Prince Charles once memorably said: ‘I personally feel that a good age for a man to get married is around 30’.
And it was clear he intended to meet this self-imposed deadline.
The future King set about the task with enthusiasm – and a string of close friendships and relationships with princesses, heiresses and even a second cousin until, in 1981, he finally married Lady Diana Spencer.
If some were fleeting romances, other relationships were more serious. Charles had popped the question no fewer then three times by the time he met his first wife.
Famously, there was even a long on-and-off relationship with Camilla Shand, now Queen Consort.
This had originally ended in heartbreak for the prince. He had been away serving with the Royal Navy when, in 1973, he heard that Camilla had become engaged to glamorous Army Officer, Andrew Parker Bowles.
Here, MailOnline takes a look at the long list of the women who might – if only for a moment – have imagined they’d one day be Queen.
Lucia Santa Cruz
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Prince Charles met Lucia Santa Cruz in 1967 at a dinner party hosted by a friend when he was studying at Cambridge University. Pictured: Lucia and Charles leaving the Fortune Theater in London after seeing a performance of The Contractor, a play by David Storey
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Daughter of the Chilean Ambassador to London, Lucia was in Cambridge because she was working for Lord ‘Rab’ Butler, Master of Trinity College Cambridge, where Charles studied
Charles met Lucia Santa Cruz in 1967 at a dinner party hosted by a mutual friend when he was at Cambridge University.
The blonde beauty was the daughter of the then Chilean Ambassador to London. She had been working for Lord ‘Rab’ Butler, master of Trinity, Charles’s college.
They dated for three years until 1970. It is unknown why the relationship ended.
According to Charles’s official biographer, Jonathan Dimbleby, it was Lucia to whom he lost his virginity. She was three years older than him.
Interestingly it was also Lucia who introduced him to his future wife, Camilla Shand, as she was then known.
Dimbleby said Lucia told Charles she had ‘just the girl’ for the young prince and arranged his first meeting with Camilla.
Camilla Shand
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The love story between King Charles and his wife Camilla, Queen Consort began more than five decades ago when they were both in their early 20s
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They had an on-off relationship between 1970 and 1973 when Camilla married Andrew Parker-Bowles in 1973. Pictured: Charles and Camilla following a polo match in 1972
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While Charles was away with the navy, Camilla Shand became engaged to Andrew Parker-Bowles. Heartbroken, Prince Charles reportedly begged Camilla not to go ahead. Pictured: a young Camilla Shand and her mother at her debutant party in Sussex 1965
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Charles and Camilla made their first public appearance together in 1997. They married in 2005 and celebrated their 18th anniversary this year. Pictured here in Caithness in 2004
The love story between King Charles and his wife Camilla, Queen Consort began more than five decades ago.
The pair first met when they were both in their early 20s.
It has been suggested that Camilla had quipped to the future King: ‘My great-grandmother was the mistress of your great-great-grandfather. I feel we have something in common.’
Over the next few years, the pair became romantically involved.
Some royal biographers have suggested Camilla had an ulterior motive – to make her future husband, Andrew Parker-Bowles, jealous.
Known as a ladies man, Parker-Bowles had conducted his own on-off relationship with Camilla – but had been dating other women at the same time, including some of her friends and Charles’s own sister, Princess Anne.
In her book The Duchess: The Untold Story, Penny Junor wrote: ‘There was certainly an element of tit-for-tat in Camilla’s fling with Charles.
‘Indeed, her principal motivation was to have some excitement and make Andrew jealous.
‘She knew the affair with Charles would never go anywhere, could never go anywhere.’
They continued to date on and off until 1973, when Charles was sent away on HMS Minerva as part of his Royal Navy training.
It was while he was away that Camilla became engaged to Andrew Parker-Bowles.
Heartbroken, Prince Charles begged Camilla not to marry Andrew the week before her wedding, wrote Ms Junor.
Throughout the 1980s and 1990s Camilla and Charles remained friends, with royal biographers suggesting it was purely platonic for a time.
Charles became godfather to Camilla’s son, Tom.
In 2003 the couple moved into Clarence House together before getting married in 2005. They celebrated their 18th anniversary this year.
