The story of Prince Charles and Diana’s whirlwind romance seemed like a fairytale come to life – at least it did at first. Behind the scenes, things were very, very different. It took us a while to find out, but it seems Charles and Diana’s marriage might have been doomed not long after it started. And the origins of that breakdown might be pinpointed to a single event – and one very bad joke by Prince Charles made at Diana’s expense.
A very ill-advised joke
Princess Diana had a rough time when she was pregnant with her first son, Prince William. As the first royal placed under a microscope by the press and public, it got so “unbearable” that she eventually had to be induced.
She later added bitterly she needed to find “a date where Charles could get off his polo pony” for her to give birth. Early bad feelings aside, William was born and not long thereafter, Diana found herself pregnant again. It was at the end of this pregnancy, with the baby who would be Prince Harry, that Charles made a quip that broke Diana’s heart – and contributed to their marriage falling apart.
Holding on to her secret
As we’ve mentioned before, despite what she’d gone through while pregnant with William, Diana soldiered on and learned that she was pregnant again in early 1984. After having a boy, Diana knew her husband “desperately” wanted a girl. In fact, she was quoted as saying in the controversial tell-all Diana: Her True Story that Charles had really always wanted two children – a boy and a girl.
Unfortunately, the pregnancy was once again difficult, and Diana reportedly half-joked, “I don’t think I’m made for the production line.” It was possibly made that much harder by the fact she kept the baby’s gender a secret from Charles the entire time. And since she didn’t tell him, he only found out when she gave birth…
Feeling the pressure to produce a ‘spare’
It wasn’t just about Charles’ longstanding desire to have two children, you see. There are many perks that come with being a member of the Royal Family – fame and fortune immediately come to mind. As cushy as their existence might sound, nothing’s ever free. And royal existence, lavish though it is, also comes with a price.
Anyone can notice the constant attention from fans and paparazzi, but some prices are less noticeable, like having to conform to Royal Family norms. One of those norms is the “heir and a spare” mentality. In other words, every firstborn should have a “spare,” in case something bad happens. That was doubly important in Charles’ case, as he’d one day sit on the throne.
Nine hours of labor
And so, with pressure from both her husband and the entire institution of the Royal Family, Princess Diana succeeded in conceiving again in 1984. Fast forward to nine months later, in September, and she gave birth to a baby boy, Henry Charles Albert David Mountbatten-Windsor – but everyone would just call him Harry! As over the moon as she was, Diana was forced to go through incredible hardships during labor.
You know the saying “Difficult pregnancy, easy birth”? Well, in her case, it definitely didn’t hold water. Diana chose not to receive any medication to help her with the pain, or with speeding the process along, making the whole thing last nine hours. And that wasn’t even the worst of it.
Breaking Diana’s heart
Harry’s birth ended up being traumatic for his mom. First, naturally, were the nine hours of pain and suffering. But second, and possibly no less wounding, were her husband’s first remarks upon seeing his new son. Charles, she recalled, looked at Harry with “dismay.”
His first comment was allegedly, “Oh God, it’s a boy.” His second? “And he’s even got red hair.” Not only was he disappointed it was a boy, then, but Diana’s older sisters and younger brother all had red hair. It was a dig not only at her, but at her entire family! Her heart broke.
Their marriage ‘went bang’
In the months that followed, it seemed like Charles had a hard time letting go of the fact he’d gotten another son. In Harry’s christening in December, he reportedly told Frances, Diana’s mother, “We were so disappointed – we thought it would be a girl.”
In the weeks before Harry was born, Diana said she and Charles were “the closest we’ve ever been and ever will be.” Following the birth, however, their marriage “went bang,” going “down the drain.” And things were only made worse by Charles rekindling an old flame.
Going back to Camilla
Diana admitted that after giving birth to Harry, something inside her had closed off. This may or may not have had something to do with the fact Charles had once again resumed his romance with Camilla Parker Bowles. As Diana herself put it, “I knew Charles had gone back to his lady.”
Having first met Camilla in 1970, Charles maintained an on-again, off-again relationship with her for years. It ended when he went overseas with the Royal Navy, and she married another man. However, that allegedly didn’t stop them from carrying on their affair in the years that followed.
