Princess Diana's Many Love Affairs

Diana had numerous documented affairs while married to Charles. She contributed to the breakdown as much as Charles did when it came to adultery, but even though she liked being the “People’s Princess”, her dark side was the “Queen of Manipulation”. You cannot rationalize that she had a right to these affairs because of Camilla. She was responsible for her actions. Diana had FIVE extramarital affairs over a ten-year period several long term.

Infidelity is often framed as a simple moral failure, but in real life it is a complex human event with multiple causes. People who cheat may be in pain, confused, or acting from unexamined patterns—not because harm doesn’t matter, but because motives are rarely one-dimensional. Understanding this complexity doesn’t excuse betrayal or minimize the impact on partners. It does, however, help us respond with clarity instead of contempt, compassion instead of condemnation, and boundaries grounded in self-respect rather than punishment.

Causes can be personal. Attachment wounds from childhood, trauma, or insecure bonding can fuel a search for affirmation outside a relationship. Low self-esteem, depression, or anxiety may drive someone toward novelty to feel alive or worthy. Some experience identity crises—around aging, career, parenthood, or sexual orientation—and seek an affair as a mirror to a lost or emerging self. Others struggle with impulse control or untreated addiction. Sometimes it’s less dramatic: poor coping skills and avoidance make a secret feel easier than a difficult conversation.

Causes can be relational. Many affairs grow in the space between partners—longstanding conflicts left unresolved, a breakdown in emotional or sexual intimacy, or mismatched desires and expectations. Overwork, caregiving, postpartum shifts, chronic illness, and financial stress can exhaust a couple’s capacity to connect. When communication patterns turn critical or distant, a third party can become a shortcut to feeling seen. None of this means the injured partner “caused” the affair; it means the relationship context matters if healing or parting is to be thoughtful.

Causes can be situational and cultural. Opportunity and secrecy—travel, long-distance living, alcohol, permissive peer cultures—lower barriers. Digital platforms offer anonymity and constant access. Cultural scripts that glamorize conquest, stigmatize vulnerability, or teach people to equate worth with desirability can distort choices. Social isolation and lack of community support can make people lean on the wrong lifelines. Again, these are explanations, not excuses; responsibility still includes honesty, consent, and accountability for impact.

Why avoid judgment? First, judgment rarely helps those harmed. It can inflame shame, entrench defensiveness, and block the deep work of repair or separation. Compassion does not mean permissiveness; it means holding people accountable without reducing them to their worst moment. Second, judgment often ignores the unknowns: power dynamics, mental health, cultural pressures, or histories we can’t see. Third, non-judgment protects our own integrity. We can set firm boundaries, speak truth, and choose our path without becoming punitive or self-righteous.

If you’ve been betrayed, your pain is real. Seek support, prioritize safety, clarify boundaries, and move at your pace. If you’ve betrayed, take responsibility, tell the truth, accept consequences, and do the inner work to understand why—ideally with a therapist. As a couple, slow down, avoid snap decisions, and let actions—not promises—show what’s possible. Whether you stay or part, choose growth over blame. We don’t have to judge to learn. We can honor the harm, uphold our values, and still hold space for people to become better than their mistakes.

Princess Diana, the beloved “People’s Princess,” lived a life often shaped by public scrutiny and personal trials. Her relationships, both within and outside her marriage to Prince Charles, were a subject of global interest, sparking countless discussions about love, duty, and personal happiness. Here’s an overview of some of the men Diana was known to have had affairs with:

Extramarital Affairs

Barry Albert Mannakee, 1985

Mannakee was employed as Diana’s bodyguard in 1985 but was dismissed just one year later after rumours began circling of an affair between the two. In 1987 he was killed in a motorcycle accident which was said to have upset Diana deeply.

In private tapes recorded with Diana’s voice coach, Peter Settelen and released after her death, Diana spoke of Mannakee without naming him, saying: “I was only happy when he was around,” and that she would have been “quite happy to give all this up and to just go off and live with him. And he kept saying he thought it was a good idea too.”

