The fairy-tale marriage of Prince Charles and Lady Diana Spencer captivated the world when they wed in a lavish ceremony in 1981. However, behind the scenes, their relationship was far from a storybook romance.
Plagued by incompatibility, extramarital affairs, and the pressures of royal life, the couple’s marriage was troubled from the start.
Despite being married and a mother to two young princes, Diana found herself seeking comfort and companionship from other men throughout her tenure as Princess of Wales.
From dashing military men to wealthy playboys, Diana’s rumored and confirmed relationships with a string of suitors became tabloid fodder and fueled scandal.
Even 25 years after her tragic death, the world remains fascinated by the intimate details of Diana’s love life and the men who captured her heart.
1. Early Years
Diana first met Prince Charles in 1977 when he was dating her older sister, Lady Sarah McCorquodale.
At the time, Diana was just 16 years old and, according to Charles, he recalled thinking “what a very jolly and amusing and attractive 16-year-old she was” after their first meeting.
It wasn’t until 1980 that Charles and Diana began courting, and after a whirlwind romance, the couple announced their engagement in February 1981. Their fairy-tale wedding on July 29, 1981, was watched by a global television audience of 750 million.
Diana, dressed in an ivory silk taffeta and antique lace gown with a 25-foot train, was the picture of a blushing bride.
However, even on her wedding day, there were signs of trouble.
Diana confessed years later that she felt like “a lamb to the slaughter” and had confided in her sisters that she wanted to back out of the wedding.
2. Barry Mannakee (1985-1987)
Barry Mannakee, a police officer with the Royal Protection Squad, was assigned as Diana’s bodyguard in 1985. The two developed a close bond, and rumors swirled of an inappropriate relationship.
According to Diana’s former protection officer Ken Wharfe, the princess confessed that Mannakee was the “greatest love” she ever had.
In a secretly recorded video, Diana revealed, “I was deeply in love with someone who worked in this environment.
Eventually he had to go and then three weeks after he left, he was killed in a motorbike accident.
He was the greatest love I’ve ever had, and that was definitely the most devastating blow in my life.”
Mannakee was abruptly transferred from his role in 1986, and a year later, he died in a tragic motorcycle accident that some believe was not an accident at all.
“I think he was bumped off,” Diana said in the tapes.
“We’ll never know. He was greatest fella I’ve ever had.”
3. James Hewitt (1986-1991)
Major James Hewitt, a handsome, red-haired cavalry officer and polo player, met Diana at a cocktail party in 1986.
According to Anna Pasternak’s book “Princess in Love,” their affair began after Hewitt offered to give Diana riding lessons.
“Only one thing went wrong,” Hewitt later revealed in his tell-all book. “We fell in love.”
Their secret five-year affair took place at the same time Prince Charles was widely reported to be having his own extramarital relationship with Camilla Parker Bowles.
Hewitt was smuggled into Kensington Palace to spend the night with Diana, and the two would enjoy time together on the royal estates of Highgrove and Sandringham.
“Hewitt was regularly bundled into car boots and driven to Kensington Palace when their affair ensued,” Pasternak wrote in The Daily Mail.
“He told me he was terrified the first night he stayed in Kensington Palace, relieved at least that Charles and Diana had separate bedrooms.”
The affair came to an end in 1991 when Hewitt was deployed to serve in the Gulf War.
In her infamous 1995 BBC Panorama interview, Diana admitted to the relationship, saying, “Yes, I adored him.
Yes, I was in love with him. But I was very let down.”
4. James Gilbey (1989)
Old Etonian James Gilbey, a Lotus car executive and gin heir, was a childhood friend of Diana’s.
In August 1992, The Sun published the transcript of a scandalous taped conversation allegedly between Gilbey and Diana.
In the intimate phone call, Gilbey referred to the princess as “Squidge” or “Squidgy” 53 times and told her repeatedly, “I love you.”
At one point, Gilbey said he yearned to “fill your tank full of kisses.” The incident became known as “Squidgygate.”
Although Gilbey has never publicly spoken about the nature of his relationship with Diana, the leaked phone call suggested the two were more than just friends.
Gilbey later married interior designer Lavinia Hadsley-Chaplin in 1994.
5. Oliver Hoare (1992-1994)
Married art dealer Oliver Hoare was 16 years Diana’s senior and a friend of Prince Charles when he began an affair with the princess in 1992.
A source close to Diana’s staff claimed that the princess had fallen “completely in love” with Hoare and that he was the first man who had “aroused her physically.”
