King Edward VIII and Wallis Simpson

Heritage Images/Getty Images

We’re starting with an oldie but a goodie. Did you know that Queen Elizabeth II never expected to be queen when she was a young royal? Yep! Her uncle, King Edward VIII (her father’s eldest brother), was the direct heir to the British throne and took the crown in 1936 — with a great amount of hesitation. As it happened, Edward was in love with a “two-time divorcee” — and American to boot — Wallis Simpson, but the confines of his role did not permit the two to marry. Determined to spend his life with Simpson, Edward — very controversially — abdicated the throne the same year that he took it, causing a tailspin of royal drama and the eventual crowning of King George VI (Elizabeth’s father). Not only did this coupling completely throw the monarchy off its prescribed path, but it clearly displayed to the British people that Edward’s own desires would come first.

As noted by Brides, Edward was prepared to give up the throne for the love of his life, telling the prime minister and his mother, Queen Mary, of his intentions. His family unsurprisingly told him that pursuing such a relationship and marriage was a fruitless venture, but Edward maintained that he could not stay on the throne without Wallis in his life. The couple got married in 1937, tying the knot in a very intimate ceremony. None of the royal family members, however, were in attendance. The course of the modern monarchy was forever changed by Edward’s singular decision.

Prince Harry and Meghan Markle

WPA Pool/Getty Images

Of course, we couldn’t have a controversial royal wedding list without including Prince Harry and Meghan Markle, the Duke and Duchess of Sussex. While some are firmly on team Meghan and Harry and others find themselves gravitating to the side of the royal family, the couple’s actual wedding was picture perfect. But of course, it wasn’t without drama.

Let’s start way back at the beginning — when Harry introduced Meghan to the royal scene. Meghan’s identity as a mixed-race American divorcee sadly and unfairly led to some adverse reactions. The media frenzy and backlash — which was mostly rooted in blatant racism — was immense and all-encompassing. The Daily Mail’s headline, “Harry’s new girl is (almost) straight outta Compton,” is just one example of the racist undertones Meghan was met with when trying to tie the knot with Harry. As far as the actual wedding itself, a ton of drama and controversy surrounded Meghan’s extended family members and their involvement on the day. Her father, Thomas Markle, famously fumbled the wedding plans as he staged paparazzi photos: The pictures depicted him trying on a suit, reading a travel book about Great Britain, as well as other “hammy” displays. Thomas ultimately claimed that he would not attend the wedding due to a then-recent heart attack, The Washington Post notes, but the public damage to the couple was already done.

Prince Rainier and Grace Kelly

Print Collector/Getty Images

We’re going back to the golden age of Hollywood for this dramatic royal wedding and couple controversy. At the height of her success, actress Grace Kelly was synonymous with style, grace, and that old Hollywood glam — the only way she could top her reputation was by becoming a princess, so that’s what she did. As noted by the Independent, Kelly packed 80 suitcases — literally — and started her life as a royal in 1956 after marrying Monaco’s Prince Rainier III. Having met the prince while filming “To Catch A Thief” in the French Riviera, Kelly admitted that her previous relationships hadn’t been fruitful — maybe a prince would change all that.

“I had been through several unhappy romances,” Kelly said of her romantic life. “Although I had become a star, I was feeling lost and confused. I didn’t want to drift into my 30s without knowing where I was going in my personal life.” While the wedding should’ve marked the start of a new chapter for Kelly, celebrity biographer Wendy Leigh attested that life in Monaco — and with the prince — was not at all what the actress had envisioned. Rainier, it’s said, had “taken at least three mistresses” in the months that followed the wedding, leaving Kelly “humiliated,” according to Leigh, who continued, “[Kelly] was extremely unhappy. She was surrounded by decadence and Rainier’s disreputable friends.” Kelly tragically died at the age of 52 after sustaining a car crash, the conspiracy of which is still alive to this day.

