Royals
Royal Relationships: A Deep Dive Into Princess Diana’s Romances & Rumored Affairs
Princess Diana‘s legacy casts her as both the saint and the sinner.
History remembers Diana as both the revolutionary who changed the face of the British crown forever, and as a hopeless romantic, longing to find the person who would put her first. As half of one of the most famous couples in modern times, Diana’s marriage to then-Prince Charles in 1981 was a fairy tale and a fiction from the beginning. His longtime love for Camilla Parker Bowles haunted their marriage like a ghost, straining what Diana had originally hoped would be the happy ending she had always dreamed of finding.
But just a few years into their union, Diana began having affairs—some she later confirmed and others she denied—that became lightning rods of speculation and scandal for the royal family. In the years since her tragic death in 1997, biographers, close friends, and those who knew her have spilled the beans on these relationships, painting the portrait of a woman in search of the love and devotion her marriage never gave her. Her two sons, Prince William and Prince Harry, have since reluctantly assumed the role of figures of royal fascination for the media and have become endless sources of drama and gossip.
But no one had it quite like Diana, who endured more attention than one person could bear, and never the kind she hungered for. When the cameras weren’t flashing, though, who did Diana give herself to? In addition to Charles, here are the notable men Diana was linked to during and after her marriage.
Prince Charles
The wedding of Princess Diana and Prince Charles was a moment that millions of romance fans can probably point to as their origin story. Of course, there was so much going on behind the scenes, much of which has been aired out for the world to hear and judge in the years since. What we do know is that Charles was 29 and dating his future bride’s older sister when the two first met in 1977, at which time Diana was only 16. He proposed to her on February 6, 1981, at Windsor Castle, and they were married just a few months later in July.
Five years into the marriage, though, the couple could barely hide their issues. Some even called them “The Glums” because their disdain for each other was always on display. She began entering into affairs (detailed below) and he resumed his own affair with Camilla Parker Bowles. By the 1990s, the pair couldn’t escape constant tabloid coverage of their marital strife, battling tell-all books and even recorded phone calls that detailed the strain. On November 20, 1995, Diana participated in a now-infamous interview with Martin Bashir, during which she spoke about her affairs, Charles and Camilla, and her own personal struggles. It was a step too far for Queen Elizabeth II, who wrote to the couple advising them to divorce. The couple had agreed on terms by the summer of 1996, and the divorce was finalized on August 28, ending what many spectators believed would be the love story of their lifetime.
Barry Mannakee
Sometimes the person you are looking for is right in front of you, or rather, in the case of Diana’s bodyguard Barry Mannakee, right beside you. While she publicly denied their relationship ever happened, it is alleged that the two entered into some sort of an affair in 1985 while she was still married to Charles. Their relationship flew in the face of security protocol (don’t all the great loves?) and it all came to a head, according to Tina Brown’s 2008 book The Diana Chronicles, at the wedding of Sarah Ferguson and Prince Andrew in 1986, when Diana’s attention was too obviously fixated on the puppy love she had with Barry. After that, his superiors removed him from her detail, and their relationship waned. He died in a motorcycle crash just a few months later, leaving Diana “devastated,” as she privately told her friend and vocal coach Peter Settelen.
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James Hewitt
That same year, Diana became acquainted with army captain James Hewitt, from whom she took private riding lessons. The two quickly tumbled into a physical relationship that reportedly had them dreaming about a life together—no matter how implausible it was. “I have lain awake at night loving you desperately and thanking God for bringing you into my life,” Diana wrote in a letter to James in August 1989. “I just long for the days when finally we will be together for always, as that is how it should be.”
The affair was passionate and all consuming for Diana, but it wasn’t meant to be. The pair began to fizzle out when he was stationed in Germany in 1989, and their relationship came to an end after he spoke to an author about their time together in 1994. But their relationship was one of the affairs she spoke candidly about in her 1995 Panorama interview with Martin Bashir. “Yes, I adored him. Yes, I was in love with him. But I was very let down,” she said about James.