Lady ‘Kanga’ Tryon
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Prince Charles and Australian beauty Dale ‘Kanga’ Tryon grew close when he was in his twenties. The two remained friends and are seen here attending a ball in 1990
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Prince Charles and Lady Tryon at a 1991 polo match. The two first met when he was just 17 and briefly studied at Geelong Grammar School in Australia. Born Dale Harper to a Melbourne printing mogul, Dale became Lady Tryon after marrying a close associate of Charles
In 1966, a 17-year-old Charles spent two terms studying at at Geelong Grammar School in the Australian state of Victoria.
This is where he first met Dale Harper, daughter of a wealthy Melbourne printing mogul.
Some years later, she moved to Britain to become a PR officer for Qantas airlines. She also became the wife of the banker Anthony Tryon, third Baron Tryon, an associate of Prince Charles.
In the early 1970s, around the same period he was seeing Camilla, Lady Tyron – nicknamed ‘Kanga – was also in the picture.
Charles was said to have described her as ‘the only woman who ever understood me’, but some suggest claim is thought to have begun with Kanga herself.
Sadly Lady Tyron died just a few months after Princess Diana.
Lady Jane Wellesley
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Charles had known Lady Jane Wellesley, the only daughter of the Duke of Wellington, since childhood. Many thought she was in a good position to become Charles’s bride. The two are pictured here in 1977
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When reporters and photographers camped outside Lady Jane’s small terraced house in Fulham, she supposedly said: ‘Do you honestly believe I want to be Queen?
After his old flame Camilla Shand married Andrew Parker Bowles in July 1973, Charles moved on.
The next subject of his attention 22-year-old Lady Jane Wellesley, the only daughter of the Duke of Wellington. Charles had known Jane since childhood.
At the time, many suggested she was in a good position to become Charles’s bride.
The rumour mill really got going when Charles flew out to Spain to join the Wellingtons on a shooting holiday.
At the time, Lady Jane denied there was any romance, stating that the two were ‘just good friends’.
Few believed her, however. Photographers and reporters camped outside her small terraced house in Fulham and 10,000 people jammed the Norfolk roads around Sandringham during the New Year’s Eve festivities in an attempt to see the woman who could be the country’s future Queen.
She did not enjoy being in the royal spotlight, reportedly saying to Charles: ‘I don’t want another title — I’ve already got one, thank you.’
After being questioned over the couple’s (supposed) impending engagement, she once snapped back, according to Tatler: ‘Do you honestly believe I want to be Queen?’
Davina Sheffield
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After Prince Charles and Camilla broke up, he began seeing 5ft 10in blonde Davina Sheffield
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Charles was so smitten with Davina he invited her to Balmoral for the weekend. She even earned the approval of the Queen Mother. Pictured: Charles and Davina in 1979
Following the end of his earlier relationship with Camilla, Charles was eager to be married before 30.
He began dating Davina Sheffield, a 5ft 10in blonde with a beautiful smile.
She was a cousin of Samantha Sheffield, who went on to become the wife of the former Prime Minister David Cameron.
Charles was smitten with Davina, so much so that he invited her to Balmoral for the weekend.
A friend told The Daily Mail at the time: ‘She and Charles were wonderful together.’
Davina even earned the approval of the Queen Mother.
But their relationship was thrown off course when an ex-boyfriend, powerboat racer James Beard, revealed that he had lived with Davina before she started dating Charles.
This brought their relationship to an abrupt end as royal tradition suggested that Charles would need to marry an ‘unblemished’ bride.
Susan George
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On the night of Charles’s 30th birthday in 1978, he danced with actress Susan George. Candle-lit dinners and theatre trips followed. Pictured: Charles and Susan in 1993
Susan George is an English film and television actress who shot to fame when she starred in the 1971 thriller Straw Dogs.
Susan had been one of 400 guests to join Charles’s 30th birthday bash at Buckingham Palace.
During the night they were pictured dancing together, which led to a brief romance of candlelit dinners and trips to the theatre, the Daily Mail diary editor reported at the time.
Susan is now a professional horse breeder.
Rosie Clifton
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Rosie Clifton and Prince Charles dated for a brief period in the 1970s. She went on to marry the brother of Lord ‘Spam’, Mark Vestey. Pictured: Prince Charles and Rosie Clifton
Rosie Clifton and Prince Charles dated for a brief period in the 1970s.