King Henry VIII and Anne Boleyn

Print Collector/Getty Images

This is the controversial royal wedding that started the controversial royal wedding trend, and we’re talking about none other than King Henry VIII and Anne Boleyn. For this story, we have to go all the way back to 1509, so strap in. As noted by Insider, King Henry VIII was happily doing his thing as monarch, and observing Catholicism while doing so. He was already married to Catherine of Aragon, and from what we can tell, everything was going as smoothly as life in the 1500s allowed. But, as luck would have it, Henry fell for his mistress, Anne, and decided that he wanted to divorce Catherine and marry Anne instead. But — as anyone familiar with Catholicism can tell you — divorce is not allowed within the religion, but Henry was set on marrying Anne. So what did he do? He started his own religion, because kings can do that, apparently. Thus, the Church of England was born, and Henry married Anne.

Royal Central further notes that this entire episode — wanting to divorce Catherine, creating the Church of England, marrying Anne — spanned over a five year period of “religious revolution and … international controversy.” And, of course, the drama between Henry and Anne wasn’t over. Insider further notes that, suspicious of Anne’s fidelity to him, Henry had her beheaded in classic medieval fashion. He was married another four times throughout his life — so clearly, creating the Church of England worked in King Henry VIIIs’s favor.

Queen Beatrix and Prince Claus

Express/Getty Images

If racism, divorce, and beheading wasn’t enough, we have another problematic layer to add to the list of controversial weddings — this time, we’re taking a closer look at the Netherlands’ Queen Beatrix and her marriage to Prince Claus. As noted by The Court Jeweller, Beatrix and Claus met at a dinner party in 1964, and later crossed paths at a — you guessed it — royal wedding. A ski trip followed, as did a blooming romance between the two. Sounds innocent, right? Wrong.

As it turns out, Claus had been a member of the Hitler Youth and was a soldier for Germany during World War II. Given that it was the 1960s and the memories of the war were still fresh for many Europeans, Beatrix and Claus’s romance was met with vitriol as soon as it began. As a result, the couple was forced to address Claus’s history. Claiming that he “did not like” the Hitler Youth and his involvement was compulsory, Claus retorted at the time “that he did not think it right to condemn a man simply because he had worn the German uniform.” This, naturally, left a bad taste for many, and the Dutch people were adamant that their future queen not marry a former member of the German army. Despite the controversy, Beatrix and Claus got married in Amsterdam, and up to 100,000 people lined the streets to watch the nuptials unfold.

King Charles III and Diana Spencer

Anwar Hussein/Getty Images

Oh boy, where do we even start with this one? The wedding between then-Prince Charles and Diana Spencer was seen by thousands as a fairytale, but the reality was far more akin to a nightmare. Before the wedding bells were ringing, the distance between Charles and Diana was incredibly apparent, with Charles famously answering the question, “Are you in love?” with, “Whatever ‘in love’ means” (via Harper’s Bazaar). Cue the disaster signals.

Of course, Charles was 32 years old to Diana’s 19 when they got engaged, and he was still very much involved in Camilla Parker Bowles’s life at the time, even gifting her meaningful jewelry in the lead up to his wedding to Diana. Just before the big day itself, Diana was said to have many hesitations and doubts about the wedding, telling a friend that she desperately wanted to call it off. “One of the most shocking things that Diana told me was that the night before the wedding Charles told her that he didn’t love her,” Penny Thornton said during ITV’s documentary, “The Diana Interview: Revenge of a Princess.” “I think Charles didn’t want to go into the wedding on a false premise. He wanted to square it with her and it was devastating for Diana.” Of course, the two did get married, but their union was famously not a happy one. They formally divorced in 1996, and Diana tragically died in 1997.

Princess Margaret and Lord Snowdon

Print Collector/Getty Images

Anyone who’s watched “The Crown” Seasons 1 and 2 knows that Princess Margaret’s romantic life was anything but easy. Falling in love with Peter Townsend as a young woman, Queen Elizabeth II’s sister found herself at an incredibly difficult crossroads — she could not marry the then-divorced Townsend due to her status as a royal, and she ultimately put the crown above her own happiness. Margaret went on to marry Antony Armstrong-Jones — known as Lord Snowdon — and yet her second attempt at love was not entirely fruitful either.

