A Complete Look At King Charles' Dating History

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Since Queen Elizabeth II's death, all eyes have been on King Charles III, formerly Prince Charles. As she departed this world and her throne on September 8, the queen left a decades-long legacy behind and very large shoes to fill. The heir to the throne, Charles, was immediately made king upon her passing and Camilla Parker Bowles was made the queen consort. In an announcement that came as a huge shock to many, Elizabeth made it clear that Camilla — who has had a rocky relationship with the royals and the British public for years — would be named queen consort when Charles ascended the throne, despite initial plans to be named princess consort only.

"When, in the fullness of time, my son Charles becomes king, I know you will give him and his wife Camilla the same support that you have given me," the late monarch revealed during her Platinum Jubilee. "It is my sincere wish that, when that time comes, Camilla will be known as Queen Consort as she continues her own loyal service."

The late monarch's wishes have since been fulfilled and Camilla is presiding as queen alongside Charles. And it's no wonder that people have been reflecting on Diana Spencer and the legacy she left behind after her tragic death in 1997. Further still, others are wondering who Charles romantically crossed paths with during his bachelorhood — who could have taken Camilla's place had the king not married his longtime mistress?

Davina Sheffield may have been King Charles' 'soulmate'

While many would assume that Camilla, Queen Consort, is King Charles III's soulmate, another woman almost snagged the title way back in the day. Davina Sheffield gave the king a run for his money and was said to be "the soulmate he was searching for," royal expert Penny Junor wrote in her book, "The Firm: The Troubled Life of the House of Windsor."  When the two first crossed paths, Davina — the granddaughter of Lord McGowan and sister-in-law to former prime minister David Cameron — was 24 years old and a dazzling beauty to behold. She was also said to be a perfect match for the then-prince in more ways than one, as she had a great pedigree and shared similar interests.

There was a snag, however. When Charles and Davina first met, she was in a relationship with another man — a powerboat racer named James Beard (how salacious does that sound!?). But according to Junor, Charles was so hell-bent on pursuing Davina that she eventually turned the tides of her own romantic connection. "Charles was so persistent that she eventually succumbed and the boyfriend soon fell by the wayside," Junor wrote.

Davina and Charles were not seen as a suitable match

Things seemed to be moving swimmingly for Davina Sheffield and King Charles III during their relationship — until they came to a grinding halt. Penny Junor noted in her book, "The Firm: The Troubled Life of the House of Windsor," that while the two were "very much in love" and a proposal was on the horizon, Davina's ex started getting hunted by the media as to the status of the relationship and what she was like as a person.

During the media flurry, it was revealed that Davina and James Beard had "lived in sin" and that was the last nail in the coffin, as Marie Claire noted. Royal tradition was, and is, very much a part of the monarchy, and at the time, a bride for any future monarch needed to be "intact" — referring to exactly what you think (via Marie Claire). "It killed the relationship stone dead," Junor wrote, detailing that Charles was extremely upset over the falling out.

It certainly wouldn't be the first time that royal tradition would get in the way of Charles' love life, however. As noted by Biography, Queen Camilla was once viewed in the same perspective, being dubbed "experienced" by the royal family. Because she had a well-known relationship with Andrew Parker Bowles, had dated around, and was not considered "pure," she was not seen as a suitable fit for the king.

One of Charles' exes has sordid familial history with the royals

Before the topic of his singlehood became a major talking point in the press, King Charles III was linked to Caroline Longman, whose family had been well connected to the royals for quite some time. As noted by the Daily Mail, Caroline's mother, Lady Elizabeth Lambert, was a close friend of Queen Elizabeth II's and served as a bridesmaid at her wedding to Prince Philip. After Caroline was born, her parents named the queen her godmother, and the monarch and Lambert enjoyed a long friendship (via Tatler).

When Charles and Caroline began dating in the 1970s, they were said to enjoy attending polo matches together and were often seen driving around in the then-prince's Aston Martin. Clearly, the relationship didn't work out, but from what we can tell the two families continued to enjoy a long friendship well into Lambert's 90s.

That's not the only way Caroline and her family are linked to the royals, though. As it happens, Caroline's sister is Rose Hanbury, a high-profile member of British high society who was alleged to be engaging in an affair with William, the Prince of Wales. As noted by Cosmopolitan, sources close to both the royal couple and the Hanburys were adamant that the cheating rumors weren't true. In fact, Princess Catherine and Hanbury were planning a charity event together at the time. Still, that didn't stop the rumors from spreading, and affair allegations once again flooded the headlines in August 2022.

Charles went on to date his cousin

When King Charles III was single once again, another woman caught his attention — Amanda Knatchbull, who happened to be his cousin. In his book "Battle of Brothers," Robert Lacey explained that the former Prince of Wales was "very fond" of his cousin. In fact, their bond was so strong that Charles' great-uncle Lord Mountbatten, who was said to be a close confidant of the then-prince, was supportive of a proposal. "Over the years the two cousins did grow close, developing a mutual respect and friendship that has lasted to the present day," Lacey wrote.