She went on to marry the brother of Lord ‘Spam Vestey’, Mark Vestey.
Princess Marie-Astrid of Luxembourg
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In June 1977, the Daily Express published a front page report stating that ‘Prince Charles is to marry Princess Marie Astrid of Luxembourg’
In June 1977, the Daily Express was confident that ‘Prince Charles is to marry Princess Marie Astrid of Luxembourg’ – and put it on the front page.
Marie was the daughter of the Grand Duke of Luxembourg and Princess Josephine Charlotte, daughter of the former King Leopold and Queen Astrid of Belgium.
At the time she was considered to be one of the only eligible Princesses in Europe.
The Express reporter wrote: ‘The formal engagement will be announced from Buckingham Palace next Monday.
‘The couple’s difference of religion – she is a Roman Catholic – will be overcome by a novel constitutional arrangement: any sons of the marriage will be brought up according to the Church of England while daughters will be raised in the Catholic faith.’
The piece said that the Queen and Prince Phillip had ‘assented to this procedure, which also has the approval of Church leaders’.
However, the scoop was untrue.
Indeed, the final line of the story read: ‘Last night Buckingham Palace denied there was to be an announcement of an engagement.’
The prince had only seen the princess briefly at his investiture as Prince of Wales in 1969 and then again briefly in his university days.
The rumours led Charles to authorise a Palace press statement, which said: ‘They are not getting engaged this Monday, next Monday, the Monday after or any other Monday, Tuesday, Wednesday or Thursday.
‘They do not know each other, and people who do not know each other do not get engaged. The Royal Family do not go in for arranged marriages.’
Caroline Longman
Caroline Longman was the goddaughter of the late Queen Elizabeth and daughter of the publisher Mark Longman. Charles and Caroline are seen here at Windsor Great Park in 1979
Charles relationship with Caroline Longman, daughter of publisher Mark Longman and granddaughter of the 10th Earl of Cavan, was a fleeting affair.
The pair were thought to be an item for a brief time in the 1970s. They had been pictured together at polo matches and n his Aston Martin.
Caroline was a goddaughter of Queen Elizabeth.
Caroline’s mother, Lady Elizabeth Longman, was close friends with The Queen and had been one of her bridesmaids in 1947.
Bettina Lindsay
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Lady Bettina Lindsay dated Prince Charles in the 1970s, before he met Princess Diana. On one occasion they were spotted attending a play together. Pictured: Charles and Bettina (left) leave the Savoy Theatre together after seeing The Secretary Bird
Lady Bettina Lindsay dated Prince Charles in the 1970s, before he met Princess Diana.
On one occasion they were spotted attending the Savoy Theatre for a production f The Secretary Bird, a comedy by William Douglas-Home, playwright brother of former Prime Minister Alec Douglas-Home.
Georgiana Russell
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The prince was said to have had a brief fling with Georgiana Russell, daughter of former Ambassador Sir John Russell. In her book Diana, the biographer Sarah Bradford’ writes that Georgiana ‘got fed up with standing in cold Scottish rivers’ and married someone else
The prince was said to have a brief fling with Georgiana Russell, daughter of the former Ambassador Sir John Russell.
There is little information, nor photos, of their relationship but in Sarah Bradford’s biography of Diana she wrote that Georgiana ‘got fed up with standing in cold Scottish rivers and married someone else’.
Lady Sarah Spencer
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In 1977, before he married Diana Spencer, Charles dated her older sister, Lady Sarah. Ahead of the 1981 wedding, Sarah said: ‘I introduced them. I’m cupid.’
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On holiday in the Swiss ski resort of Klosters, Lady Sarah Spencer shut down rumours, telling reporters it was a ‘marvellous holiday but there’s no question of an engagement’
Before he married Diana Spencer, he dated her older sister, Lady Sarah in 1977.
For a while, Lady Sarah became the centre of speculation surrounding Charles’s engagement plans.
But those rumours were put to an abrupt end in 1978 while she was on a ski trip with the Prince in the Swiss resort Klosters.
She told reporters it was a ‘marvellous holiday but there’s no question of an engagement’.
According to Time magazine, Lady Sarah said: ‘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.’
It was during a shooting party the same year at the Spencer’s Althorp estate in Northamptonshire that 29-year-old Charles met 16-year-old Diana.