As noted by People, Margaret and Armstrong-Jones met at a party in the late 1950s, and kept the truth about their romantic relationship under wraps practically up until their February 1960 engagement. Just three months later, they got married, but the whirlwind surrounding their wedding and early marriage was not cloaked in positivity. “During the 60s, before their marriage started going wrong, they were royalty’s golden couple,” Christoper Warwick, Princess Margaret’s biographer, told People. “Stories about them were legion, with their star-studded parties at Kensington Palace. If you were being invited by them you were being invited to breathe in rarified air.” But, like many royal couples who would follow them, Margaret and Armstrong-Jones pulled the plug on their marriage, bringing an element of shame to the royals and the crown’s image as a whole. “She did tarnish the family’s reputation but she cleared the way for others to get out of unhappy marriages,” Jennie Bond said in the Channel 5 documentary, “Princess Margaret: A Rebel Without a Crown.”

King Charles III and Queen Consort Camilla

Pool/Getty Images

We hate to break it to King Charles III, but he’s on this list twice. His 2005 wedding to Camilla Parker Bowles, now Queen Consort Camilla, was a long time coming. He and Camilla had been in each other’s lives — platonically and romantically — since the 1970s, and while many Britons didn’t love the idea of their union, the couple finally tied the knot. Of course, in expected royal flair, the day didn’t come and go without some controversy. First and foremost, Charles and Camilla didn’t have a grand ceremony in Westminster Abbey the likes that we’ve seen for other royal couples. Instead, they had a civil ceremony at Windsor and a blessing from the Archbishop of Canterbury at St. George’s Chapel, per Good Housekeeping. Furthermore, Queen Elizabeth II made it clear that she would not be attending the second wedding of her eldest son, insisting that her role as the head of the Church of England had to come first. Of course, it wasn’t the best look for the day, especially given Camilla’s sordid history with the royal family.

To make matters worse, the public was firmly against Charles and Camilla’s union. Penny Junor shared in “The Firm: The Troubled Life of the House of Windsor” that she received emails from Britons ahead of the wedding, expressing their disgust at the union. To this day, YouGov polling doesn’t have Camilla and Charles reigning the top of the public approval list.

Prince Albert and Princess Charlene of Monaco

Dan Kitwood/Getty Images

Last, but certainly not least: We have to include the wedding of Prince Albert and Princess Charlene of Monaco, as their seemingly “happy” day and the lead up to it was fraught with controversy. As noted by Now To Love, many had their suspicions about the royal couple before they tied the knot thanks to their two-decade age gap, but that was far down the list of troubles they faced. As it turns out, Albert had a child — who was the result of a love affair — who was conceived while he was said to be dedicated to Charlene. Albert already had two children as the results of affairs prior, so while the news wasn’t entirely unexpected, it likely shook the bride off her feet.

Then came the day in question. As noted by Hello! Magazine, Charlene was seen wiping tears from her face during the ceremony, and to say that she looked a bit displeased is an understatement. Yet, she shut down any naysayers by expressing that her tears were the result of being overwhelmed. “Everything was just so overwhelming and there were all the mixed emotions because of the rumors, and obviously the tension built up and I burst into tears [immediately after the ceremony],” Charlene said of the day. “And then I burst into tears some more because I was thinking ‘Oh no, now the whole world has seen me cry.’”

Royal Weddings That Sparked A Lot Of Controversy

Anwar Hussein/Getty Images

We may receive a commission on purchases made from links. Correction 11/3/22: An earlier version of this article misidentified Meghan Markle as the first American divorcee to marry into the royal family. This reference has been removed. While the royals of the world are known for lavish lifestyles, dazzling crowns, and oh so much drama, there are some members of international royalty that bring the drama more than others. Take the newly named King Charles III, for instance — a bachelor well into his 30s and the then-direct heir to the throne, Charles’s long-standing affair with Camilla Parker Bowles ruined many a relationship he tried to sustain, ultimately leading the royal down the path of divorce alongside the still-beloved Diana Spencer. Even his eldest son, Prince William of Wales — who is known for his level-headedness and approach to the crown — has been involved with drama, as rumors of infidelity have plagued him and wife of a decade-plus, Catherine, Princess of Wales. It seems as though no one is safe from controversy if tied to the crown of a given country — and the spotlight certainly doesn’t help.

