Princess Diana Would Not Have Married Prince Charles If One of These Women Had Accepted His Marriage Proposals

King Charles was once the most eligible suitor before marrying Lady Diana. However, not many know that even the future King had to try a few times before finding someone to marry him, even proposing to his cousin.

Numerous fairy tales follow the storylines of princesses who must go through several suitors before finding their soulmates. However, it seems as if the storybooks have got it all wrong as things are the other way around.

The entire world knows of King Charles' love triangle, but not many know of the other pursuits he thought would be his wives. It turns out even the future King has to kiss a few maidens before finding the one.

King Charles was born into one of the most powerful families globally, so finding a wife for him seemed effortless from the outside. However, things were not as simple as we thought for the throne's heir.

The Queen's first-born son is now King, but it seems not many women were waiting in line to marry him during his younger years. As a result, the then-Prince's search for a bride turned out to be longer than expected.

It is global knowledge that Lady Diana sought a divorce from then-Prince Charles after years of an unhappy marriage. However, the divorce was surprisingly not the first or second time the heir had been dumped.

Charles famously fell in love with Camilla Parker Bowles a year after meeting her in the summer of 1971. Camilla was dating Andrew Parker Bowles at the time. However, he was often away due to his army service.

Although then-Prince Charles and Bowles fell for each other, their lineage got in the way of their relationship. Bowles was born from a well-off family; however, she wasn't an aristocrat and wasn't "pure," making their union impossible.

The then-Prince eventually sailed off with the Royal Navy in 1973, and Bowles was engaged a few months later. Then-Prince Charles' first potential soulmate was then married in July that year, leaving the heir alone.

Thankfully, Charles was free to explore romance however he liked, and so he carried on his quest for love. He was linked to many beautiful women after Bowles, with reports claiming he had dated twenty women.

As then-Prince Charles approached 30, he started to consider marriage for himself seriously. He set his eyes on Davina Sheffield, who ticked all of the boxes for a potential royal bride, except for one thing. Royal watchers at the time even called her his "soulmate," and Tatler described her romance with Charles as so profound that she was considered a future queen.

Charles and Davina were first linked in 1976, and were often seen together at society events. She even travelled with him to Balmoral to meet his family, winning the approval of the Queen Mother. On one occasion, Davina was seen sitting with the late Queen and Prince Philip at an equestrian event.

However, their romance was "killed stone dead" when Davina's ex-boyfriend, powerboat racer James Beard, went public with their former romance and "love nest." At the time, royal convention dictated that Charles choose an "unblemished" bride, bringing their relationship to a sudden end.

Davina was the granddaughter of the 1st Lord McGowan, who previously served as the Chairman of Imperial Chemical Industries, and she was also the cousin of Samantha Cameron. She was known for her charitable work, even travelling to Vietnam to briefly work in an orphanage as the Vietnam War drew to a close.

Davina passed away on 2 September 2026 at the age of 75, following a short illness, with her three sons, Tom, Billy, and Henry, confirming her passing. A celebration of her life is being planned for 2 November.

Things seemed to take a turn for the best when Lady Amanda Knatchbull caught the Prince's eye. Lady Knatchbull is Charles' second cousin, making her eligible for the marriage; however, she rejected the proposal.

Lady Knatchbull could not handle the scrutiny of being part of the royal family after suffering two major losses. Unfortunately, the appeal of Lady Knatchbull among the royals made her the one that got away for the Prince.

Then-Prince Charles later reportedly unsuccessfully proposed to Anna Wallace twice. However, those two rejections were not the worst Prince Charles had to endure from Wallace, who was known for her fiery temper.

The pair reportedly broke up after Prince Charles, who is now King Charles, brought Wallace to two balls and danced with Camilla for most of them. Royal author Penny Junor explored the break up in a book, revealing Wallace's alleged final words to the Prince:

"Anna dumped him with the words: 'No one treats me like that – not even you.'"

Wallace was Prince Charles' last girlfriend before he proposed to one of his ex's younger sisters. Finally, someone folded to the Prince's quest for marriage, and it was 19-year-old Lady Diana Spencer.

The press reported that 750 million people tuned in to watch the couple's extravagant wedding. Prince Charles and Lady Spencer went on to have two children, Prince William and Harry, before divorcing due to the Prince's affair with Bowles.