Overcoming her fear to confront Camilla
While Charles and Camilla were going about their illicit liaison very carefully, Diana was eagle-eyed enough to see the signs. In fact, it was allegedly during their own honeymoon that Diana found photos of Camilla in Charles’ journal. Years later, in 1989, the notoriously shy royal had had enough. Crashing a birthday party for Camilla’s sister, to which she wasn’t even invited, Diana marched right up to to her husband’s lover.
Despite admitting to being “terrified,” Diana told her she knew everything. Unfazed, Camilla replied that Diana had everything she ever wanted – all the men loved her, and she had two beautiful boys. “What more do you want?” she wondered. “My husband,” Diana answered bitterly.
The writing was on the wall
Charles’ romantic history might’ve hinted at the fact he a hard time staying away from Camilla. The woman he was involved with between Camilla and Diana, in fact, dumped him for that very reason. In the late 1970s, Charles was linked to Anna Wallace, known as “Whiplash Wallace” in royal circles for her fiery attitude.
Wallace even turned down Charles’ marriage proposal – twice! Then, in 1980, after Charles had taken her to two successive balls only to dance with Camilla for most of the night, she’d had enough. “No one treats me like that,” Wallace reportedly said, “not even you.” And she dumped him.
The joke that made Charles fall in love with Camilla
While Charles’ attempt at cracking wise wasn’t appreciated by Diana, it was actually pretty ironic to find out that it was humor that brought him and Camilla together for the first time. It all goes back to the pair’s very first meeting, which took place at a polo match, because where else would it be?
The royal and the commoner connected first over their shared love of the sport. Then, they connected over their shared sense of humor. Camilla’s great-grandmother had had an affair with King Edward VII, an ancestor of Charles. “I feel we have something in common,” she quipped.
The couple that might have been
For a time, it did seem like Charles was destined to marry Camilla eventually. Their romance began in the early 1970s, as we’ve said, but ended abruptly when Charles shipped out overseas. It’s unclear to this day why exactly that happened, but they resumed their love affair after Camilla’s marriage to British army officer Andrew Parker Bowles.
If royal experts are to be believed, Camilla’s husband knew about his wife’s indiscretion – he simply didn’t care. However, as much as they may have wanted to make it official, the Queen was said to have nixed any union with Camilla.
Charles married Diana on the advice of two married women
The fact Charles ended up marrying Diana, then, was possibly less than a foregone conclusion. And Camilla’s fingerprints were allegedly all over even that decision! While the public and even the Queen were said to be very much in favor of the coupling, Charles was less convinced.
He chose to confide his concerns in two women – Camilla and Lady Dale Tryon (pictured here) – both of whom were married at the time. According to a 1985 Vanity Fair article, the two signed off on the “blushing little Spencer girl,” figuring she wouldn’t give them any trouble. Taking his confidantes’ advice to heart, Charles caved, and proposed.
Proposing in Camilla’s back garden
There seem to exist varying accounts on how Charles actually popped the question to his new flame. While some royal experts have placed the proposal at Windsor Castle’s nursery, others claimed it came over dinner in Charles’ Buckingham Palace apartments.
Perhaps most intriguing, though, is a third option, floated by royal biographer Anthony Holden. Writing in 1993, Holden claimed that Charles proposed to Diana… in the cabbage patch located in the Parker Bowleses’ back garden! While we don’t know if that was indeed the case, it’s a troubling scenario.
Nothing in place to protect her
Even though she had been front and center in the public eye even since she began dating Charles, once Diana said “yes” to his proposal things reached a fever pitch. Royal author Penny Junor explained just how intimidating that was for someone as unprepared as Diana.
The soon-to-be-princess, she added, found the pressure unbearable. Diana herself proved it, when she spoke later about how much she remained cooped at home, crying. “I just couldn’t cope with it,” she admitted. And since Diana was merely a girlfriend at the time, there was no mechanism in place to protect her.
Princess Grace’s chilling words to Diana
Things weren’t any easier for Diana as Charles’ fiancee either. Her first public engagement came in March, 1982, a month after Charles proposed. It was a gala at London’s Royal Opera House, and former Hollywood starlet and current Princess of Monaco Grace Kelly was also in attendance. Diana wore a black ballgown with a plunging neckline, which some thought was a little too revealing, and she was terrified.