Now when we ponder royal events in all their lavish glory, royal weddings certainly stand out. Often referred to as events of the decade in question, weddings among the royals are known for being grand, celebratory affairs — simply put, no expense is too much, no specification is too overbearing, and everything has to be just right. While the wedding days themselves often go without a hitch, sometimes it’s the actual couple getting married that has people seeing red. So, without further ado, these are the royal weddings (and royal couples, at that) that have sparked a lot of controversy.

We may receive a commission on purchases made from links.

While the royals of the world are known for lavish lifestyles, dazzling crowns, and oh so much drama, there are some members of international royalty that bring the drama more than others. Take the newly named King Charles III, for instance — a bachelor well into his 30s and the then-direct heir to the throne, Charles’s long-standing affair with Camilla Parker Bowles ruined many a relationship he tried to sustain, ultimately leading the royal down the path of divorce alongside the still-beloved Diana Spencer. Even his eldest son, Prince William of Wales — who is known for his level-headedness and approach to the crown — has been involved with drama, as rumors of infidelity have plagued him and wife of a decade-plus, Catherine, Princess of Wales. It seems as though no one is safe from controversy if tied to the crown of a given country — and the spotlight certainly doesn’t help.

Now when we ponder royal events in all their lavish glory, royal weddings certainly stand out. Often referred to as events of the decade in question, weddings among the royals are known for being grand, celebratory affairs — simply put, no expense is too much, no specification is too overbearing, and everything has to be just right. While the wedding days themselves often go without a hitch, sometimes it’s the actual couple getting married that has people seeing red. So, without further ado, these are the royal weddings (and royal couples, at that) that have sparked a lot of controversy.

King Edward VIII and Wallis Simpson

Heritage Images/Getty Images

We’re starting with an oldie but a goodie. Did you know that Queen Elizabeth II never expected to be queen when she was a young royal? Yep! Her uncle, King Edward VIII (her father’s eldest brother), was the direct heir to the British throne and took the crown in 1936 — with a great amount of hesitation. As it happened, Edward was in love with a “two-time divorcee” — and American to boot — Wallis Simpson, but the confines of his role did not permit the two to marry. Determined to spend his life with Simpson, Edward — very controversially — abdicated the throne the same year that he took it, causing a tailspin of royal drama and the eventual crowning of King George VI (Elizabeth’s father). Not only did this coupling completely throw the monarchy off its prescribed path, but it clearly displayed to the British people that Edward’s own desires would come first.

As noted by Brides, Edward was prepared to give up the throne for the love of his life, telling the prime minister and his mother, Queen Mary, of his intentions. His family unsurprisingly told him that pursuing such a relationship and marriage was a fruitless venture, but Edward maintained that he could not stay on the throne without Wallis in his life. The couple got married in 1937, tying the knot in a very intimate ceremony. None of the royal family members, however, were in attendance. The course of the modern monarchy was forever changed by Edward’s singular decision.

As noted by Brides, Edward was prepared to give up the throne for the love of his life, telling the prime minister and his mother, Queen Mary, of his intentions. His family unsurprisingly told him that pursuing such a relationship and marriage was a fruitless venture, but Edward maintained that he could not stay on the throne without Wallis in his life. The couple got married in 1937, tying the knot in a very intimate ceremony. None of the royal family members, however, were in attendance. The course of the modern monarchy was forever changed by Edward’s singular decision.

Prince Harry and Meghan Markle

WPA Pool/Getty Images

Of course, we couldn’t have a controversial royal wedding list without including Prince Harry and Meghan Markle, the Duke and Duchess of Sussex. While some are firmly on team Meghan and Harry and others find themselves gravitating to the side of the royal family, the couple’s actual wedding was picture perfect. But of course, it wasn’t without drama.

