Inside Princess Diana’s Loves, Heartbreaks, and True Romances

When 20-year-old Lady Diana Spencer walked down the aisle of St Paul’s Cathedral on July 29, 1981, she truly believed she had found her happily ever after with Charles, who was then Prince of Wales. “I remember being so in love with my husband that I couldn’t take my eyes off him,” Andrew Morton writes, quoting the princess, in Diana: Her True Story in Her Own Words. “I just absolutely thought I was the luckiest girl in the world. He was going to look after me.”

Although she was already aware of her husband’s feelings for his (now wife) Camilla Parker Bowles, Diana tried hard to be everything the serious-minded, country-loving husband wanted her to be. And for a short time, it worked. After Diana’s funeral in 1997, Prince Charles himself sadly confided in a friend, “You know, whatever they say, when we got married we were very much in love.”

But the marriage quickly turned sour. Hopelessly mismatched, Charles and Diana were growing increasingly apart after the birth of Prince Harry in 1984. Young and inexperienced, Diana was devastated by her husband’s lack of interest and his reignited affair with Camilla, which sparked her deep abandonment issues from childhood.

Throughout her short life, Princess Diana was looking for idealized storybook love, often at the expense of her mental health and common sense. Alleged romances and extramarital affairs seem to have been a result of Diana searching for comfort and confirmation that she was worthy of being adored. “Diana needed more love than any Englishman can give.” friend Hugo Swire recalled.

At an age when most women were dating and exploring their sexuality, Diana found an outlet flirting with courtiers and companions. “She used to collect men,” one friend told Sally Bedell Smith, author of Diana in Search of Herself: Portrait of a Troubled Princess, “in the old-fashioned romantic way. She would give you a look with lowered eyes.… You knew deep down it was a game she played, and a very clever one in a way, not cynical, but by doing this, she won everybody over.”

Diana’s first alleged affair began in 1985, when she rather predictably fell head over heels for her bodyguard Barry Mannakee. “For a woman in a golden cage, bodyguards are an obvious candidate for romantic fixation,” Tina Brown writes in The Diana Chronicles. “A bodyguard may be the only real man a princess meets. His strong shoulders clear the path ahead in the crowd. His firm hand on her elbow guides his principal to the refuge of a waiting car.”

Mannakee, a warm, strong “cocky East Ender with kind eyes,” was equally besotted with the beautiful princess. When palace brass became aware of what was happening, Mannakee was warned he was being overly friendly with Diana, but he didn’t care. His head swelled with a case of what bodyguard Ken Wharfe called “red carpet fever.”

As for the princess, she was utterly obsessed. “I was only happy when he was around,” she told her friend Peter Settelen in a taped conversation, seemingly referencing Mannakee. “I was like a little girl in front of him the whole time, desperate for praise. Desperate.”

But the lovers were playing with fire. Brown writes:

On the eve of Sarah Ferguson’s marriage to Prince Andrew on July 23, 1986, the inevitable happened. Mannakee and Diana were allegedly discovered in a compromising position. During the next day’s ceremony, Andrew Morton watched Diana closely from the press gallery at Westminster Abbey. He noted that she seemed uncharacteristically distracted during the wedding of her then best friend.

Caught red-handed, Mannakee was quickly transferred to another position. A few months later, he died in a motorcycle crash. Prince Charles chose to tell Diana of Mannakee’s death in their car on the way to the Cannes Film Festival. “[I] just sat there all day going through this huge high-profile visit to Cannes, thousands of press, just devastated,” Diana later told Settelen. “Because, you know, I wasn’t supposed to mind as much as I did.” Diana publicly denied having had a physical relationship with Mannakee.

Her next romance was with army captain James Hewitt, a dashing, handsome charmer who Diana claimed had his head “inside his trousers,” would come to cause Diana intense embarrassment and pain. “Yes, I adored him. Yes, I was in love with him. But I was very let down,” she told Martin Bashir during her infamous 1995 Panorama interview.

The two met in the fall of 1986, and Diana quickly asked Hewitt, a cavalry officer, to give her private riding lessons. According to Hewitt, the princess, “deeply damaged by rejection,” made the first move, telling him: “I need you. You give me strength. I can’t stand it when I’m away from you. I want to be with you. I’ve come to love you.”