Hoare was caught by a palace guard hiding behind a potted tree while smoking a cigar after sneaking in to see Diana.
On another occasion, a fire alarm went off in the middle of the night inside Kensington Palace, and Hoare was found hiding in a cupboard.
“She begged him to leave his wife and marry her,” Pasternak wrote of Diana in The Daily Mail.
“He refused, saying he loved his wife and children deeply.”
Their affair reportedly ended in 1994 after the princess became “obsessed” and started calling Hoare’s home up to 20 times a week.
Hoare passed away from cancer in August 2018 at age 73. 6. Will Carling (1995)
England rugby captain Will Carling met Diana at the Chelsea Harbour Club, an exclusive gym in London, in early 1995. The two shared a passion for exercise and struck up an instant rapport.
Rumors of an affair between the high-profile pair ran rampant in the tabloids, although Carling has always denied any inappropriate relationship.
However, in a 1996 TV interview after Carling had split from his wife Julia, the sportsman hinted that he had indeed been intimate with Diana.
“I’m not angry or bitter about what happened. It was very difficult for everybody, but I’m not going to sit here and say she was a bad person,” he said.
“She was a wonderful person.”
7. Hasnat Khan (1995-1997)
Perhaps the most significant relationship Diana had after her separation from Charles was with Pakistani heart surgeon Hasnat Khan, whom she dated from 1995 to 1997. Diana affectionately called him “Mr.
Wonderful” and friends have said she described Khan as the love of her life.
“She wanted to marry him, even if that meant living in Pakistan,” Jemima Khan, a close friend of Diana’s, told Vanity Fair in 2013. “And that’s one of the reasons why we became friends.”
However, the cultural differences between the couple ultimately led to their split just months before Diana’s death.
Khan was reluctant to take on the publicity that came with being associated with the most famous woman in the world.
“My main concern about us getting married was that my life would be hell because of who she was,” he later told police in an official interview.
“I knew I would not be able to live a normal life.”
Diana was said to be brokenhearted by the end of their relationship.
“She wanted a husband to be there for her, to support her and to have a family with,” said her friend Rosa Monckton.
“She wanted somebody who was strong, but she also wanted somebody who could cope with the things she couldn’t cope with.”
8. Dodi Fayed (1997)
Diana’s last romantic relationship was with Dodi Fayed, the jet-setting son of Egyptian billionaire Mohamed Fayed.
While vacationing in the South of France during the summer of 1997, paparazzi photos captured Diana and Fayed in intimate embraces aboard a luxury yacht.
Their brief and intense romance was tabloid fodder, with speculation that Fayed had gifted Diana with lavish jewels, including a reported $200,000 Bulgari diamond necklace.
Some friends believed that Diana’s relationship with Fayed was a ploy to make Khan jealous and lure him back.
Tragically, the couple’s romance ended in heartbreak when they were both killed in a car accident in Paris on August 31, 1997, as their driver tried to evade the paparazzi.
Fayed and Diana had only been dating for a few weeks at the time of the fatal crash.
9. Rumored flames
Although never confirmed, Diana was linked to several other high-profile men during her lifetime.
In the mid-90s, Diana struck up a friendship with John F. Kennedy Jr., who had just launched George magazine.
The two met for a secret meeting in a New York City hotel room in 1995 to discuss the possibility of Diana appearing on the cover, dressed as George Washington.
Ultimately, Diana declined the offer.
Canadian singer Bryan Adams was also rumored to have had a fling with Diana.
His 1985 song “Diana” about a woman who “drives him wild” fueled speculation that the two were an item.
In 2018, Adams’ former girlfriend claimed that the rocker and the princess were having an affair, but Adams has vehemently denied any romantic relationship, insisting they were just friends.
From her ill-fated marriage to Prince Charles to rumored flings with celebrities, Diana’s love life was a source of constant intrigue and speculation.
Despite her affairs, friends say that Charles was the true love of Diana’s life and that her ultimate goal was to live happily ever after as his wife and the future Queen.
“The boys were central to both our lives,” Diana said of her marriage in a 1995 TV interview.
“There was so much love in that marriage. There was so much love for those children.
I just pray that love will override any other feelings of anger, resentment, or bitterness that they may have.”
More than two decades after her death, the world remains captivated by the People’s Princess and the intimate details of her personal life.
From her charity work to her fashion sense to her romantic entanglements, Diana left an indelible mark on history.
Her legacy as a devoted mother, humanitarian and style icon continues to inspire new generations of fans who feel a deep connection to the princess and her enduring spirit.
