A Timeline Of All King Charles And Diana's Rumored Affairs

No ill-fated love story has been as highly publicized for as long as King Charles and Princess Diana's. After marrying in 1981 and welcoming Prince William and Prince Harry soon after, Charles and Diana's relationship began to crumble. There were plenty of signs that King Charles and Princess Diana weren't going to last. Charles was determined to get married. There was a stark age gap between the two. It seems that Charles wasn't actually in love with Diana from the jump — when a BBC reporter asked the couple after their engagement if they were in love, Diana responded, "Of course," while Charles answered, "Whatever 'in love' means." Their relationship was doomed. 

But perhaps the most telling sign that Charles and Diana were destined for divorce were the multiple affairs they both allegedly engaged in (Charles reportedly before his marriage, too). No two people have ever wanted out of a marriage more than King Charles and Princess Diana. Here's a timeline of all their affairs. 

It's been alleged that King Charles' affairs began long before he ever married Princess Diana. According to reports, then-Prince Charles exercised his first bout of infidelity while he was dating Camilla Parker Bowles in the early 1970s. Said affair was supposedly with Dale "Kanga" Tryon, an Australian designer whom Charles reconnected with through her husband, Anthony Tryon, 3rd Baron Tryon (Charles and Dale reportedly first met at a school dance in Melbourne). Dale moved to the U.K. in 1972 to launch her fashion career in earnest, and the following year she married Anthony. According to the New York Post, Charles once referred to Dale as "the only woman who ever really understood me."

More details about Dale and Charles' alleged affair were shared in the documentary "Prince Charles' Other Mistress." According to the film, Charles remained connected to Dale while he had a relationship with Camilla outside her first marriage, but he stopped seeing both Dale and Camilla when he married Diana (though as is known, Charles' affairs eventually picked back up). Even more interesting, Dale and Diana became friends. "[Camilla] was the enemy, and on the basis that my enemy's enemy is my friend, [Diana] could see that there was some purpose in having an alliance with Dale," royal expert Christopher Wilson said in the documentary of the apparent rationale behind their relationship. The alleged affair eventually stopped for good, but Dale remained part of Charles' social circle until the late 1990s when her health declined and she subsequently died.

Then-Prince Charles might've stepped outside his marriage first, but he wasn't the only one to do so. Princess Diana had extramarital affairs, too, and one was allegedly with her bodyguard Barry Mannakee, whom she first met in 1985. In a recording, Princess Diana once said, "I tell you one of the biggest crutches of my life, which I don't find easy to discuss, was when I was 24, 25, I fell deeply in love with somebody who worked in this environment. And he was the greatest friend I've ever had," as reported by NBC News, and she's thought to be talking about Mannakee, though Diana never confirmed the man's identity.

Diana went on to note that she tried to see him as much as she could, and that being around him made her happy. The princess said she saw him as somewhat of a father figure, and she wanted to be praised by him. Diana never confirmed whether her relationship with the man became physical, but they did apparently discuss running away together. "I was quite happy to give all this up ... At the moment, at the time it was quite something to have all this, just to go off and live with him. Can you believe it?" she said. "And he kept saying he thought it was a good idea, too." Mannakee tragically died in a motorcycle accident in 1987, and Diana reportedly believed that he was intentionally killed to stop their relationship from continuing. "That was the biggest blow of my life, I must say. That was a real killer," Diana said of his death.

King Charles' relationship with Camilla Parker Bowles has been one of the most infamous on-again, off-again relationships in modern history. The two met in 1970, and Charles and Camilla's lives were never the same. The two began dating soon after, only to break up for good — or so it seemed — before Camilla's marriage to Andrew Parker Bowles in 1973. Charles went on to marry Princess Diana in 1981, and five years later, in 1986, their affair began. The infidelity, unsurprisingly, did not sit well with Diana, and in 1989, she confronted Camilla. "I said, 'I know what's going on between you and Charles, and I just want you to know that.' She said to me: 'You've got everything you ever wanted. All the men in the world fall in love with you, and you've got two beautiful children, what more do you want?' So I said, 'I want my husband,'" Diana said to Andrew Morton, which was later published in the book "Diana: Her True Story," as reported by Time.

Camilla and Charles went on to get divorced from their partners in 1995 and 1996, respectively. By 1999, they took their relationship public, and by 2005, they were married. "Nobody likes to be looked at all the time and, you know, criticized ... But I think in the end, I sort of rise above it and get on with it. You've got to get on with life," Camilla said to Vogue of the affair.