Ahead of Charles and Diana’s wedding, in 1981 Sarah said: ‘I introduced them. I’m cupid.’
Sabrina Guinness
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Sabrina was an heiress to the Guinness brewing dynasty. Pictured: Charles and Sabrina at a polo match at Windsor Great Park during August 1979
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Sabrina Guinness thought of as an ‘it’ girl. Very beautiful, she boasted long legs and a bright mind. Sabrina remained single for 34 years until she married playwright Sir Tom Stoppard, 17 years her senior, in 2013.
Sabrina Guinness was believed to be the ‘it’ girl of her generation, a beautiful woman with long legs and a bright mind.
She was a Guinness heiress thanks to her father, James Guinness, who worked on the banking side of the billionaire brewery firm.
It was first speculated that Charles and Sabrina might be more than friends when they attended the musical Ain’t Misbehavin’.
In 1979 they were seen fishing, riding and shooting together. She was said to be the ‘liveliest’ of Charles’s fancies.
It all came to a crashing end, however, when Sabrina allegedly failed the so-called ‘Balmoral Test’.
The Queen was displeased that she had decided to sit in Queen Victoria’s chair and was snubbed by Prince Philip.
Upon arriving at Balmoral, the heiress joked that the transport bringing her to the castle was like a Black Mariah – a type of police van.
Unamused, the Prince snapped back: ‘Well, you’d know all about Black Mariahs, wouldn’t you?’
The relationship failed to flourish after this rocky start, leading them to break up nine months into their courtship.
Sabrina went on to date countless A-listers from all over the world, including Mick Jagger, Paul McCartney, Michael Douglass and Rod Stewart.
She remained single for 34 years until she married the playwright Sir Tom Stoppard, 17 years her senior, in 2013.
Jane Ward
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Prince Charles briefly dated Jane Ward in 1979. The two were seen together at polo parties
In 1979 Prince Charles briefly dated Jane Ward. They were seen together at polo parties, with claims he once seduced her in the bushes.
They also enjoyed the ‘privacy of her secluded cottage in Windsor’, Rhe Daily Mail has previously reported.
Lady Amanda Knatchbull
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Charles had proposed to Lady Amanda Knatchbull before he married Diana. As second cousins, the pair had known each other for a long time. Her grandfather was Lord Mountbatten, who was Prince Philip’s maternal uncle and particularly close to Charles
Lady Amanda Knatchbull was another woman to whom Prince Charles had proposed.
As second cousins, the pair already each other through her grandfather, Lord Mountbatten, who was Prince Philip’s maternal uncle, and close to Charles.
Before his death, Lord Mountbatten had encouraged Charles’s to propose to Amanda.
While dating, they were seen in the Bahamas together.
In his 2007 biography, Charles – The man who will be King, wrote how fond Lady Amanda was of the future monarch.
He said: ‘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.’
In 1980, having passed his self-ordained deadline to be married by 30, Charles proposed to Amanda.
Less than a year earlier, Amanda had lost her younger brother, Nicholas, and her beloved grandfather Lord Mountbatten in an IRA assassination on August 27 1979.
In Robert Lacey’s book, Battle of the Brothers, he explained: ‘Over the years the two cousins did grow close, developing a mutual respect and friendship that has lasted to the present day.
‘But when the prince finally made his proposal in the summer of 1979—shortly before Lord Mountbatten’s assassination by the IRA—the independent-minded Amanda politely turned him down.’
‘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’.
Anna Wallace
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Anna Wallace, daughter of a wealthy Scottish landowner, became known as the woman who Charles unsuccessfully proposed to twice – unsuccessfully
Anna Wallace became known as the woman who Charles proposed to twice.
The daughter of wealthy Scottish landowner Hamish Wallace, Anna was dubbed by the press ‘Whiplash’ because of her fearless attitude and great horsemanship.
In 1980 the couple started dating but after a year the relationship ended following a furious row at a ball to honour the Queen Mother’s 80th birthday.
She had largely been ignored by Charles during the event, Tatler reported. Not only that, the Prince of Wales had spent much of the night dancing with former lover Camilla Parker Bowles.
It was reported at the time that she had shouted: ‘I have never been so badly treated before in my life. No one treats me like that.
‘Not even you.’
