Their wedding might have looked like the real-life fairy-tale ending to a great love story, but as we all soon learned, Prince Charles and Princess Diana’s relationship was anything but smooth sailing. Not only did the Princess of Wales later make a surprise confession about the worst day of her life, but most of her marriage seemed overshadowed by tears, drama and—more than anything—the infamous public love triangle.

So you might be surprised to learn that the beloved princess, who died in an August 1997 car accident in Paris, and the now King Charles shared a tender moment crying together. And we bet you can’t guess when and why it happened!

A royal expert dropped the revelation in a British TV documentary, and we have the scoop. Read on to find out what exactly happened—and to get more insights into the marriage the whole world talked about.

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When did Charles and Diana share this heartfelt moment?

Believe it or not, King Charles and the late Princess Diana wept together in August 1996, the day they finalized their divorce and officially ended their marriage of 15 years.

Ingrid Seward, the editor of Royalty Magazine, spilled about the private moment in the Channel 5 documentary The Royal Family at War. “Diana did tell me something quite interesting,” the royal expert claimed. “She said that on the day of the divorce, she and Charles sat down together on the sofa, and they both cried.”

So what does that mean? Were the two mourning their failed marriage—or was there some regret on one or both sides?

Not according to royal expert Richard Fitzwilliams. He thinks that while the heartfelt moment might come as a bit of a surprise to the public, it has to be placed into context. “It seems once Charles and Diana accepted that their marriage was over, they both did have a natural feeling of sadness,” he says. “But there was also a lot of mutual exhaustion after fighting their relationship battle in public for so many years that might have just caused this emotional moment.”

What was their relationship like when they divorced?

Princess Diana Prince Harry Prince William And Prince CharlesPrincess Diana Archive/Getty Images

It seems Charles and Diana got along slightly better once they had decided to call it quits. “It was this crazy separation, but by the time the divorce was finalized, they were on much better terms,” Seward said in the TV documentary.

Fitzwilliams also feels like “things had calmed down a little between the two” once they officially went their separate ways. “They had their own lives and their children to look after,” he says. “Their marriage was a disaster from early on, but despite the bitterness between them, they were both very good parents to Prince William and Prince Harry throughout.”

Diana and Charles went on to co-parent and tried to spare their sons from any additional heartbreak. Of course, their “competition in public” didn’t disappear entirely after the divorce, Fitzwilliams says. “Diana upstaging the 50th birthday party Charles threw for Camilla by showing off her swimwear on her holiday in St. Tropez—she certainly knew how to pull a front page,” he says. Fitzwilliams is referring to the famous pictures of the late princess sunbathing on a speedboat in a leopard-print swimsuit while on vacation with boyfriend Dodi Fayed. They landed in the tabloids the very day Camilla Parker Bowles—the current queen, the “other woman” in Charles and Diana’s marriage, and Charles’s official partner by then—celebrated her birthday.

Away from the public eye, however, it seems the estranged couple still managed to put their differences aside once in a while. “At the end of Diana’s life, she and Charles were on the best terms they’d been for a very long time,” writes Tina Brown in her bestselling book The Diana Chronicles. “Charles got into the habit of dropping in on her at Kensington Palace, and they would have tea and a sort of rueful exchange. They even had some laughs together.”

Was Charles having an affair with Camilla at the time of the divorce?

Charles admitted to having an affair with Camilla in a candid TV interview in 1994—two years before he and Diana officially divorced but two years after they had publicly announced their separation. During the much-talked-about interview, Charles was asked if he had been “faithful” to Diana and replied, “Yes, absolutely.” He paused, then said, “Until it became irretrievably broken down, us both having tried.”

Charles’s confessions made headlines around the world, with many royal fans shocked about the revelation.

It’s pretty safe to say, though, that neither of the two women involved in the love triangle were particularly surprised. As Fitzwilliams notes, Camilla had been the elephant in the room from day one in Charles and Diana’s marriage. Camilla was invited to the royal wedding, as her then-husband, Andrew Bowles, was the commanding officer of the Household Cavalry Mounted Regiment at the time.

“Diana was looking for her while she walked down the aisle,” Fitzwilliams says. “And while Charles said he had only started his new relationship when his marriage had already turned sour, Diana believed the two had had an affair even before her wedding, and it had just never ended.”

Who filed for divorce?

Despite having been separated since 1992, it was only in late 1995 that Charles asked for an official divorce. Queen Elizabeth II actually encouraged the final move, following Charles’s cheating confessions on British television and Diana’s TV interview the following year, during which she famously said, “There were three of us in this marriage, so it was a bit crowded.”

Nonetheless, Diana initially didn’t want a divorce. “Her own parents had been deeply unhappy after their divorce, so she didn’t want to repeat history,” Fitzwilliams says. “But after she gave that interview, it was inevitably going to happen.”

Diana eventually gave in, and the divorce came through in August 1996. The princess later called that day the saddest of her life.

How did Charles and Diana relate to each other in their marriage?

Diana And Charles In SevilleTim Graham/Getty Images

Fitzwilliams believes Charles and Diana were “two completely mismatched individuals” who should never have wed in the first place. “They were total opposites, and they hardly knew each other when they got married,” he says. “They had only met 13 times, after all, before they walked down the aisle. Unlike Camilla, Diana was very young and inexperienced, and she didn’t share Charles’s sense of humor or group of friends.”

That being said, it seemed after they tied the knot, they turned into each other’s support system for a while, especially since they both made their sons a priority and wanted to bring them up in a loving home.

“They certainly had their happy moments, especially when it came to their children, and they might have even tried to make things work for a while,” Fitzwilliams says. In the end, though, they couldn’t get past the big issues. “While Diana saw red when it came to Camilla, Charles resented that Diana took the spotlight away from him. People were more interested in seeing her, even though he was the future king.”

About the expert

  • Richard Fitzwilliams is one of Britain’s most prominent royal experts and commentators. He has followed the lives of the royal family for decades and regularly shares his expertise with media outlets around the world.

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Sources:

  • Richard Fitzwilliams, royal expert; phone interview, Oct. 15, 2024
  • Channel 5: The Royal Family at War (March 2019)
  • The Diana Chronicles by Tina Brown
  • Harper’s Bazaar: “A timeline of Princess Diana and Prince Charles’s whirlwind romance”
  • Newsweek: “Did Princess Diana show off to paparazzi on Camilla’s birthday?”
  • Time: “How Charles and Diana’s relationship changed after divorce”
  • BBC: “The life of Diana, Princess of Wales (1961-1997)”
  • Town & Country: “When did Prince Charles and Diana divorce?”
  • New York Times: “Prince Charles, in TV documentary, admits to infidelity”
  • Tatler: “Prince Charles said he was ‘living dangerously’ when publicly admitting adultery”
  • Today: “Charles and Camilla: A timeline of the king and queen’s relationship”