Let’s start way back at the beginning — when Harry introduced Meghan to the royal scene. Meghan’s identity as a mixed-race American divorcee sadly and unfairly led to some adverse reactions. The media frenzy and backlash — which was mostly rooted in blatant racism — was immense and all-encompassing. The Daily Mail’s headline, “Harry’s new girl is (almost) straight outta Compton,” is just one example of the racist undertones Meghan was met with when trying to tie the knot with Harry. As far as the actual wedding itself, a ton of drama and controversy surrounded Meghan’s extended family members and their involvement on the day. Her father, Thomas Markle, famously fumbled the wedding plans as he staged paparazzi photos: The pictures depicted him trying on a suit, reading a travel book about Great Britain, as well as other “hammy” displays. Thomas ultimately claimed that he would not attend the wedding due to a then-recent heart attack, The Washington Post notes, but the public damage to the couple was already done.

Let’s start way back at the beginning — when Harry introduced Meghan to the royal scene. Meghan’s identity as a mixed-race American divorcee sadly and unfairly led to some adverse reactions. The media frenzy and backlash — which was mostly rooted in blatant racism — was immense and all-encompassing. The Daily Mail’s headline, “Harry’s new girl is (almost) straight outta Compton,” is just one example of the racist undertones Meghan was met with when trying to tie the knot with Harry.

As far as the actual wedding itself, a ton of drama and controversy surrounded Meghan’s extended family members and their involvement on the day. Her father, Thomas Markle, famously fumbled the wedding plans as he staged paparazzi photos: The pictures depicted him trying on a suit, reading a travel book about Great Britain, as well as other “hammy” displays. Thomas ultimately claimed that he would not attend the wedding due to a then-recent heart attack, The Washington Post notes, but the public damage to the couple was already done.

Princess Mako of Japan and Kei Komuro

Pool/Getty Images

“I love Mako. I would like to spend my one life with the person I love,” Komuro said during a press conference about the wedding, walking a path with the princess that The New York Times described as “torturous.” The couple’s journey certainly was not easy — Mako’s father bit his tongue about her and Komuro, refusing to comment publicly and allowing discourse among the Japanese people to implode. Komuro was even chased by paparazzi while attending law school in New York, and the vitriol on social media resulted in a post-traumatic stress disorder diagnosis for Mako.

Prince Rainier and Grace Kelly

Print Collector/Getty Images

We’re going back to the golden age of Hollywood for this dramatic royal wedding and couple controversy. At the height of her success, actress Grace Kelly was synonymous with style, grace, and that old Hollywood glam — the only way she could top her reputation was by becoming a princess, so that’s what she did. As noted by the Independent, Kelly packed 80 suitcases — literally — and started her life as a royal in 1956 after marrying Monaco’s Prince Rainier III. Having met the prince while filming “To Catch A Thief” in the French Riviera, Kelly admitted that her previous relationships hadn’t been fruitful — maybe a prince would change all that.

“I had been through several unhappy romances,” Kelly said of her romantic life. “Although I had become a star, I was feeling lost and confused. I didn’t want to drift into my 30s without knowing where I was going in my personal life.” While the wedding should’ve marked the start of a new chapter for Kelly, celebrity biographer Wendy Leigh attested that life in Monaco — and with the prince — was not at all what the actress had envisioned. Rainier, it’s said, had “taken at least three mistresses” in the months that followed the wedding, leaving Kelly “humiliated,” according to Leigh, who continued, “[Kelly] was extremely unhappy. She was surrounded by decadence and Rainier’s disreputable friends.” Kelly tragically died at the age of 52 after sustaining a car crash, the conspiracy of which is still alive to this day.

“I had been through several unhappy romances,” Kelly said of her romantic life. “Although I had become a star, I was feeling lost and confused. I didn’t want to drift into my 30s without knowing where I was going in my personal life.”