Biographer Andrew Morton recalled that Princess Grace, well-versed in celebrity life as she was, immediately picked up on Diana’s discomfort. She took her aside, and said, “Don’t worry. It’ll get worse.” She was joking, of course, but the tragedy was that she ended up being right – about both of them…
Married the wrong prince?
Considering Charles and Camilla seemed to be a match made in heaven, it’s interesting to not Diana might have actually fared better if she’d gotten involved with a different royal altogether – Charles’ younger brother, and a spare himself, Prince Andrew!
The two were said to have been close, and Diana even reportedly said she would marry him when she was a girl. Some palace sources even said they seemed more compatible with each other than Diana and Charles did. Alas, it was not to be.
The mystery of Harry’s real father
While she may have missed out on Prince Andrew, who ended up marrying Sarah Ferguson, Diana supposedly gave Charles a run for his money in the infidelity department. In fact, Harry’s fiery red hair, which Charles remarked on when he first saw him, may have been the result of one such indiscretion.
Diana had had an affair with Army Captain James Hewitt, who taught her and her two boys horseback riding in the late 1980s – and also happened to have ginger hair. However, we can debunk that theory – Diana and Hewitt didn’t meet until two years after Harry’s birth.
Diana’s secret letters
He might not have been Harry’s father, but Hewitt’s illicit liaison with the Princess of Wales definitely illuminated how starved she had been for affection – from Charles, but also from the rest of the Royal Family.
Her secret love letters to Hewitt, included in Morton’s book, revealed how furious she was at the feelings Charles continued to harbor for Camilla. However, she seemed to be no less wounded and hurt by the fact that Queen Elizabeth seemed to like her arch-nemesis too.
A premature end
Diana’s pregnancy with Harry wasn’t actually her second – it was allegedly her third! In September, 1983, when William was just over a year old, the entire U.K. was abuzz with speculation as to whether Diana was pregnant again. British tabloids ran competing headlines, with some claiming the Princess of Wales was expecting and others denying it up and down London.
In the same month, Diana only furthered speculation when she cut a Royal Family vacation in the Balmoral estate in Scotland short by returning to London. That same day, royal gynecologist George Pinker also returned from vacation. Coincidence? The truth only came out much later – Diana had allegedly suffered a miscarriage. Heartbreakingly, she had no choice but to try again.
Finally getting that girl
As for Charles, it seemed he never gave up on his desire for female offspring. While he never had any more children with Diana, and by the time he married Camilla in 2005 it was too late for him to have any children with her, in 2015 he finally got his wish.
After Prince George was born in 2013, Prince William and Kate Middleton produced a spare of their own – Princess Charlotte. Charles was beside himself with joy. “I was hoping for a granddaughter,” he candidly told reporters, “someone to look after me when I am very old.”
How different it is now
Looking at Charles and Diana’s two boys, Princes William and Harry, it seems like the heartaches and heartbreaks of the past are just that – in the past. Their loving relationships, and marriages, to Kate Middleton and Meghan Markle seem to prove that the two royals, who grew up in the shadow of their own parents’ imploding marriage, are determined to go about things differently.
It certainly seems like they’ve succeeded so far, William having been married since 2011 and now having three children, and Harry having been married since 2018 with one child.
Repeating the mistakes of the past?
“History doesn’t repeat itself,” Mark Twain supposedly said, “but it rhymes.” For the past eight years, it seemed like William and Kate really did have a fairytale marriage. It’s recently been reported, however, that just as it was with Diana, things might not be what they appear.
In 2019, British press alleged William might’ve been having an affair of his own, and with one of Kate’s friends no less. Former model Rose Hanbury, the supposed “other woman,” has reportedly been ostracized on Kate’s orders. We can only hope it’s nothing more than tabloid gossip. If nothing else, Diana demonstrated how quickly that could spiral out of control.
Charles offended Diana with a joke – again
As if the joke about Harry wasn’t bad enough, it seems Prince Charles couldn’t stop putting his foot in his mouth when it came to Diana. On two separate occasions, he told the same off-color joke – and Diana wasn’t laughing either time!
Speaking about royal walkabouts, Charles joked – in front of a large gathering, mind you – that he would’ve liked to have had two women to cover both sides of the street, leaving him merely to “direct the operation.” Not exactly a winner for someone whose infidelity was public knowledge, and Diana’s stone-faced expression told the whole story without using any words.
