In July 1981, the night before his glamorous wedding to Princess Diana, Prince Charles reportedly wept as he was still torn about his feelings for his former girlfriend (and then-mistress) Camilla Parker-Bowles.

According to Prince Charles: The Passions and Paradoxes of an Improbable Life, a new biography of the Prince of Wales by royal writer Sally Bedell Smith, Charles felt pressured into his marriage to Diana — and he was still torn abut his love for the then-married Camilla.

The story of Charles and Camilla is well-documented — the two dated after being introduced in 1971, beginning a love affair that would make headlines for decades. According to Bedell Smith, Charles liked that Camilla was down-to-earth, loved the countryside and wasn’t interested in fashion. They also shared the same sense of humor and he was drawn to the fact that she “always listened.”

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It seemed natural that Charles would be attracted to upper-class Camilla — Lady Annabel Goldsmith tells Bedell Smith that Camilla was “an intensely warm maternal laughing creature, with enormous sex appeal.”

Despite having an apparently happy relationship, the two split up when Charles was stationed overseas with the Royal Navy in 1973.

Patricia Mountbatten, the daughter of the late Lord Mountbatten, tells Bedell Smith there were “obvious problems” with Camilla and she “had a history” — i.e., a sexual past with her on-again, off-again boyfriend (and eventual husband) Andrew Parker-Bowles.

“You didn’t want a past that hung about,” says Mountbatten.

What’s more, Bedell Smith says that when Camilla and Charles split he was only 24 and wasn’t interested in settling down. Shortly after Camilla and Charles broke up, she reconciled with Parker-Bowles and they got married in 1973.

But Charles and Camilla couldn’t stay away from one another for too long. Parker-Bowles was one of Charles’ friends and they all traveled in the same circles. Eventually, the two started up an on-again, off-again affair, with Camilla’s husband turning a blind eye.

By 1980, when Charles began dating Diana, the pressure was mounting for him to settle down. Despite their 13-year age difference, Diana seemed like a good match — she was aristocratic, fun-loving, beautiful and didn’t have a known “history.” However, Charles didn’t appear to be in a rush to get married. That changed, according to Bedell Smith, when the press began speculating that Charles and Diana had spent two nights together. (Diana denied the claim at the time.)

Still, Prince Philip sent a letter to Charles saying that Diana’s reputation was on the line and that he had to make a decision about their relationship. Charles read it as an order to get engaged, but he “wasn’t in love, he wasn’t ready. Psychologically he assumed his father bullied him, so he read it as a bullying letter,” writes Bedell Smith.

However, Bedell Smith said the letter was more a statement that “Charles should either propose to her or release her. In either event, he should make a decision shortly.” The couple got engaged in February 1981 and were married in July of that year.

But the strains around the relationship were already starting to show before the two even walked down the aisle. (Diana famously cried during a polo match ahead of the wedding and had previously said that she had wanted to call everything off.) Bedell Smith writes that the two were just too different — Diana was over a decade younger than Charles and they didn’t have the same hobbies.

Diana also didn’t take to some of Charles’ more traditional habits. Historian Paul Johnson recalled a story Diana had told him about how Charles’ valet would lay his shirt on the bed before he got dressed and if he wanted a new shirt he would ring the valet to bring him a new one. When she asked why he didn’t get his new shirt himself he replied, “He’s paid to do it.”

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