While Camilla, Duchess of Cornwall, has always held his heart – even throughout his ill-fated marriage to Diana, Princess of Wales – in his youth Prince Charles had a romantic past that was more Hollywood leading man than stuffy British royal.
WATCH BELOW: Prince Charles admits to being unfaithful in his marriage to Diana
Indeed, well before his engagement to Diana Spencer, Charles was even given the nickname “Playboy Prince” by the press, with some reports suggesting he dated about 20 women in 10 years.
Certainly, between 1968 while he was a student at Trinity College, Cambridge, to mid-1980 when he first started dating Diana, there is no doubt that Charles was actively looking for love.
The future king was reportedly advised by his great-uncle Lord Mountbatten to “sow his wild oats and have as many affairs as he can” while he was young, and there was no doubt that Charles made the most of his bacherlorhood – taking his love quest very seriously.
His long string of romances resulted in his girlfriends being dubbed “Charlie’s Angels” by the media, and even his friends and family joined in with the jokes; Lord Mountbatten telling reporters that Charles was constantly “popping in and out of bed with girls”.
Charles’s romantic prospects were made more complicated by his desire to get married by the time he was 30, and the fact that as heir to the throne, he had some strict rules to abide by in order to choose his bride and settle down.
In a 1969 interview, Charles spoke about the huge pressure his future role put him under, explaining, “You’ve got to remember when you marry, in my position, you’re going to marry someone who perhaps one day will 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.”
Lord Mountbatten, too, acknowledged that the royal bride would need to
be a particular kind of girl. “For a wife, he should choose a suitable, attractive and sweet-charactered girl before she met anyone she might fall for,” he wrote.
In 1969 Charles dated Lucia Santa Cruz, the beautiful and brainy daughter of the Chilean ambassador. Sadly, that didn’t work out, and two other short-lived romances followed: one with Sibylla Dorman, daughter of the Governor-General of Malta, then Cindy Buxton, who went on to be a wildlife documentary-maker.
By 1971, of course, he had actually met the true love of his life – Camilla Shand – but their relationship was sadly not permissible at the time.
Royal expert and author Penny Junor said Charles “had the closest relationship with Camilla” and he “really, really loved her”, but Camilla’s party girl background was frowned upon by the royal family – with the heir expected to marry someone with no past.
According to reports Charles was “absolutely heartbroken” when he had to end his relationship with Camilla.
To try and move on, he spent eight months of 1973 with the navy, writing to Lord Mountbatten, “I suppose I shall eventually get over it.” And he had little choice – in July of that year she married Andrew Parker Bowles.
A couple of years later, amid the news of his sister Princess Anne’s engagement, a stoic Prince Charles wrote in a letter to a friend: “I can see I shall have to find myself a wife pretty rapidly, otherwise I shall get left behind and feel very miserable.”
A string of failed romances followed in quick succession.
Charles began seeing Lady Jane Wellesley, daughter of the 8th Duke of Wellington, near the end of 1973, and the pair had a fairly serious relationship, but blamed their break-up on intense media scrutiny.
Indeed, when asked if there was to ever be an engagement announcement, Jane replied, “Do you honestly believe I want to be queen?”
The prince wasted no time continuing his search for love and went on to first date Lady Sarah Spencer (one of Diana’s older sisters), then brewing heiress and “It” girl Sabrina Guinness, with whom he was said to be smitten.
Princess Margaret described their relationship as “serious”, but Charles dropped her like a stone after nine months as the Queen was said to be unhappy with her “racy” past.
There were dates, too, with celebrities such as actress Susan George, Sheila Ferguson of soul trio the Three Degrees and even, it’s rumoured, Barbra Streisand! None of which led anywhere.
There were also marriage proposals along the way.
Charles is said to have first popped the question to Lord Mountbatten’s granddaughter Amanda Knatchbull. While the Queen was allegedly keen on the pairing, Amanda knocked him back, citing the unrelenting glare of the royal spotlight for her reticence.
Charles also proposed twice to wealthy heiress Anna Wallace (nicknamed “Whiplash Wallace” for her temper) in early 1980 but she turned him down both times.
Author Jessica Jayne claimed that Anna broke off their courtship during the Queen Mother’s 80th birthday party after Charles had ignored her all evening, but Penny Junor blamed his love of another woman for the split.
“Charles had taken her to two successive balls and then danced with Camilla for most of both evenings,” she wrote. “Anna dumped him with the words: ‘No-one treats me like that – not even you.’ ”
Then came Diana Spencer.
Charles had first met her back in 1977 when she was a 16-year-old schoolgirl and he was dating her sister. Now it became apparent that Charles was considering Diana as his wife – she was invited to spend time with the royals at Balmoral in November 1980.
While he was said to still be deeply in love with Camilla, the pair wed in 1981, Charles appearing to finally settle down (at least publicly) with a woman both he and his family saw as a “perfect” fit.
But as we now know, it was anything but simple, even then…
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