A Complete Timeline Of Princess Diana's Dating History

Much attention has been paid to Diana Spencer's love interests during her life and since her death. Though she was married to then-Prince Charles from 1981 until their official divorce in 1995, Diana had a number of romantic interests throughout her adult life. As did Charles, who infamously maintained his affair with Camilla Parker Bowles throughout his marriage to Diana.

When Charles and Diana first announced their romance to the world, she was still a teenager and embodied the sense of innocence and naivety that the royal family deemed acceptable for the then-direct heir to the throne. Someone like Camilla — who had a bit of a reputation for doing things her way — was not appropriate for the future king. Diana was much younger, had hardly a dating history to account for at that time, and was absolutely stunning — the trifecta in the eyes of the firm. As we all know, however, the fairytale between Diana and Charles was incredibly short-lived. Their relationship deteriorated throughout their marriage and was riddled with extramarital affairs. By the time they separated in 1992 and divorced in 1995, the rose-colored glasses had been lifted off the eyes of just about everyone.

Diana tragically passed away in 1997 alongside her boyfriend, Dodi Al Fayed, when their vehicle crashed in Paris, but her romantic life extended far past her last relationship. Here's a complete timeline of her dating history.

When then-Prince Charles was getting into his late 20s and early 30s, he was not only seen as the world's most eligible bachelor, but he was feeling the pressure to get married. His unsuccessful attempts at dating were Britain's worst-kept secret, and his dating history was full of flings and short-lived romances that never took off. When he first met Diana Spencer, Charles was actually dating her older sister, Sarah Spencer, and he met his future wife when she was just a young teen.

Visiting Sarah at the Spencer home at Althorp in November 1977, Charles and Diana met for the first time. Though Sarah was dating the prince at the time, she made it well-known to him that she had absolutely no intention of marrying him, reportedly saying, "[I wouldn't marry him] if he were the dustman or the king of England."

Diana, meanwhile, was just 16 years old — 12 years younger than Charles — and thought the world of him when they first met. In fact, Charles seemingly won her over when he reportedly told her he was "the one man on the planet who is not allowed to divorce [her]." From there, the connection blossomed, but not in the way you might think.

When we think of royal romances, we think of the fairytale. We imagine the prince who would do absolutely anything for his princess, who would sweep her off her feet and connect with her in a way that no one else had before. And while they certainly were the world's favorite prince and princess, Prince Charles and Diana Spencer's early relationship was not at all what you might think. After interacting with one another one-on-one about 12 times, Charles asked Diana to marry him. To say that it was a shock to the 19-year-old is a serious understatement.

By the time the press got wind of Charles and Diana's romance, she was already at the center of intense media scrutiny. The paparazzi followed her wherever she went, and things only escalated when she moved from her London flat to Clarence House. "I know it's just a job they have to do, but sometimes I do wish they wouldn't," a young Diana said of the photographers who would follow her every move. Still, the engagement between her and Charles moved forward, and they two announced their intent to marry in a now infamous press conference. When asked if they were in love, Diana emphatically said yes. Charles, meanwhile, uttered, "Whatever 'in love' means." Some would say that the cracks between them were already forming.

Diana Spencer and Prince Charles got married in 1981, and though the timeline is a bit murky, Charles and Camilla Parker Bowles maintained their friendship — if not their romance — throughout the 1980s. By 1985, Diana was not getting the romantic attention from her husband that any married woman would expect, and she started exploring other dating options. One such man who allegedly caught her eye was Barry Mannakee, the married Scotland Yard officer who was assigned to Diana as her bodyguard. When he and Diana crossed paths for the first time, he reportedly noticed just how strained her marriage to Charles was. There was room for him to get to know Diana on a deeper level.

According to Tina Brown, one of Diana's biographers, a trip to Scotland solidified Diana and Barry's relationship. While sitting on a riverbank, a fish hook from a nearby pole snagged Diana's eyelid. As both her bodyguard and her love interest at the time, Mannakee jumped to her aid and called back up to the house for assistance. When it was clear she needed a doctor, Mannakee didn't hesitate to step in. "It was Mannakee who drove the car, Mannakee, not her husband, who consoled her," Brown noted.

