Princess Diana’s love life was far from a fairy tale. The beloved “Queen of Hearts” spent much of her life searching for love—yet happiness seemed to always elude her. Her one marriage to Prince Charles ended in heartbreak, and none of the relationships that followed ever turned into “the one.”
That doomed union brought mutual affairs. The media offered mixed reactions to Diana’s romances—some claimed she acted out of revenge or boredom, while others believed she was simply starved for genuine love. Today, we look back at the men who once held a place in Lady Di’s heart.
Barry Mannakee
Together: 1985–1986
Barry was Diana’s personal bodyguard. Though they tried to maintain boundaries, the time spent together drew them closer. When Diana’s marriage began falling apart in 1985, she found emotional refuge in Barry. He was 14 years older and married, so their relationship was doomed from the start—but it gave her a sense of passion and escape.
“I felt like a little girl around him… I wanted to run away and live with him,” Diana once confessed in a home video, later leaked after her death.
When Prince Charles found out in 1986, Barry was reassigned. A year later, he died in a car accident—rumored to have been no accident at all.
James Hewitt
Together: 1986–1988 (possibly until 1991)
Perhaps Diana’s most infamous affair. She publicly acknowledged it in a 1995 interview. The polo player said Diana was affectionate but also emotionally needy and demanding. Their bond was strong, but his military deployment to Germany strained it. They resumed briefly afterward, but by 1991, it ended—partly due to public scrutiny. Years later, Hewitt released a tell-all book, which Diana saw as betrayal. Public backlash forced him to move to Spain.
David Waterhouse
Together: Approx. 1988–1992
A very distant relative of Diana, David accompanied her to official events and even vacations. Though they were close, Diana cut off the relationship, feeling it wouldn’t help her media war against the royal family. He never spoke publicly about her, earning quiet respect.
James Gilbey
Together: Approx. 1989–1992
They allegedly had a romantic history before Diana’s marriage. Their emotional closeness resumed later, evidenced by a leaked 1989 phone call in which Diana shared her sorrows and Gilbey comforted her with affectionate nicknames. It was clear he cared deeply.
Oliver Hoare
Together: 1992–1994
Introduced by Prince Charles, Hoare impressed Diana with his intellect and charm. They became close after her separation from Charles. However, Hoare—married with children—chose his family over her. Diana was devastated and reportedly made over 300 anonymous calls to his home out of jealousy.
Will Carling
Together: 1993–1995
The rugby star met Diana while coaching young princes William and Harry. Their relationship escalated, leading to a tabloid scandal and Carling’s divorce. He has never admitted to the affair.
Hasnat Khan
Together: 1996–1997
Diana called the British-Pakistani heart surgeon the love of her life. She even considered converting to Islam for him. Their romance was intense and secretive—Diana reportedly met him in nothing but a fur coat during private visits. But Khan, overwhelmed by her constant attention and the media spotlight, ultimately walked away.
Dodi Al-Fayed
Together: 1997
Their romance was brief but high-profile. The son of a wealthy Egyptian businessman, Dodi fell hard for Diana. He even planned to propose. Diana, while not as deeply in love, gave him a chance—especially since her sons liked him. Tragically, their relationship ended in the fatal Paris car crash on August 31, 1997.
Each of these men played a role in Diana’s complicated emotional world. Some offered love, others disappointment. But all were chapters in the heartbreaking love story of a woman adored by millions, yet still yearning for someone who truly loved her back.