While the wedding should’ve marked the start of a new chapter for Kelly, celebrity biographer Wendy Leigh attested that life in Monaco — and with the prince — was not at all what the actress had envisioned. Rainier, it’s said, had “taken at least three mistresses” in the months that followed the wedding, leaving Kelly “humiliated,” according to Leigh, who continued, “[Kelly] was extremely unhappy. She was surrounded by decadence and Rainier’s disreputable friends.” Kelly tragically died at the age of 52 after sustaining a car crash, the conspiracy of which is still alive to this day.

King Henry VIII and Anne Boleyn

This is the controversial royal wedding that started the controversial royal wedding trend, and we’re talking about none other than King Henry VIII and Anne Boleyn. For this story, we have to go all the way back to 1509, so strap in. As noted by Insider, King Henry VIII was happily doing his thing as monarch, and observing Catholicism while doing so. He was already married to Catherine of Aragon, and from what we can tell, everything was going as smoothly as life in the 1500s allowed. But, as luck would have it, Henry fell for his mistress, Anne, and decided that he wanted to divorce Catherine and marry Anne instead. But — as anyone familiar with Catholicism can tell you — divorce is not allowed within the religion, but Henry was set on marrying Anne. So what did he do? He started his own religion, because kings can do that, apparently. Thus, the Church of England was born, and Henry married Anne.

Royal Central further notes that this entire episode — wanting to divorce Catherine, creating the Church of England, marrying Anne — spanned over a five year period of “religious revolution and … international controversy.” And, of course, the drama between Henry and Anne wasn’t over. Insider further notes that, suspicious of Anne’s fidelity to him, Henry had her beheaded in classic medieval fashion. He was married another four times throughout his life — so clearly, creating the Church of England worked in King Henry VIIIs’s favor.

Royal Central further notes that this entire episode — wanting to divorce Catherine, creating the Church of England, marrying Anne — spanned over a five year period of “religious revolution and … international controversy.” And, of course, the drama between Henry and Anne wasn’t over. Insider further notes that, suspicious of Anne’s fidelity to him, Henry had her beheaded in classic medieval fashion. He was married another four times throughout his life — so clearly, creating the Church of England worked in King Henry VIIIs’s favor.

Queen Beatrix and Prince Claus

Express/Getty Images

If racism, divorce, and beheading wasn’t enough, we have another problematic layer to add to the list of controversial weddings — this time, we’re taking a closer look at the Netherlands’ Queen Beatrix and her marriage to Prince Claus. As noted by The Court Jeweller, Beatrix and Claus met at a dinner party in 1964, and later crossed paths at a — you guessed it — royal wedding. A ski trip followed, as did a blooming romance between the two. Sounds innocent, right? Wrong.

As it turns out, Claus had been a member of the Hitler Youth and was a soldier for Germany during World War II. Given that it was the 1960s and the memories of the war were still fresh for many Europeans, Beatrix and Claus’s romance was met with vitriol as soon as it began. As a result, the couple was forced to address Claus’s history. Claiming that he “did not like” the Hitler Youth and his involvement was compulsory, Claus retorted at the time “that he did not think it right to condemn a man simply because he had worn the German uniform.” This, naturally, left a bad taste for many, and the Dutch people were adamant that their future queen not marry a former member of the German army. Despite the controversy, Beatrix and Claus got married in Amsterdam, and up to 100,000 people lined the streets to watch the nuptials unfold.

As it turns out, Claus had been a member of the Hitler Youth and was a soldier for Germany during World War II. Given that it was the 1960s and the memories of the war were still fresh for many Europeans, Beatrix and Claus’s romance was met with vitriol as soon as it began. As a result, the couple was forced to address Claus’s history. Claiming that he “did not like” the Hitler Youth and his involvement was compulsory, Claus retorted at the time “that he did not think it right to condemn a man simply because he had worn the German uniform.” This, naturally, left a bad taste for many, and the Dutch people were adamant that their future queen not marry a former member of the German army.

Despite the controversy, Beatrix and Claus got married in Amsterdam, and up to 100,000 people lined the streets to watch the nuptials unfold.

