The Crown: Prince Charles’s dating history, from Camilla to Princess Diana’s sister

The fourth season of The Crown delivers an in-depth look at some of the most momentous moments in the public and private lives of the royal family.

The new series begins as the 1970s are drawing to a close, during which time the Queen is focused on preserving the line of succession by finding an appropriate bride for Prince Charles, who was still unmarried at the age of 30.

Josh O'Connor returns to the new series as Prince Charles and Emerald Fennell is back as Camilla Parker Bowles,  while Emma Corrin  makes her anticipated debut as Princess Diana.

While Camilla and Diana are considered to be the most significant love interests of the prince, Charles was not short of admirers during his youth, which season four shows.

Between meeting his first girlfriend while studying at Trinity College in 1967 and marrying Lady Diana Spencer in 1981, the Prince of Wales was romantically linked to a number of women.

At the urging of his uncle, Lord Louis Mountbatten, who served as a father figure for the future King, Charles did not hold back during his twenties and reportedly dated more than 20 women in the space of a decade.

According to Netflix documentary The Royal House of Windsor, Mountbatten wrote a letter to Charles in 1974, encouraging him to “sow his wild oats”.

“In a case like yours, the man should sow his wild oats and have as many affairs as he can before settling down,” he wrote. “But for a wife, he should choose a suitable, attractive and sweet-charactered girl before she met anyone she might fall for.”

The 1970s were a trying time for the prince as, under pressure from the royal family and public opinion, he attempted to find a wife deemed “suitable”. 

During his first ever TV interview with the BBC that same year, Charles opened up about the importance of choosing the right partner, stating: “This is obviously very difficult because you’ve got to remember that when you marry, in my position, you’re going to marry somebody who, perhaps one day is going to become queen.

“You’ve got to choose somebody very carefully, I think, who can fulfil this particular role, because people like you, perhaps, would expect quite a lot from somebody like that, and it’s got to be somebody pretty special.”

In his search for that special someone, biographer Christopher Wilson said the prince had “a string of arm candy” adding that, while he fell deeply in love with a handful of partners during his younger years, many were women he would “take out simply because it made him look good.”

So, who were the women that did not quite make the cut? From sprigs of aristocracy to actors and Princess Diana’s older sister, here we take a look at some of Prince Charles’s many girlfriends over the years.

Lucia Santa Cruz

Lucia Santa Cruz, who is the daughter of the former Chilean ambassador to London, is said to have had a brief but passionate romance with Prince Charles some 40 years ago when he was studying at Cambridge University.

Shortly after joining Trinity College in 1967, Charles met Lucia, who was five years his elder, at a dinner party hosted by a mutual friend.

According to biographer Sally Bedell Smith, Charles’ cousin Lady Elizabeth Anson, who was also a friend of Lucia’s, commented: “She was the first real love of his life”.

Ironically, it was Charles’s first love who introduced him to the great love of his life. In his authorised biography of the Prince of Wales, author Jonathan Dimbleby says Lucia told Charles she had “just the girl” for the young prince and subsequently arranged for the royal to meet Camilla Shand — later Parker Bowles.

Lucia has remained close to Charles and Camilla. In 2009, when the prince and the Duchess of Cornwall embarked on an official tour of South America, they visited her in Lima. then, in 2011, she was invited to the Duke and Duchess of Cambridge’s wedding.

Camilla Shand

Prince Charles and Camilla Parker Bowles's relationship has made headlines from the very beginning.

According to the biography Charles and Camila: Portrait of a Love Affair by Gyles Brandreth, the two reportedly first met in 1971. While it is widely believed that Charles and Camilla met at a polo match in 1972, Brandreth wrote that they were actually introduced by their mutual friend, Lucia Santa Cruz.

The two quickly started dating but broke up before Charles left to serve in the Royal Navy. When he returned eight months later, Camilla was engaged to her on-again-off-again boyfriend, Andrew Parker Bowles, whom she went on to marry in 1973.

In 1981, Charles married Diana Spencer but, he began an affair with Camilla five years later. In 1994, Charles admitted to committing adultery during his marriage in an interview with Jonathan Dimbleby. When asked if he tried to be “faithful and honourable" to Diana, Charles initially replied: “Yes, absolutely,” but when prompted further by Dimbleby, the prince added: “Yes… until it became irretrievably broken down, us both having tried.”

In December 1993, prime minister John Major announced that Charles and Diana had officially separated and two years later, so did Camilla and Andrew.

Following the death of Diana in 1997, Charles and Camilla rekindled their relationship but were not photographed together until 1999.

It wasn’t until 2003 that the couple moved in together at Clarence House residence, before announcing their engagement in February 2005. Charles proposed with an art deco-style ring that features a five-carat emerald cut diamond in the centre and three diamond baguettes on each side. The ring belonged to his grandmother, the Queen Mother.

On 9 April 2005, Charles and Camilla got married in a civil ceremony. Prince William served as the best man, and Camilla's son Tom was a witness. Queen Elizabeth II and Prince Philip didn't attend the ceremony but did make an appearance at the Service of Prayer and Dedication at St George's Chapel.