Highly sexually compatible, the two spent happy weekends together at Hewitt’s mother’s cottage, where Diana, in a pattern that would become familiar to those she loved, threw herself into everything, including the country pursuits that Hewitt enjoyed. They daydreamed of a life together, picking out their future home in Country Life and playing with Prince William and Prince Harry, who, according to Brown, grew fond of Hewitt.

“I have lain awake at night loving you desperately and thanking God for bringing you into my life,” Diana wrote to Hewitt in August 1989. “I just long for the days when finally we will be together for always, as that is how it should be.”

But this pipe dream was shattered when Hewitt was posted to Germany in 1989, although the two continued a sporadic physical relationship (Hewitt would let Diana down in 1994, when he shared details about their relationship with Anna Pasternak for the book Princess in Love). In the meantime, Diana began an alleged affair with gin heir James Gilbey, an old friend from her single days.

It was Gilbey on the other end of the phone in the infamous “Squidgygate” conversation illegally taped on New Year’s Eve 1989, while the princess was with the royal family at Sandringham. In the call, he is supportive and almost sycophantic, something Diana clearly craved as her marital woes were increasingly thrust into the public eye.

“She was the sort of person who didn’t like being out of a relationship,” Diana’s former trainer Carolan Brown recalled. “She didn’t like being on her own because she needed constant reassurance that she was loved.” In the 1995 Panorama interview, Diana denied the allegations of an affair with Gilbey.

If Diana’s relationship with Gilbey was lightweight, her next one would reportedly drive her to the brink of madness.

Sixteen years Diana’s senior, Oliver Hoare was a sophisticated, suave, and supremely cultured art dealer who was married to Diane de Waldner, a wealthy French heiress. Initially friends of Prince Charles, the Hoares were reportedly attempting to help mend Charles and Diana’s fractured marriage.

Instead, Hoare became Diana’s latest obsession, and she became a regular visitor to his London art gallery. They began meeting clandestinely at the homes of friends and having breakfast at the Chelsea Harbor Club. The relationship was volatile and filled with drama, with the couple going to great lengths to secretly spend time together.

According to Andrew Morton’s Diana: In Pursuit of Love, while on a skiing holiday in Austria in 1993, Diana jumped out of her hotel room 20 feet above ground one evening—presumably to rendezvous with Hoare, who was staying at a nearby hotel.

The pair went to comical lengths to hide from the press and prying palace eyes, but it’s unclear to what extent their machinations fooled those around them. According to Morton, Princess Margaret delighted in spying as Diana snuck Hoare into her Kensington Palace apartment in the trunk of her car.

Between 1993 and 1994, Hoare began receiving dozens of harassing phone calls to his home. When de Waldner answered, she was met with silence. An investigation by Scotland Yard traced the calls to Diana’s mobile phone, Kensington Palace, and nearby payphones. Diana initially denied making the calls, and later told Bashir that she called “a few times, but certainly not in an obsessive manner.” Brown details that she eventually confirmed the rumors to her confidant Joseph Sanders:

The Princess admitted to her confidant Joseph Sanders that she had been going out at night to make the pay phone calls, wearing various disguises and gloves to cover her fingerprints. Sanders exploded. “You know you’re a very silly girl to behave like this and you shouldn’t think you can get away with it,” he told her. He called the next day to apologize for his impertinence. Diana laughed. “Oh, don’t worry, the Palace are shouting at me the whole time.”

In the fog of love, Diana truly believed Hoare would leave his wife and marry her once she was officially divorced. “Oliver Hoare was naughty,” a friend told Brown. “He led her on.”

She was lifted out of her haze in August 1994, when News of the World broke the story, calling Diana a “royal phone pest.” Hoare, reconciled with his wife, did not defend her, devastating Diana. “It was a very, very painful relationship for her,” her astrologer Debbie Frank said. “We often talked about it. But through the pain she learned something about herself.”

Indeed, lessons from this crazed affair and Diana’s growing inner confidence and sense of self would lead her to the man many believe was the great love of her life.

Hasnat Khan was a 36-year-old British-Pakistani heart surgeon at Royal Brompton Hospital. In September 1995, Diana was visiting her friend Joseph Toffolo who was recovering from heart surgery, when the man Diana called “Mr. Wonderful” entered the room. Morton writes:

Heart surgeon Hasnat Khan was running to fat, smoked a pack of cigarettes a day, and had a passion for Guinness, Carlsberg lager, Kentucky Fried Chicken, and late-night jazz. Yet the moment Princess Diana set eyes on the unprepossessing figure of the Pakistan-born surgeon her heart skipped a beat. ‘He’s drop-dead gorgeous,’ she told her friend Oonagh, after their brief encounter.