Echoing the joke
Of course, Princess Diana ended up being the royal who got the last laugh. In an explosive 1995 interview with Martin Bashir that rocked the monarchy to its very core, Diana spoke with unprecedented honesty about life in the Royal Family – and her personal struggles.
Bashir asked her point-blank whether she thought Camilla contributed to the breakdown of her marriage, and she replied with bitter humor, “Well, there were three of us in this marriage, so it was a bit crowded.” The Queen was furious – but it was worth it.
Both wanted out before it even began?
In all actuality, Princess Diana’s union with Charles may have been doomed before it began, as both had serious reservations about going through with the marriage. In the month before their wedding, Charles reportedly confided in a friend that he didn’t yet love his future wife, but he was “sure he could.”
As for Diana, she reportedly told her sisters on the afternoon before the wedding that she couldn’t go through with it. Her sisters then allegedly told her that her face was already on the tea towels, so she might as well. Ever dutiful, she did.
The mother-in-law that might have been
Diana is no longer with us, sadly, but it wasn’t just us who were robbed of her presence – it was also newer royals who never got to know her. Both Kate Middleton and Meghan Markle were robbed of a mother-in-law.
As far as Meghan goes, former royal protection officer and Diana confidant Ken Wharfe shed some light. Diana, he claimed, would’ve loved Meghan and the breath of fresh air she brought to the Royal Family. ‘This is fantastic,’ he envisioned Diana saying, ‘this is the future of this family, this is the way it has to be.’
Like father, like sons
Of course, if William and Harry have something of a naughty streak, Prince Charles only has himself to blame. What goes around comes around, they say, and Charles got to experience that firsthand as his boys played a practical joke on him.
Diana’s former personal trainer Carolan Brown revealed that the Princess once took the boys to a joke shop when they were young, and they bought stink bombs. They then proceeded to set them off in Charles’ office, causing him to go “absolutely mad.” As for Diana, she just laughed.
That awkward interview
Although Charles and Diana’s split was devastating, we definitely should have seen it coming a mile off. After the two got engaged, they gave an interview during which the Prince made it clear that he wasn’t head over heels for his fiancee.
When asked if he was in love, he responded with “Whatever ‘in love’ means.” It was a stark contrast to Diana’s declaration of “Of course,” and it proved that the pair weren’t on the same wavelength. Unfortunately, things only got worse for the two of them from there.
It seems that Charles doesn’t have the best reputation when it comes to interviews. In 1994, several years after he and Diana had parted ways, the Prince spoke to Jonathan Dimbleby about his marriage. He did this in an effort to improve his reputation, but his choice of words only made things worse.
He told the interviewer that he had been faithful and honorable to his wife until their marriage “became irretrievably broken down.” This admission of infidelity did not go down well with the public or the Royal Family.
The revenge dress
That day in 1994, when Charles’ interview aired, has been cemented in history for several reasons. Not only did the Prince share that he’d been unfaithful, but his wife also stepped out in what’s now been dubbed as ‘the revenge dress.’
The outfit attracted attention for going against royal protocol, and many saw it as Diana finally breaking free from the monarchy. It scored her many points with fans, whereas Charles’ interview simply lost him even more support from the public. It was a terrible time to be the Prince.
Leaked by the press
Charles’ admission came a year after the press leaked an embarrassing telephone conversation that the Prince had with Camilla. In the recording, he told the woman how he wanted to “live inside her trousers,” something incredibly unbefitting of a royal.
It brought further disgrace to the man who’d only recently announced his separation from Diana. Considering all the drama around this phone call, it’s amazing that Charles still has a positive relationship with the public. Of course, it’s taken years for the man to rebuild everything that the scandal destroyed.
Hindsight is 20/20
In many ways, it probably would have been better for everyone involved if Charles and Camilla had gotten married when they had the chance. It would have saved Diana plenty of heartbreak, and it may have even prevented her tragic end in 1997.
Of course, the marriage between Charles and Camilla would have never gotten approval back then, because some royals allegedly considered the woman an unsuitable bride. Obviously, they changed their tune after all the drama with the love triangle, though, because the two tied the knot in 2005.