King Charles III’s Entire Dating History, From 1968 to Now

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When you think about King Charles III: chances are, you think about his rather, erm, messy love life. More than likely, you think about his infamous love triangle with his first wife Princess Diana, and later second wife Queen Camilla. This drama brought on a lot of controversy that follows Charles to this day.

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However, Charles had quite a few shocking, and rather serious, relationships with many “it” girls before his first marriage. In fact, he reportedly proposed to a bunch of them multiple times to no avail until Diana, in a desperate attempt to marry before 30, per Marie Claire.

But after some time, he wed Princess Diana in 1981, and after an unhappy union and a long-awaited divorce, he remarried again in 2005 to his on-again-off-again girlfriend and former mistress Queen Camilla.

While we already know most of the story about Diana and Camilla, what about the other ladies? What about the almost-fiancees, brief flings, and the other alleged mistress? And what about the other member of the Spencer family that almost became the Princess of Wales? It’s a wild ride, to say the least, so buckle up.

Check out everyone Charles was linked to over the years, from brief flings to alleged mistresses.

See everyone, and all the details, below.

  • Lucia Santa Cruz

    Image Credit: Photo by PA Images via Getty Images.

    Often referred to as “the first real love of his life,” the daughter of the former Chilean ambassador to London Lucia Santa Cruz was Charles’ first public relationship.  Shortly after enrolling in Cambridge University in 1967, Charles met Lucia at a mutual friend’s dinner party, per the Independent.

    The two dated from 1968 to 1970, and according to author Jonathan Dimbleby, Lucia was actually the one to introduce Charles to his future wife Camilla Shand.

  • Lady Jane Wellesley

    Image Credit: Photo by Tim Graham Photo Library via Getty Images.

    So Charles and Lady Jane Wellesley dated briefly from 1973 to 1974, and they eventually parted ways. The blame was reportedly placed on intense media scrutiny, and when asked about it, Wellesley said, per Independent, “Do you honestly believe I want to be queen?”

  • Davina Sheffield

    Image Credit: Photo by Tim Graham Photo Library via Getty Images.

    Described once as “the soulmate he was searching for,” per Marie Claire, Charles reportedly fell head over heels for the granddaughter of industrialist Lord McGowan, Davina Sheffield. When they first met, she was already seeing someone, but the two eventually started dating in 1976. However, they didn’t last long, and it’s reported she didn’t walk down the aisle because she wasn’t a virgin, per Independent.

  • Sabrina Guinness

    Image Credit: Photo by Tim Graham Photo Library via Getty Images.

    Charles had another brief relationship in 1979 with society “it” girl Sabrina Guinness. Now, things were a bit serious, but it ended up being short-lived since the Queen was reportedly upset about Guinness’ wild past, per Evening Standard.

  • Lady Sarah Spencer

    Image Credit: Photo by Tim Graham Photo Library via Getty Images.

    Before dating her younger sister Princess Diana, Charles was linked to Lady Sarah Spencer in 1977. However, their courtship was short-lived, with Sarah claiming she wasn’t in love with him. She said to Time magazine in 1978, “There is no chance of my marrying him. I’m not in love with him. And I wouldn’t marry anyone I didn’t love whether he were the dustman or the King of England,” per DailyMail.

    Not only that, she’s the one that introduced him to Diana.

  • Lady Amanda Knatchbull

    Image Credit: Photo by Tim Graham Photo Library via Getty Images.

    Back in 1980, Charles fell again for Lady Amanda Knatchbull, also known as the granddaughter of Lord Mountbatten (who was actually the person who introduced the two, per Evening Standard!) Royal expert Howard Hodgson said in the 2007 book Charles: The Man Who Will Be King, “She was equally impressed with his energy, enthusiasm, sense of fun, kindness and modest self-deprecation. She was indeed a very sensible and loving girl, who genuinely did share all the same interests as the heir to the throne.”

    Charles even proposed to her, but she turned him down because she didn’t want to deal with the royal spotlight.

  • Anna Wallace

    Image Credit: Photo by Tim Graham Photo Library via Getty Images.

    Right before meeting Princess Diana in the summer of 1980, Charles dated socialite Anna Wallace the same year. He proposed to her twice, but she denied him both times. Author Jessica Jayne claimed Wallace broke it off after Charles ignored her at Queen Mother’s 80th birthday party, while others claim it was due to his relationship with Camilla. She said, “Charles had taken her to two successive balls and then danced with Camilla for most of both evenings. Anna dumped him with the words: ‘No one treats me like that – not even you,’” per Express.

  • Lady Dale Tryon

    Image Credit: Photo by Tim Graham Photo Library via Getty Images.

    One of the most confusing things in Charles’ dating life was his relationship with alleged mistress fashion designer Lady Dale “Kanga” Tryon (Who he once called “the only woman who ever really understood me!”)

    They originally met back in 1966 at a school dance in Victoria, Melbourne, but didn’t become good friends until 1977 when she married Anthony Tryon. Per New York Post, their alleged relationship happened when Charles was still seeing Camilla, and Dale allegedly named Charles the godfather of her second child.

    Then he married Princess Diana, and then allegedly stopped his relationship with Camilla and Dale for a bit.

  • Lady Diana Spencer

    Image Credit: Photo by Tim Graham Photo Library via Getty Images.

    Lady Diana’s sister introduced the two when Charles was 28 and Diana was 16, and the two didn’t become romantic until 1980. Rumors started to swirl about the two in 1980, when people noticed how many events she was invited to. He proposed to her, and at first, she denied it, but the couple later announced their engagement in Feb 1981.

    They married five months later in a lavish ceremony in St Paul’s Cathedral, later welcoming two children named Prince William, born June 1982, and Prince Harry, born Sept 1984.

    A few years into their marriage was when Charles reportedly started up his affair with Camilla Parker Bowles again (and later, Diana had an affair with  former Army officer James Hewitt!)

    Diana reportedly confronted Camilla saying, “Camilla, I would just like you to know that I know exactly what is going on between you and Charles. I wasn’t born yesterday.” 

    Camilla reportedly replied: “You’ve got everything you ever wanted. You’ve got all the men in the world to fall in love with you and you’ve got two beautiful children. What more do you want?” Diana then replied: “I want my husband.”

    They started to separate, and after her bombshell interview with the BBC, the Queen allowed Diana and Charles’ divorce to be finalized in 1996.

  • Queen Camilla

    Image Credit: Photo by Daniel Leal – WPA Pool/Getty Images.

    After their mutual friend Lucia Santa Cruz introduced the two, Charles and Camilla instantly fell for one another. 

    Back in the early 1970s, they dated officially for around six months before he left to serve in the Royal Navy. Then, when he returned, she was already engaged to someone else: Andrew Parker Bowles. She and Andrew married in 1973, and Charles went on to marry Princess Diana in 1981. However, the two started an infamous affair, and then when Charles and Diana seperated in 1993, Camila and Andrew did the same in 1995.

    Charles and Camilla started dating officially again in 1997 and moved in together in 2003. They got engaged in 2005, and married in a civil ceremony in April 2005. They’ve been together ever since.

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