According to Morton, over the next 18 days Diana was a constant visitor in Toffolo’s room, much to his amusement. A besotted Diana was soon shadowing Khan in his rounds at the hospital, comforting patients, and even watching him perform heart surgery. The two started dating and Diana began reading Gray’s Anatomy and the Quran (Khan came from a Muslim family), and watching the hospital drama Casualty.

In Khan, Diana saw a man with a pure heart and altruistic spirit. “He was a male version of what she wanted to do—save lives and give to people,” one friend recalled.

For his part, Khan was smitten with Diana’s down-to-earth friendliness. “[He was] the first man who was completely unimpressed by her glamour,” Diana’s friend Cosima Somerset remembered. “He liked her for herself.”

In many ways, they were a remarkably normal couple. Diana would join him in disguise, queuing up for jazz clubs in London. She would spend days doing housework in his apartment, or in her place eating KFC Hasnat brought after his shift. Of course, there were sexier moments—according to Diana’s former butler Paul Burrell, she once greeted him in nothing but a fur coat and her sapphires and diamonds.

“She was emotionally more stable when she was with him,” a friend of Diana’s told Bedell Smith. “He taught her that she could be loved.”

Diana seemed aware of this fact, telling one friend, “I found my peace. He has given me all the things I need.”

Diana envisioned a future with Khan: marriage, more children (hopefully girls), and a life building hospitals for underprivileged children. “She felt that Hasnat and her could change the world,” a friend noted.

And Khan believed in her. “She did good things because she wanted to, not because of her status,” he recalled. “She had an inner desire. It genuinely came from within her.”

But Diana knew that a new marriage (she and Charles were officially divorced on August 28, 1996) would cause a media frenzy and perhaps upset her beloved sons. “If I fall in love with somebody else the sparks will fly and God help us,” she reportedly told Prince Charles.

Yet it was her celebrity to blame for the romance’s undoing. The affable and unassuming Khan not only worried about the difference in their cultures but his ability to handle life in the public eye. “My main concern about us getting married was that my life would be hell because of who she was,” he said. “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.”

They broke off the relationship in the summer of 1997, leaving Diana devastated. But Khan would always wonder what might have been. “In retrospect, there are one hundred could-have-beens,” he said in 2012. “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.”

Soon after the breakup, Diana accepted an invitation from billionaire owner of Harrods Mohamed Al-Fayed to vacation at his St. Tropez compound in July 1997 with her sons.

It was here she met Mohamed’s son Dodi, a boyish, generous, and supremely irresponsible playboy (model Kelly Fisher claimed that she and Dodi were allegedly engaged at the time). Egged on by his father, he began wooing Diana over subsequent vacations, showering her with gifts and affection.

Many of Diana’s intimates believe the relationship was simply a “summer fling.” When the pair were photographed kissing on the Al-Fayeds’ yacht, the Jonikal, in August, friends believed it was a shot across the bow at Khan, Diana’s way of getting his attention.

But for Dodi, it was something deeper. “He was very happy and I thought that he had found someone,” his uncle Hassan Yassin recalled. “For the first time in his life he was blossoming.”

There were perks for Diana as well: glamour, sunshine, unlimited funds to protect her, and a man who had all the time in the world to dote on her and wasn’t afraid to do it in public.

“She was blissfully, ecstatically happy, having really one of the best times in her life, and Dodi was very much part of that,” her stepmother Raine Spencer recalled. “One of the reasons Diana fell in love with him was because he was such a sweet, thoughtful person and he thought all the time about her. This she told me only a few weeks before she died. She said to me, ‘I’m so happy, at last here is somebody who thinks about me.’”

Who knows what would have happened if Diana and Dodi hadn’t died following the car crash in that dark Paris tunnel on August 31, 1997. What we do know is that, over her life, Diana’s relationships had evolved from the desperate longings of a troubled girl to mature, fulfilling relationships with men who admired and adored her. She had also begun to discover that the greatest love story of all is the one you have with yourself.