Encouraged, reportedly, by his great-uncle Lord Mountbatten "to sow his wild oats", the then Prince of Wales enjoyed a string of romances with more than 20 mostly titled, aristocratic girls – dubbed "Charlie's Angels" by the press – before his marriage to Lady Diana Spencer in 1981. He planned to wed by the age of 30 but acknowledged the challenges of finding a suitable wife.
"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," he said in his first TV interview with the BBC in 1969.
Lucia Santa Cruz
Two years previously, Charles had dated Lucia Santa Cruz, the daughter of a former Chilean ambassador to London, whom he had met at Trinity College, Cambridge. Five years older than Charles, she was "the first real love of his life", according to his biographer Sally Bedell Smith. It's not known why it ended, but Lucia apparently first introduced Charles to Camilla Shand.
Lady Jane Wellesley
The Prince went on to date the daughter of the 8th Duke of Wellington, Lady Jane Wellesley, in 1973, blaming the intense scrutiny of the media when they parted ways a year later. However, when asked if there was going to be an engagement announcement, Lady Jane had snapped: "Do you honestly believe I want to be Queen?"
Davina Sheffield, the granddaughter of the 1st Lord McGowan and cousin of Samantha Cameron, was romantically linked to Charles in 1976, but according to royal author Penny Junor, the relationship was "killed stone dead" when an ex-boyfriend talked about his affair with Davina, after which she was no longer considered a suitable candidate.
Lady Sarah Spencer
The press also played a part in the demise of Charles's brief relationship with Lady Sarah Spencer, Diana's elder sister, in 1977, when she reportedly talked of her royal romance with two reporters, telling them she wouldn’t marry him "if he were the dustman or the King of England". According to sources, the relationship fizzled out shortly after Charles saw the article and told her: "You've just done something incredibly stupid." She later took credit for introducing him to Diana, saying: "I'm Cupid."
The brewing dynasty heiress and It-girl of her generation, Sabrina Guinness, enchanted Charles in 1979. He was said to be besotted with her, to the point where he even took her to Balmoral to meet the family. Princess Margaret described the relationship as "serious", but Charles is said to have brought it to an abrupt end after nine months because the Queen was unhappy about Sabrina's "racy" past. Described as Charles's "liveliest" girlfriend, Sabrina went on to be romantically linked to Mick Jagger, David Bowie and Jack Nicholson, and married the playwright Tom Stoppard in 2014.
Lady Amanda Knatchbull
Still on the hunt for a bride, Charles proposed to Lady Amanda Knatchbull, the granddaughter of Lord Mountbatten and his second cousin, in 1980. According to royal author Robert Lacey, the Prince was "very fond" of her, and "over the years, the two cousins did grow close, developing a mutual respect and friendship that has lasted to the present day". Prince Philip was reportedly very keen for the union to work. It was, however, bad timing. Shortly beforehand, Amanda had lost her younger brother Nicholas and her grandfather in an IRA assassination, and reportedly could not reconcile herself to the idea of being so firmly in the royal spotlight.
Later, Charles would then go onto fall in love with Princess Diana and they married in a spectacular wedding. Revisit some of those show-stopping moments in the video below...
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