Diana Spencer's relationship with Barry Mannakee was tragically cut short in 1987. While traveling on the A11 highway in Essex around 10 p.m. on May 15, Mannekee was on the back of a motorcycle being driven by friend and officer Steven Peat. Nicola Chopp, a teenager, was driving to meet a friend around the same time and was about to turn right onto the main road. When she noticed the motorcycle being driven by Peat heading toward her, she threw her foot on the brake to avoid running into it. Peat swerved — traveling at about 35 mph — and came to a sudden halt, but Mannakee was thrown from the back seat and crashed into Chopp's windshield. He died as a result of the accident.

In the following years, Diana famously made recordings of herself talking, reflecting on her life and interactions with others. In these recordings, Diana herself believed that Mannakee had been "bumped off" — i.e., killed intentionally to save the royal family from embarrassment. A number of conspiracy theories have surrounded Mannakee's death in the years since, but the truth of its intentions will likely never be known.

Barry Mannakee was just one romantic interest Diana Spencer had in the 1980s. Throughout the decade, she was wooed by retired British Army captain James Hewitt, and their love affair was certainly a well-kept secret around her residence at Kensington Palace. As author Anna Pasternak wrote for the Daily Mail, Hewitt went to extreme lengths to see Diana regularly, even resorting to being smuggled in on occasion.

"Hewitt was regularly bundled into car boots [trunks] and driven to Kensington Palace when their affair ensued," Pasternak wrote. "He told me he was terrified the first night he stayed in Kensington Palace, relieved at least that Charles and Diana had separate bedrooms."

Of the two, Diana's royal bodyguard Ken Wharfe wrote in the book "Diana: Closely Guarded Secret" that their initial interaction stole Diana's heart quickly, as it was easy and carefree. "She said that their first conversation was completely natural, and it was this that first attracted her to him," Wharfe detailed. "They got along famously from the start ... Hewitt told her he was a riding instructor; when she in turn spoke of her long-held fear of riding, he offered to help her overcome it." The two later ended their romance after Hewitt continued to pursue his military career.

Though Diana Spencer was reportedly heartbroken that James Hewitt chose his military career over their relationship, a rather red haired elephant in the room has kept their romance in the public eye all these years later. Of course, we're referring to Prince Harry — Diana's second born son — who looks somewhat similar to Hewitt, notably their shared fiery red hair. Rumors have circulated about Harry's true paternity for years, and for the time being, Hewitt was the only one to address such whispers.

"Admittedly the red hair is similar to mine and people say we look alike," Hewitt said in 2002. "Looking at the pictures I would say he is a much more handsome chap than I ever was. ... There really is no possibility whatsoever that I am Harry's father. I can understand the interest, but Harry was already walking by the time my relationship with Diana began."

Hewitt's estimations stood as the only official comment on the rumors for years, until Harry himself discussed his paternity in his 2023 memoir, "Spare." It marked the first time a royal family member commented on the whispers. "Tabloid readers loved the idea that Prince Charles's youngest son was not Prince Charles's son. They never got tired of that 'joke,' for some reason," Harry wrote, noting himself that Diana and Hewitt's relationship didn't start until after he was born.

By the time the 1990s rolled around, Prince Charles and Diana Spencer's marriage was pretty much over. Their official separation in 1992 seemingly marked the beginning of the end, and the two went about their individual lives despite still being married to one another. One such aspect of Diana's life that carried on was her dating habits, and by 1992, she had already crossed paths with James Gilbey, a close friend. Though their relationship seemed relatively innocent, Diana and Gilbey became front and center in one of the most scandalous reports about a royal — at the time — and it hit the front page.

So what exactly happened? Gilbey had a rather enduring nickname for the princess — Squidgy — and he called her by the sweet moniker during a phone call in the late 1980s. Unbeknown to them at the time, their phone conversation was recorded and given to The Sun in 1992. On August 23, The Sun – a notorious tabloid in the United Kingdom — published the phone call transcript on the front page, highlighting Gilbey's nickname for Diana and dubbing the conversation Squidgygate. The report further alienated Diana from the royal family and highlighted just how dire things had become between her and Charles — not to mention its entirely humiliating publication.

Perhaps one of the most disrespectful aspects of Diana Spencer's dating life came after her death. Former lovers, namely James Hewitt, tried to capitalize off her life and death with books and personal correspondence leaks, but Oliver Hoare was no such man. The art dealer and the princess crossed paths in the 1990s, and the two were reportedly obsessed with one another. Ken Wharfe, Diana's former bodyguard, said, "She needed him at every conceivable moment."

