecile Thomsen, who claims the pair had an affair. The pop star wrote the single ‘Diana’ in 1985 about the woman who ‘drove him wild’ although they wouldn’t meet for some time. In 2018, Bryan Adams, addressed the question on Watch What Happens Live saying that he and the late Princess were just ‘great friends’. When asked if she would sneak him into Kensington Palace he told the interviewer: ‘She didn’t sneak me in, I would just roll up’. Adams was in attendance at Diana’s 1997 funeral.