Now, let's address the elephant in the room. Yes, it's weird that Charles and his cousin were dating, but this wasn't out of the ordinary for royals. In fact, as noted by Reader's Digest, it was quite common for royals to marry one another during the European dynastic era, as marriage was more of a political union than a romantic one. Additionally, the late Queen Elizabeth II and her husband, Prince Philip, were distant cousins — they both shared a lineage with Queen Victoria.

His proposal to Amanda was rejected

When we discuss the royal family as a whole, the word "duty" is thrown in there a lot. Queen Elizabeth II is perhaps the greatest example of fulfilling her royal duty — not only was she the longest-serving monarch in British history, but she often made personal choices with a sense of royal commitment at the forefront. Simply put, the crown was always first. This is an attitude among royal family members that is common knowledge, and it was this expectation that Amanda Knatchbull reportedly did not want to live up to. In his book "Battle of Brothers," Robert Lacey discovered that King Charles III proposed to Amanda in 1979, and Amanda — who was described as an independent thinker — gave him an unequivocal no.

"'The surrender of self to a system,' she explained, was so absolute when joining the royal family, it involved a loss of independence 'far greater than matrimony usually invites,'" Lacey wrote, explaining that Amanda's denial of Charles' hand in marriage forced the then-heir to the throne to reconsider his priorities (via Yahoo).

Lacey's words were bolstered by Jonathan Dimbleby, who, per Express, noted that turning him down only further bolstered Charles' "own belief that to marry into the House of Windsor was a sacrifice that no-one should be expected to make."

Charles and beer heiress Sabrina Guinness dated for less than a year

Back in the day, King Charles III was named the world's most eligible bachelor, and fans waited anxiously to see with whom he'd tie the knot (via Calgary Herald). Sabrina Guinness — of that Guinness company — was one such contender, as noted by the Daily Mail. She and Charles bonded over a variety of hobbies. In addition to sharing a love of polo, he and Sabrina connected over fly fishing and theater. Things got so intense between the two of them that Charles' aunt, Princess Margaret, was said to have called their relationship "serious" — and royals don't throw around that word casually.

As the Daily Mail reported, however, there were some snafus along the way. For instance, while visiting Balmoral, she went to sit down on a specific chair. The late monarch reportedly jabbed at her, telling her to get up as it was "Queen Mary's chair." If we know anything about the royals, it's that first impressions and etiquette matter.

By the time things were getting even more established, Sabrina told the press that while she enjoyed being with Charles, "he's not ready for marriage yet." That comment may have been the lethal blow to the relationship because, after less than a year, Charles called it quits.

Guinness finally shook the title of Charles' ex

So what exactly happened between King Charles III and Sabrina Guinness? Well, Charles was said to have "dropped her," and it came as little to no surprise to anyone around them, per the Daily Mail. Guinness apparently didn't fit into what the royal family was seeking for Charles' future bride. Sabrina wasn't "tidy," as the Daily Mail reported — she had a well-documented dating history. While that's fine for literally anybody and everybody, it did not fly with Queen Elizabeth II. As Vanity Fair reported, the mentality surrounding Charles' future spouse's virginity was a "cult" way of thinking.

Of her suitors, the Daily Mail noted that Sabrina was seen with the likes of Mick Jagger, Rod Stewart, Jack Nicholson, and politician Jonathan Aitken. Her career as a nursery school teacher had taken her to Los Angeles and back, and she had rubbed shoulders with some of the biggest names in pop culture and entertainment of the 1970s. As such, she was not the "virgin bride" the royals were set on, and she was dumped along with the others.

Unfortunately, Sabrina has often been publicly linked to Charles, as she has been unable to shake the title of "Charles' ex." However, at the age of 59, Guinness did say "I do" — not to Charles, but to dramatist Tom Stoppard (via Daily Mail).

Lady Jane Wellesley could've been the perfect match for Charles

A few years before King Charles III attempted to woo his cousin, another lady was at the center of his desire. As noted by Express, Charles and Lady Jane Wellesley, daughter of the Duke of Wellington, were connected in 1973. Not dissimilar to other women who had come and gone from Charles' life, Jane too came from an upper-class family and was gorgeous to boot. While the two did become more acquainted with time, Jane quickly realized that Charles' heart would never warm to her, as another woman was predominately in his life: Camilla Parker Bowles.

Royal biographer Christopher Wilson explained the situation to Express, saying, "Any pretty woman who was around wanted to be seen on the arm of the Prince of Wales. But pretty soon, they came to the realization of what it was like to live with a man who was in love with somebody else." As far as Jane was concerned, she was an "early example" of what that life — the one that Diana Spencer would later live — was like. "Everybody looked to her as the new Princess of Wales but she saw very early on the shadow of Camilla," Wilson attested.

In 1974, Charles and Jane broke things off, which Jane blamed on the media frenzy that surrounded her. When she was asked point blank if Charles was going to pop the question, she simply said, "Do you honestly believe I want to be queen?"