King Charles III and Diana Spencer

Oh boy, where do we even start with this one? The wedding between then-Prince Charles and Diana Spencer was seen by thousands as a fairytale, but the reality was far more akin to a nightmare. Before the wedding bells were ringing, the distance between Charles and Diana was incredibly apparent, with Charles famously answering the question, “Are you in love?” with, “Whatever ‘in love’ means” (via Harper’s Bazaar). Cue the disaster signals.

Of course, Charles was 32 years old to Diana’s 19 when they got engaged, and he was still very much involved in Camilla Parker Bowles’s life at the time, even gifting her meaningful jewelry in the lead up to his wedding to Diana. Just before the big day itself, Diana was said to have many hesitations and doubts about the wedding, telling a friend that she desperately wanted to call it off. “One of the most shocking things that Diana told me was that the night before the wedding Charles told her that he didn’t love her,” Penny Thornton said during ITV’s documentary, “The Diana Interview: Revenge of a Princess.” “I think Charles didn’t want to go into the wedding on a false premise. He wanted to square it with her and it was devastating for Diana.” Of course, the two did get married, but their union was famously not a happy one. They formally divorced in 1996, and Diana tragically died in 1997.

Of course, Charles was 32 years old to Diana’s 19 when they got engaged, and he was still very much involved in Camilla Parker Bowles’s life at the time, even gifting her meaningful jewelry in the lead up to his wedding to Diana. Just before the big day itself, Diana was said to have many hesitations and doubts about the wedding, telling a friend that she desperately wanted to call it off.

“One of the most shocking things that Diana told me was that the night before the wedding Charles told her that he didn’t love her,” Penny Thornton said during ITV’s documentary, “The Diana Interview: Revenge of a Princess.” “I think Charles didn’t want to go into the wedding on a false premise. He wanted to square it with her and it was devastating for Diana.” Of course, the two did get married, but their union was famously not a happy one. They formally divorced in 1996, and Diana tragically died in 1997.

Princess Margaret and Lord Snowdon

Anyone who’s watched “The Crown” Seasons 1 and 2 knows that Princess Margaret’s romantic life was anything but easy. Falling in love with Peter Townsend as a young woman, Queen Elizabeth II’s sister found herself at an incredibly difficult crossroads — she could not marry the then-divorced Townsend due to her status as a royal, and she ultimately put the crown above her own happiness. Margaret went on to marry Antony Armstrong-Jones — known as Lord Snowdon — and yet her second attempt at love was not entirely fruitful either.

As noted by People, Margaret and Armstrong-Jones met at a party in the late 1950s, and kept the truth about their romantic relationship under wraps practically up until their February 1960 engagement. Just three months later, they got married, but the whirlwind surrounding their wedding and early marriage was not cloaked in positivity. “During the 60s, before their marriage started going wrong, they were royalty’s golden couple,” Christoper Warwick, Princess Margaret’s biographer, told People. “Stories about them were legion, with their star-studded parties at Kensington Palace. If you were being invited by them you were being invited to breathe in rarified air.” But, like many royal couples who would follow them, Margaret and Armstrong-Jones pulled the plug on their marriage, bringing an element of shame to the royals and the crown’s image as a whole. “She did tarnish the family’s reputation but she cleared the way for others to get out of unhappy marriages,” Jennie Bond said in the Channel 5 documentary, “Princess Margaret: A Rebel Without a Crown.”

As noted by People, Margaret and Armstrong-Jones met at a party in the late 1950s, and kept the truth about their romantic relationship under wraps practically up until their February 1960 engagement. Just three months later, they got married, but the whirlwind surrounding their wedding and early marriage was not cloaked in positivity.

“During the 60s, before their marriage started going wrong, they were royalty’s golden couple,” Christoper Warwick, Princess Margaret’s biographer, told People. “Stories about them were legion, with their star-studded parties at Kensington Palace. If you were being invited by them you were being invited to breathe in rarified air.”

