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Turns out Princess Diana and Camilla Parker Bowles were not the only women vying for Prince Charles’ love and affection. While Camilla eventually snagged the Prince of Wales out from under Diana, Charles’ close relationship with Lady Dale Tryon once threatened the couple’s happily ever after. So after all the drama, did Charles feel guilty for how he treated Diana throughout their marriage?

Prince Charles Princess Diana
Prince Charles and Princess Diana | Tim Graham Photo Library via Getty Images

Camilla Parker Bowles Was Not Charles’ First Rumored Affair

Charles and Camilla first met in the 1970s. But after their romance fizzled out, they both went on to marry different people. Charles tied the knot with Diana while Camilla exchanged vows with Andrew Parker Bowles.

As royal watchers are well aware, Camilla and Charles had an affair during his marriage to Princess Diana, a scandal that eventually led to their respective divorces. His actions would reportedly come back to haunt him with Princess Diana’s untimely and shocking death in 1997.

After they rekindled things in public, Charles and Camilla got married in a low-key ceremony in 2005. But before they exchanged vows, Camilla Parker Bowles reportedly felt threatened by another interested party. According to Express, Charles was very close with Dale, with whom he reportedly developed a tight bond.

“He did in fact have a dalliance with an Australian woman, Lady Dale Tryon,” Angela Mollard, an expert on the royals, shared. “They just adored each other. They saw each other all the time.”

It should be noted, however, that it is unclear if Charles and Dale were ever romantically involved. Not only were they good friends, but she was the wife of one of Charles’ best pals.

What happened to Dale?

Dale was married to Anthony Tryon, who was a part of Charles’ closest circle of friends. In fact, Prince Charles and Dale met after Anthony introduced them.

They quickly struck up a friendship and discovered that they shared many similar interests. This includes a love for fly fishing, which they both enjoyed doing together.

While we do not know if Prince Charles and Dale ever got romantic, he once admitted that she was the only person “who ever understood me.”

Dale tragically passed away in the fall of 1997. In the years prior to her death, Dale had suffered numerous injuries that resulted in her being paralyzed and unable to walk.

Camilla Parker Bowles has never discussed Charles’ relationship with Dale in public, though it is clear that they shared a close bond. We may never know the truth about what happened, but Dale was hardly the only woman who had a lasting effect on Charles.

Princess Diana’s death still pains Prince Charles

Diana and Charles got hitched in a fairytale ceremony in 1981, but it was not long before their marriage showed signs of cracks. After having two children together, Prince William and Prince Harry, the couple split in 1992.

They did not finalize their divorce, however, until 1996. Princess Diana would tragically pass away a year later from injuries sustained in a car accident in Paris.

Royal author Penny Junor wrote about how Charles dealt with Diana’s death in her book, The Firm. Junor claims that, as the mother of his two boys, Charles loved Diana deeper than anyone expected.

He took her tragic passing very hard and dealt with a lot of grief in the weeks and months following her death.

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“Deep down Charles loved Diana – she was the mother of his sons after all – and he was overwhelmed by the tragedy of both her life and death,” Junor explained.

Junor added that Prince Charles and Princess Diana enjoyed some happy moments together. But at the end of the day, Charles was sad that he could not make things work out with Diana.

Prince Charles and Camilla Parker Bowles are currently ramping up their royal duties amid rumors Queen Elizabeth wants to retire when she turns 95.

Did Prince Charles feel guilty about Princess Diana?

In the years following Diana’s death, many rumors circulated that Charles felt a tremendous amount of guilt over his ex-wife’s passing.

But according to Junor, the Prince of Wales did not feel guilty about what happened. Charles reportedly did everything in his power to make their marriage work, and they both came to realize that they were simply not meant for each other.

That said, Prince Charles still feels pain over the fact that he could not make things work with Princess Diana, especially for the sake of their children. At the time of their divorce, William and Harry were still in their formative years.

“Charles didn’t feel guilty in any way, either about Diana’s death or about his affair with Camilla Parker Bowles,” Junor wrote. “He knew that he had done everything in his power to make his marriage work, but he had failed, and the failure was what hurt – and it still hurts him to this day.”

Prince Charles has never commented on the rumors surrounding Princess Diana’s passing or his relationship with Dale. Although he clearly wishes things would have turned out differently, everything worked out in the end with Camilla Parker Bowles.