Lady Jane Wellesley

Daughter of the 8th Duke of Wellington, Lady Jane Wellesley reportedly had a courtship with the Prince of Wales in her early twenties and was considered by many to be a prime candidate for marriage.

The couple were together between 1973 and 1974 and when they eventually parted ways, blame was put on intense media scrutiny. 

When asked on one occasion if there was to be an engagement announcement, Jane said: “Do you honestly believe I want to be Queen?”

Davina Sheffield

The granddaughter of 1st Lord McGowan and cousin of Samantha Cameron, Davina Sheffield was romantically linked to Prince Charles in 1976.

In her 2005 book The Firm, author Penny Junor delved into the romance, which she said was “killed stone dead” after an ex-boyfriend of Davina’s spoke to the press.

“In 1976, the prince fell for another girl, Davina Sheffield, who could have been the soulmate he was searching for,” Junor wrote.

“She seemed ideal in so many ways, and they appeared to be very much in love but she already had a boyfriend when Charles met her, an Old Harrovian and powerboat racer named James Beard.

“He was subsequently conned into talking about his relationship with Davina by what turned out to be a Sunday tabloid reporter and the story of their affair, complete with photographs of their ‘love nest’, made headline news.”

The admission meant that Davina was no longer considered a suitable wife, as royal brides were at that time expected to still be virginal by the time they walked down the aisle. This was exactly the same obstacle which had prevented Charles from settling down with Camilla a few years before.

Lady Sarah Spencer

Daughter of 8th Earl Spencer and elder sister to Princess Diana, Lady Sarah Spencer briefly dated Prince Charles in 1977. But, after she spoke about their relationship in the press, the two split.

While it sounds strange that her own sister started seeing Charles after they broke up, Sarah took pride in the fact that she set the two of them up. 

“I introduced them,” she once said. “I’m Cupid.”

Lady Amanda Knatchbull

After his relationship with Sarah Spencer came to an end, Charles resumed his search for a suitable bride and, in 1980, proposed to Lady Amanda Knatchbull, the granddaughter of Lord Mountbatten.

Writing in his 2007 biography Charles: The man who will be King, Howard Hodgson explained how Amanda had become fond of the Prince of Wales.

“She was equally impressed with his energy, enthusiasm, sense of fun, kindness and modest self-deprecation,” he wrote.

“She was indeed a very sensible and loving girl, who genuinely did share all the same interests as the heir to the throne.”

Amanda turned Charles’s proposal down, citing the glare of the royal spotlight.

Anna Wallace

Having passed his self-ordained deadline of the age of 30 to get married, Charles remained undeterred and proposed to Anna Wallace, the daughter of a Scottish landowner, later that same year.

In the book The Duchess of Cornwall: Camilla Story and Secrets, author Jessica Jayne claimed that Anna broke off their relationship during the Queen Mother’s 80th birthday party because Charles had ignored her all evening.

However, in her 2017 book The Duchess, Junor stated that the two actually parted ways due to the prince’s relationship with Camilla.  

“Charles had taken her to two successive balls and then danced with Camilla for most of both evenings,” Junor wrote. “Anna dumped him with the words: ‘No one treats me like that – not even you.’”  

The couple had only just broken up when Charles met Diana in the summer of 1980.

Lady Diana Spencer

Diana and Prince Charles initially met through her older sister, Sarah, in 1977, when she was just 16 years old and he was 28.

Recalling their first meeting, Prince Charles said in an interview conducted in 1981 that he could “remember thinking what a very jolly and amusing and attractive 16-year-old she was”, describing her as “great fun, and bouncy and full of life”.

The two next met in 1980, a year after the assassination of Lord Mountbatten and, in a private tape released in the documentary Diana: In Her Own Words, Diana can be heard saying that she sympathised with how “lonely” Charles must have been feeling at the time.

It soon became apparent that Prince Charles was considering Lady Diana Spencer as his bride when she was invited to spend some time with the royal family at Balmoral in November 1980, and in February 1981, the couple announced their engagement.

During a television interview to share the news, an interviewer behind the camera asked the couple: "Are you in love?". While Diana immediately replied with a giggle, “Of course”, Charles added: "Whatever ‘in love’ means." 

After six months, they were married in a lavish ceremony at Westminster Abbey, described by many as the “wedding of the century”. The couple went on to have two children – Prince William and Prince Harry – however, their relationship was not meant to be.

In 1986, Prince Charles began an affair with Camilla Parker Bowles, according to his official biographer Jonathan Dimbleby, while Diana also admitted to being unfaithful in the marriage with James Hewitt – a former household cavalry officer in the British Army.

Six years later, then-prime minister John Major announced that Charles and Diana were separating and their divorce was finalised in 1996. 

Just one year later, Diana was killed in a car crash in Paris alongside her partner, Dodi Fayed, and their driver, Henri Paul.

You can read more about the story of Charles and Diana’s first meeting here.