In the same tape, she described his death as, “the biggest blow of my life,” before insinuating that his death had not been caused by a freak accident.

“I think he was bumped off, but there we are,” she said.

Will Carling, 1995

During an early-morning workout at London’s Chelsea Harbour Club in 1995, Diana met former England rugby star Will Carling, who was married to TV presenter Julia Carling at the time. After their meeting, Diana reportedly asked for private training sessions which lead to a fleeting romance.

When it was publicly revealed that Will had visited the Princess at Kensington Palace, as proven by his tell-tale blue Range Rover spotted in the car park, Julia publicly fired a warning shot at Diana, declaring that she had “picked the wrong couple”.

“It would be easy to say she’s ruined my marriage, but it takes two to tango and I blame Will for getting involved in the first place,” she said, just a year before they divorced.

Will adamantly denied the rumours, but in 2021 made comments about “behaving stupidly” which sparked speculation that he was confessing.

“It was a bit of a mess,” he told the Eden Confidential.

“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. Never intentionally or vindictively, I just think that was me, I just was in a bit of a mess.”

James Hewitt, 1987

Perhaps the most well-documented of Diana’s relationships was with James Hewitt, a former cavalry officer. Diana admitted to the affair in a 1995 interview. The two reportedly met at a party in 1986, and the relationship lasted several years. Hewitt was often a confidant to Diana during her tumultuous marriage to Charles, and their close bond drew significant attention and speculation, especially due to Hewitt’s striking red hair, leading to rumors—denied by those involved—about him being the biological father of Prince Harry.

James Gilbey, 1989

Known from the infamous "Squidgygate" tapes, James Gilbey, a car dealer and longtime friend, was overheard having an intimate phone conversation with Diana in 1989. The tapes, filled with affectionate exchanges, suggested a close relationship, but not much is known beyond what was captured in the tapes themselves.

Oliver Hoare

Diana allegedly had a relationship with art dealer Oliver Hoare, a friend of Prince Charles. Reports of this affair emerged after it was revealed that Hoare often visited Kensington Palace and that Diana made numerous phone calls to him. Although their liaison was much speculated, Hoare was married at the time, and the full extent of the relationship remains speculative.

Post Breakup With Charles

Hasnat Khan

Before Dodi Fayed, Diana was romantically linked with Hasnat Khan, a Pakistani heart surgeon. Their relationship was reportedly serious, with Diana reportedly considering converting to Islam to marry him. Known for being media-shy, Khan represented stability for Diana, though their different worlds and media pressures ultimately contributed to their breakup.

Dodi Fayed, 1997

Diana’s relationship with Dodi Fayed, the son of billionaire Mohamed Al-Fayed, was highly publicized in the summer of 1997. Although their romance was brief, lasting just a few months, it captured the world's attention primarily because of their tragic deaths in a car crash in Paris.

Throughout these relationships, Diana's personal struggles were palpable. Her marriage to Prince Charles was fraught with challenges, including his longstanding relationship with Camilla Parker Bowles. Diana’s affairs were, in many ways, a search for affection and understanding -- refuge from her tumultuous and often lonely life within the Royal Family.

Her relationships were often portrayed as acts of defiance against the monarchy, seen by many as a breach of royal protocol and duty. However, they were also deeply human responses to rejection and unhappiness. Her disloyalty, as it was labeled by some, was indicative of her desire for personal healing and love, amid an environment that frequently felt cold and isolating.

Diana’s life was a complex tapestry of public duty and personal agony, with her romantic relationships being a testament to her quest for authenticity and connection in a life dictated by royal expectations and media sensationalism.

So instead of deifying her and heaping pity on her, let’s focus on her humanity and how she truly did make a difference and stop blaming Camilla. And let’s take it a step further and quit vilifying Camilla for her looks.

One thing I have learned from 65 years on this planet is that when true love hits, physical appearance no longer matters.

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