But, like many royal couples who would follow them, Margaret and Armstrong-Jones pulled the plug on their marriage, bringing an element of shame to the royals and the crown’s image as a whole. “She did tarnish the family’s reputation but she cleared the way for others to get out of unhappy marriages,” Jennie Bond said in the Channel 5 documentary, “Princess Margaret: A Rebel Without a Crown.”

King Charles III and Queen Consort Camilla

We hate to break it to King Charles III, but he’s on this list twice. His 2005 wedding to Camilla Parker Bowles, now Queen Consort Camilla, was a long time coming. He and Camilla had been in each other’s lives — platonically and romantically — since the 1970s, and while many Britons didn’t love the idea of their union, the couple finally tied the knot. Of course, in expected royal flair, the day didn’t come and go without some controversy. First and foremost, Charles and Camilla didn’t have a grand ceremony in Westminster Abbey the likes that we’ve seen for other royal couples. Instead, they had a civil ceremony at Windsor and a blessing from the Archbishop of Canterbury at St. George’s Chapel, per Good Housekeeping. Furthermore, Queen Elizabeth II made it clear that she would not be attending the second wedding of her eldest son, insisting that her role as the head of the Church of England had to come first. Of course, it wasn’t the best look for the day, especially given Camilla’s sordid history with the royal family.

To make matters worse, the public was firmly against Charles and Camilla’s union. Penny Junor shared in “The Firm: The Troubled Life of the House of Windsor” that she received emails from Britons ahead of the wedding, expressing their disgust at the union. To this day, YouGov polling doesn’t have Camilla and Charles reigning the top of the public approval list.

To make matters worse, the public was firmly against Charles and Camilla’s union. Penny Junor shared in “The Firm: The Troubled Life of the House of Windsor” that she received emails from Britons ahead of the wedding, expressing their disgust at the union. To this day, YouGov polling doesn’t have Camilla and Charles reigning the top of the public approval list.

Prince Andrew and Sarah Ferguson

Derek Hudson/Getty Images

So what does this have to do with Andrew’s wedding? Well, just a hop, skip, and a jump later, the prince married Sarah Ferguson, Duchess of York, who was seen as a young girl suitable enough to introduce to the royal way of life. With Diana Spencer playing match-maker, per Vanity Fair, Andrew and Fergie got married in 1986, seemingly putting an end to Andrew’s many scandals. But of course, the wedding — and marriage as a whole — did not go off without a hitch, and the two became estranged in 1992 and were officially divorced in 1996.

Prince Albert and Princess Charlene of Monaco

Dan Kitwood/Getty Images

Last, but certainly not least: We have to include the wedding of Prince Albert and Princess Charlene of Monaco, as their seemingly “happy” day and the lead up to it was fraught with controversy. As noted by Now To Love, many had their suspicions about the royal couple before they tied the knot thanks to their two-decade age gap, but that was far down the list of troubles they faced. As it turns out, Albert had a child — who was the result of a love affair — who was conceived while he was said to be dedicated to Charlene. Albert already had two children as the results of affairs prior, so while the news wasn’t entirely unexpected, it likely shook the bride off her feet.

Then came the day in question. As noted by Hello! Magazine, Charlene was seen wiping tears from her face during the ceremony, and to say that she looked a bit displeased is an understatement. Yet, she shut down any naysayers by expressing that her tears were the result of being overwhelmed. “Everything was just so overwhelming and there were all the mixed emotions because of the rumors, and obviously the tension built up and I burst into tears [immediately after the ceremony],” Charlene said of the day. “And then I burst into tears some more because I was thinking ‘Oh no, now the whole world has seen me cry.’”

Then came the day in question. As noted by Hello! Magazine, Charlene was seen wiping tears from her face during the ceremony, and to say that she looked a bit displeased is an understatement. Yet, she shut down any naysayers by expressing that her tears were the result of being overwhelmed.

“Everything was just so overwhelming and there were all the mixed emotions because of the rumors, and obviously the tension built up and I burst into tears [immediately after the ceremony],” Charlene said of the day. “And then I burst into tears some more because I was thinking ‘Oh no, now the whole world has seen me cry.’”