James Gilbey
The heir to the Gilbey’s Gin fortune, James Gilbey knew Diana before her marriage to Charles. But it wasn’t until she was looking for love or something like it outside that marriage that they reconnected and took things further. Not much is known about the specifics of their time together—and Diana herself denied it in her 1995 Panorama interview. However, there was no denying they had reached some form of intimacy and familiarity when The Sun published recorded phone conversations between the pair on New Year’s Eve 1989. The tapes, eventually known as “Squidgy-gate” because he referred to her several times as “Squidgy,” were a huge scandal for Diana and Charles, and only fueled the flames of rumors about Diana’s extramarital activities.
Oliver Hoare
Some have charged Diana with taking her affairs to the extreme, and many allege that was the case with art dealer Oliver Hoare. Diana and Charles were friends with Oliver and his wife, Diane de Waldner, herself an heiress. But Diana reportedly became infatuated with Oliver, who was more than a decade and a half her senior. Reports from confidantes stated they were sneaking away together during ski trips (where, according to Andrew Morton, she allegedly jumped out of her hotel room window to meet up with him), and she is even said to have smuggled her lover into her Kensington Palace apartment in the trunk of her car.
The relationship was never easy. It always had baggage because of the history they shared with their partners. Things took a turn around 1993, though, when mysterious phone calls were placed to Oliver’s house. A Scotland Yard investigation traced the calls—which were silent whenhis wife answered— to Diana’s mobile phone, Kensington Palace, and nearby payphones. She admitted to Bashir that she made some of the more innocuous calls, but allegedly only copped to the repeated rings in private. The scandal made waves when it broke in 1994 and pushed Oliver to reconcile with his wife, and away from Diana.
Will Carling
In the waning days of Diana and Charles’ marriage, just about any man who entered her orbit was linked romantically to Diana in one way or another by the tabloids. While it has never been confirmed, one of the most popular potential paramours was former rugby player Will Carling in the early and mid-1990s. Will has since denied these claims (on multiple occasions), telling The Telegraph as recently as March 2024 that the rumors and intense speculation were hard to handle. He even wonders if the attention paid to his other relationships were partially to blame for the media firestorm that linked him to Diana, who he says was his friend. “Hey, a lot of that is my own fault, you can’t complain. You have to learn. Relationships that I got wrong… so, that’s what they got fascinated by. You look back on it and you think it was all blown out of all proportion, but it made a good story.”
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Hasnat Khan
Diana gave even the most romantic Grey’s Anatomy storyline a run for its money in 1995 when she fell hard for Hasnat Khan, a British-Pakistani heart surgeon she met while visiting a friend in the hospital. Like many of her former paramours, she threw herself headlong into the relationship, visiting the hospital for days on end, taking an interest in Khan’s work, and becoming a familiar face for the patients who unexpectedly got some bedside attention from a royal. The two would date for two years, before and after her divorce with Charles was finalized in 1996, some of which is seen in Netflix’s The Crown. She would come to call him “Mr. Wonderful,” dreaming as she has done before of a normal-ish life with more children and a husband who adored her.
But after two years, Khan told The Daily Mail in 2012 that things simply had no direction, and the celebrity that lingered over Diana’s every move unsettled him about what kind of life they could have in the spotlight. Years later, he admitted that he tries not to keep himself up at night pondering what might have been had they stayed together. “You never know. She could be living very happily and married and having more kids, with me or with someone else. It could have led in that direction [for us]. I try not to think about these things. I can’t change anything now,” he said.
Dodi Fayed
The final days of Diana’s life were defined by a media firestorm around her new romance with Dodi Fayed, who showered her with the kind of attention and thoughtfulness that she wanted. After meeting him during a stay on his father Mohamed Al-Fayed’s yacht in St. Tropez in July 1997, the two were seen kissing on board in the weeks that followed. It was, of course, the scene of the famous photo of her sitting alone on the end of a diving board in that simmering blue bathing suit (something that was also prominently featured in The Crown). His father was rumored to have pressed Dodi to pursue Diana, and he did as he was told. He made her feel loved, even if some called their time together a fling that wouldn’t outlast the summer.
The world will never know if that was true. Just a few weeks after they first met, Diana and Dodi died in a car crash in a Paris tunnel on August 31. Like each one of Diana’s relationships, the end was not how she dreamed, and that’s what made her story outlive even the People’s Princess.