Camilla's relationship with Charles foiled another girlfriend's fate

King Charles III and Camilla, Queen Consort, met in 1971 at a polo match and were instantly taken with each other. While their time came to an end — as Charles' naval career took off and Camilla was deemed too "experienced" to be his bride — the two never stopped their friendship (nor their affair, some speculate). While writing "The Duchess: The Untold Story," Penny Junor found that when Charles was once again on the dating scene in 1980 — with the intention to find a bride this time — he had just split up with a Scottish heiress named Anna Wallace. Her experience was quite the foreshadowing of Charles' future marriage to Princess Diana.

So, who was Anna? As noted by Express, she was a woman who turned Charles' marriage proposal down not just once but twice (we love a woman who knows what she wants). And as it happened, Charles was simply not the man of her desires and she picked up on clues that he was still seeing Camilla while they were together. "Charles had taken [Anna] to two successive balls and then danced with Camilla for most of both evenings," Junor wrote in her book. "Anna dumped him with the words: 'No one treats me like that — not even you.'" After that breakup, the press and his family were pressuring Charles to get married more than ever. At 32, his bachelorhood was running low on time.

The king dated Diana Spencer's sister, Sarah

If you thought that things were already trippy when it came to King Charles III's dating history, get ready to be thoroughly thrown off. Before he sparked a relationship with Diana Spencer, Charles was romantically connected to Sarah Spencer, Diana's older sister. As noted by Woman & Home, the two crossed paths in 1977 and dated in their 20s. The seriousness of the connection, however, was lacking. Charles was known at the time as a real player, with some headlines attesting that he had dated 20 women in a decade in his attempt to fall out of love with Camilla Parker Bowles.

For her part, Sarah allegedly had gone through "thousands of boyfriends" by the time her path crossed with the now-king's, so any real connection between them seemed futile at best. The real end to the relationship came when Sarah was asked by reported if she would marry Charles in the future, to which she said, "[I wouldn't marry him] if he were the dustman or the king of England." Charles reportedly didn't take the comment particularly well.

Despite their differences and failed romance, Charles and Sarah stayed connected and — you guessed it — Sarah introduced the then-heir to the throne to Diana, her younger sister. While staying at the Spencer home for a hunting trip, Charles met the then-16-year-old Diana — they would become engaged three years later. Of her little sister and Charles' romance, Sarah told The Guardian, "I introduced them. I'm Cupid."

Diana and Charles went on a dozen dates before becoming engaged

Of course, we can't discuss King Charles III's dating history without talking about the Diana Spencer. The "People's Princess" has a legacy that's worth thousands of words, but when she got engaged to Charles, she was a 19-year-old kid who didn't see it coming. As noted by Marie Claire, Charles and Diana had gone out together a total of 12 times — yes, 12 — before he asked her to marry him (via Daily Mail). The Guardian reported at the time that the then-prince was "amazed" that Diana said yes, and even Diana seemed to be completely caught off guard by the proposal.

In the documentary, "Charles and Di: The Truth Behind Their Wedding," royal editor Ingrid Seward shed some light on the moment Charles popped the question, telling viewers that it was more awkward than intimate (via Yahoo). After taking Diana to the nursery — we're a little weirded out by that too — Charles proposed, and Diana "burst out laughing." "I think that was probably just her nerves," Seward said. "She didn't think it was the most romantic of proposals but she had the proposal."

Much like the proposal, the couple's relationship was not the fairytale that many believed it to be. Royal biographer Christopher Wilson later said that after Charles proposed, he called his mother, Queen Elizabeth II, and told her, "There, I've done it now. You've asked me to get married to somebody, and I've fixed it" (via Yahoo).

Charles dated, had an affair with, and finally wed Camilla

Of all the women King Charles III dated, no one, in his eyes, held a candle to Camilla, Queen Consort. The pair dated in the early 1970s before breaking up, marrying other people, and restarting their affair in 1986 (via Brides). They endured leaked phone calls, faced the people and the press, and finally, in 2005, tied the knot. While the public has certainly taken its time to warm up to Camilla, her dedication to the crown has won her some favor, but it's still difficult for the queen consort to compete with Diana Spencer's legacy.

Upon Queen Elizabeth II's death and Charles' ascension to the throne, Twitter was on fire about Diana and made it very clear that the crown should've been Diana's — or that she should've been spared by the royal family all together. "Still team DIANA," one passionate Twitter user wrote. "Diana Spencer, Queen of people's hearts," wrote another. And yet another still attested, "The true QUEEN that never was, she faced it so rough and nobody defended her. She died fighting alone. Her only crime was getting married to a royal."

As reported by YouGov, Charles' popularity in the second quarter of 2022 sat at 42%, while Camilla's popularity was ranked at 40%. The pair are well behind Prince William and Princess Catherine, as well as Princess Anne. Will the couple now finally win over the public? Only time will tell.