Dancing wasn't the only secret Princess Diana hid from King Charles when their marriage was on the rocks. In 1995, Princess Diana shocked the world by admitting that she had been unfaithful in her marriage to then-Prince Charles. In the famous BBC "Panorama" interview, Diana confirmed the information to Martin Bashir saying, "I was in love with him. But I was very let down," alluding that she knew that Charles had been unfaithful, too, which prompted her to step out herself. "There were three of us in this marriage, so it was a bit crowded," she famously said.

The man that Diana had fallen in love with was James Hewitt, a military man she met at a party in 1986. "Their first conversation felt natural, she said, and it was this that sparked her attraction. As she put it, they got along famously," Ken Wharfe, Princess Diana's bodyguard, claimed in his book "Diana: Closely Guarded Secret," as reported by Town & Country. Hewitt offered to give Diana riding lessons as she confided in him that she was afraid of horses. Once the lessons began, so did the affair. "Hewitt, a natural womaniser, gave her the attention and affection she relished, and then the passion she yearned for," Wharfe said. But the affair wasn't meant to last, and at the end of the decade, Hewitt left England to advance in his career. "Diana felt betrayed: he had chosen his career over her ... When James refused to give up his career, Diana let the affair wane," Wharfe said.

According to the British media, whenever one man exited Princess Diana's life, another found his way in. In 1992, The Sun released recordings of Diana speaking on the phone with James Gilbey, a friend she'd known since well before she married then-Prince Charles. In the conversations, which were recorded on New Year's Eve of 1989, Gilbey repeatedly called the princess "Squidgy," which resulted in the leak being referred to as "Squidgygate." "Diana was like a caged bird trapped in Sandringham," journalist Emily Andrews said of the event's night on an episode of "Secrets of the Royal Palaces," as reported by the Daily Mail. "And when we get to New Year's Eve of 1989, there she is, actually all alone in her room – except she wasn't. She had a telephone."

The journalist continued, "The wife of the heir to the throne being intimate over the telephone in a royal palace with someone who wasn't her husband ... He acts almost like the husband that she wanted Charles to be. He acts as her confidant." Aside from the nature of the phone call, not much else is known about the alleged affair between Diana and Gilbey. Diana denied that the two were romantic, and, although many things were learned about Princess Diana after her death, Gilbey has never publicly addressed the rumors. The same year that the tapes were revealed, however, Diana and Charles officially separated, and a few years later, in 1996, Charles and Diana finally divorced. 

Oliver Hoare also never publicly commented on his alleged affair with Princess Diana. In 1992, not long before officially separating from then-Prince Charles, the late royal allegedly began an affair with Hoare, one of Charles' friends. Charles and Camilla were also having a relationship at this time, and Diana reportedly sought clarity from Hoare as to why her husband was so in love with Camilla. Diana allegedly called Hoare's home almost nonstop, with some sources saying as many as 20 calls per week at one point.

It's also been said that Diana did not take well to the end of their alleged affair. "Diana was very naughty. She would drive to his house and park up outside and then call his house phone from her mobile. She'd do it in the middle of the night, so she could watch the lights in the house go on as he scrambled to the phone. She would be there for hours, watching and calling," a source told the Mirror of her behavior post-breakup. The source alleged that Hoare had no intention of leaving his wife. "Diana would always say, 'I know he will never leave his wife'. But she wasn't used to not getting her way. So she would enjoy taunting him and reminding him she was there."

Royals have the privilege of getting to meet anyone they want, and apparently King Charles wanted to meet Barbra Streisand. The pair first met in 1974 upon his request. As Streisand said in her memoir, "My Name Is Barbra," "The fact is, both Prince Charles and I are shy, but somehow we still managed to connect, because that proved to be the beginning of an unexpected friendship," as reported by The Sun. Twenty years later, while then-Prince Charles was still married to Princess Diana and dating Camilla Parker Bowles, Streisand performed at Wembley Arena in London, and Charles watched the show from the Royal Box. "He wrote, 'It was such a treat to attend your concert last night — you were wonderful and I adored every minute!'" Streisand said, alluding to a bouquet of flowers he sent.

Not long after the performance, Charles invited Streisand to spend the night at Highgrove. The two had a candlelight dinner and Streisand said she later retired to a bedroom. She and Charles spent some time together the next day. Streisand has never admitted to having a physical relationship with Charles, nor has the monarch, but it has been alleged by some that the two were more than just friends at some point in the mid-90s. "The Prince is the most ­gra­cious host and made every­thing easy for me," Streisand said.