However, Diana and Hoare's relationship didn't seem to extend past the physical element. Wharfe further detailed that the princess told him that while their connection was electric, it was just that. "She confided to me that he was the first man who had ever aroused her physically," Wharfe revealed. Yet, despite how he could've benefitted from sharing their stories, Hoare kept his relationship with Diana close to his chest and never once opened up about their time together. He passed away in 2018 at the age of 73 after having battled cancer, taking all the secrets Diana shared with him to the grave.

One lover who hasn't remained tight-lipped about his relationship with Diana Spencer is Will Carling, the rugby captain with whom she crossed paths in the 1990s. Both were married at the time of their affair, but the rugby captain and the princess extended their relationship past a friendship. In an interview in 2021, Carling admitted that he "stupidly [did] things" he shouldn't have, confessing that his affair with Diana "was a bit of a mess." "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," Carling said on the matter, adding that the immense media attention he garnered as a result of his relationship with Diana was too much to handle.

"You ended up in situations that you shouldn't have been in," he admitted, detailing the lengths he went to to keep their affair out of the public eye. "When I look back ... I rented, not in my name, a flat in Covent Garden with underground parking. It didn't have a phone in it. My parents didn't even know where I lived. I lived there for a year and I never opened the curtains or blinds in case anyone looked in."

Viewers of "The Crown" will have a bit of context for the next love interest that came into Diana Spencer's life. While visiting friend Oonagh Toffolo at Royal Brompton, whose husband underwent heart surgery, Diana crossed paths with British Pakistani surgeon Hasnat Khan. The two were instantly taken with one another and dated from 1995 until 1997. Diana went as far as to call Khan the "love of her life," and Khan himself commented on their relationship after it ended.

"I first met Diana when I had occasion to speak to Mrs. Toffolo, whose husband was required to stay in hospital for some time," Khan detailed. "Diana would visit him on a regular basis. From what she had seen during her visits, Diana became very interested in the workings of the hospital. I found Diana very down to earth and she made everyone feel at ease. I did notice that she was also very flirtatious with everyone. Over a period of time, we became good friends."

Though they were taken with one another, Diana and Khan broke up due to the intense media scrutiny they faced while dating. "My main concern about us getting married was that my life would be hell because of who she was," Khan said. "I knew I would not be able to live a normal life."

Perhaps one of the most tragic stories to come out of Great Britain is the ongoings of the Al Fayed family. Businessman Mohamed Al Fayed extended his time, money, and generosity to the royal family on a number of occasions. While the two parties occasionally rubbed shoulders with one another, things were certainly veiled with classicism. Nevertheless, Diana Spencer met Mohamed's son, Dodi Al Fayed, in 1986 at a polo match when he was competing against her husband, Prince Charles. Though they crossed paths, the two would not rekindle their affection for one another for another 11 years.

By 1997, Diana was facing an extreme amount of press scrutiny and invasive paparazzi. Unlike the years before, she no longer had the protection of the royal family, as her divorce from Charles had been finalized. In an attempt to help her overcome such a difficult time, Dodi and Mohamed extended a vacation offer to Diana and her sons, and they went on holiday for six days during the summer season. "This comes with all the love in the world and as always a million heartfelt thanks for bringing such joy into this chick's life," Diana wrote to Dodi after the holiday was such a fun success. Their relationship blossomed from there, and the two became romantically involved with one another.

Diana Spencer has been immortalized in the public eye, yet the truth of August 31, 1997, will never truly be known. In Paris, France, at the time, Diana and Dodi Al Fayed left the Ritz — owned by Mohamed Al Fayed at the time — in the early morning hours in an attempt to evade the paparazzi that had been camped out at the hotel. Hopping into a Mercedes driven by Henri Paul, the two — plus Diana's bodyguard — attempted to cross town. Tracked down by craning photographers, Paul stepped on the gas to lose them when their vehicle crashed in the Pont de L'alma tunnel, traveling at about 121 mph. Dodi and Paul were killed in the crash, and Diana sustained massive internal injuries.

Though she was transported to the hospital, the princess succumbed to her injuries and died at the young age of 36. Her sons, Prince William and Prince Harry, were just 15 and 12 at the time. Prince Charles went on to marry Camilla Parker Bowles in 2005, and Mohamed has since spent his years maintaining his belief that Diana and his son Dodi were killed in an attempt to stop them from getting married. As Mohamed attests, he believes that British agencies engineered the crash to stop Diana from pursuing a relationship with someone who was Muslim. The truth regarding her tragic death will never be fully known.