Who Did Princess Diana Date Besides Prince Charles?

Diana fell in love with her bodyguard, Barry Mannakee, who was assigned to her in 1985. Per NBC, in 1992, she opened up about their connection in a conversation with her speech coach and friend, Peter Settelen. Though she didn’t mention Barry by name, the details of their conversation — specifically, her mention of Barry’s unfortunate death due to a motorcycle accident — made it clear who she was referring to.

“I tell you one of the biggest crutches of my life, which I don't find easy to discuss, was when I was 24, 25, I fell deeply in love with somebody who worked in this environment. And he was the greatest friend I've ever had,” Diana told Peter. “I was quite happy to give all this up — well, not all this. At the moment, at the time it was quite something to have all this, just to go off and live with him. Can you believe it?”

Diana clarified that they didn’t have a “sexual” relationship, but she “was always wandering around trying to see him” and “wore [her] heart on [her] sleeve.” Diana explained she was “only happy when he was around.”

James Hewitt and Diana met in 1986. According to Ken Wharfe, her bodyguard from 1987 to 1993, the two instantly hit it off. "She said that their first conversation was completely natural, and it was this that first attracted her to him," Wharfe wrote, per People. “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.”

Their reported affair continued for five years until James was deployed to the Middle East. Even then, Diana sent him love letters. Hewitt published two books about the affair, Princess In Love in October 1994 and Love And War in August 1997 (after Diana’s death).

James Gilby, a car dealer, was a close childhood friend of Diana. In August 1992, The Sun released a transcript of a taped phone call between Diana and James, seemingly confirming their affair. Per Time, during the conversation, James repeatedly called Diana “Squidgy,” “Squidge,” and “darling” — hinting at a romantic connection.

Reportedly, during the call, Diana also expressed concerns about getting pregnant, while James reassured her.

Diana was reportedly seeing art dealer Oliver Hoare from 1992 to 1994. “She needed him at every conceivable moment,” Wharfe wrote about their relationship, per The Sun. “She confided to me that he was the first man who had ever aroused her physically. That admission did much to explain the humiliating events that followed.”

Per reports, when Oliver decided not to leave his wife (Diane de Waldner), Diana started calling him regularly, around 20 times a week. When asked about the rumors during her Panorama interview in 1995, Diana admitted to calling him, but said it was “over a period of six to nine months... a few times, but certainly not in an obsessive manner, no.”

Diana and Will Carling, England rugby captain, struck up a friendship in the mid ‘90s. At the time, his wife Julia Carling claimed the two had an affair. “I am sad that Will put himself in that position, and that the princess did as well. This has happened to her before, and you hope she won’t do these things again, but obviously she does,” Julia told The Daily Mail, per People.

Both Diana and Will, however, denied Julia’s claims. Per People, Will categorized their relationship as “perfectly harmless,” and Diana said she had “done nothing wrong.”

In 2021, Will seemed to change his tune. According to The Daily Mail, he told Eden Confidential, “It 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.”

in 1985, Bryan Adams released a song about Diana — called “Diana” — before ever meeting the princess. In 2003, Bryan’s girlfriend Cecilie Thomsen claimed that the rock star and Diana had an affair in 1996. “I knew Diana had an affair with Bryan," she told The Daily Mail at the time. "Ours was a stormy relationship and Bryan's affair with Diana didn't make it easier.”

Hasnat Kahn is a Pakistani surgeon and cardiologist, who reprtedly had a secretive two-year relationship with Diana (between 1995 and 1997). "She had wanted to marry him," royal biographer Judy Wade told People. "She had this vision that together they could bridge east and west, crossing creeds and continents. They could save lives and make it a better world.”

Apparently, Hasnat rejected her. “They had a bust-up in July, and the romance was rocky," Wade explained. "He didn't want to be a walker to a famous woman. When that broke up, she felt her life was amiss. She was depressed.”

“My main concern about us getting married was that my life would be hell because of who she was,” Hasnat told police after Diana’s death, per Vogue UK. “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.”

Diana and Dodi Fayed dated for a few months before their fatal car crash in Paris on Aug. 31, 1997. They reportedly met at a polo match in 1986, but didn’t reconnect until 11 years later, when Diana, Prince William, and Prince Harry vacationed with Dodi’s family in St. Tropez.

After their trip together, Diana reportedly wrote Dodi a thank you note. “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," the letter read, per the Associated Press. Per Wade, Dodi was “Diana’s distraction” following her devastating breakup with Hasnat.