The Ugliest Breakups In History

March 8, 2023 | Samantha Henman

The Ugliest Breakups In History

Everyone knows breaking up is hard to do—but these historical splits were unimaginably brutal. From horrific secrets tearing once-happy couples apart all the way to warrior exes meeting on the battlefield, these are, by far, the ugliest breakups in history.

1. Henry VIII's First Victim

We'd be remiss to talk about the ugliest breakups in history without mentioning Henry VIII. As we all know, he was a "love 'em and leave 'em"-type of guy—even if "leave 'em" sometimes meant leaving them in pieces. Henry's condemnation of Anne Boleyn certainly led to his most disturbing breakup, but that's territory that we're all pretty aware of.  But what about his first wife, Catherine of Aragon? What happened to her? Well, when it comes to marrying Henry VIII, first is worst.


2. They Got Off To A Rocky Start

Maybe Catherine and Henry were doomed from the beginning. After all, he wasn't the first Tudor she hooked up with. That's right, Catherine was originally married to Henry's older brother, Prince Arthur. But shortly after their honeymoon, the mysterious "sweating sickness" hit them both, and took Arthur's life. Catherine became a widow at 16—and Henry was now heir to the English throne.

It seemed like her future had been ripped away from her...but she wasn't about to give up that easily.

Catherine of Aragon facts The Spanish Princess (2019– ), All3 Media

3. Her Marriage Was Against the Law

Catherine eventually convinced Henry and his family that she deserved another go as their queen—but there was one big problem hanging over them. Because she had already been married to his brother, they had to get special dispensation from the Pope for the union. Even then, the royals only got a reluctant go-ahead...and only after Catherine made an extremely controversial confession.

Henry and Catherine's petition to the Pope hinged on a single claim: Catherine’s assurance that she and Arthur had never consummated their union. Was it true or not? Who knows. What matters is that it worked. And, either way, it came back to haunt her...

Catherine of Aragon facts The Spanish Princess (2019– ), All3 Media

4. She Couldn't Produce An Heir

Things began moving quickly for the couple. Henry became King of England, tied the knot with Catherine, and then they each had lavish coronation ceremonies. However, all this joy was punctuated by a profound tragedy. While five months pregnant, Catherine went into premature labor and gave birth to a stillborn baby girl.  Sadly, this was just the first of many troubled and/or unsuccessful pregnancies. Catherine eventually did give birth to a son, but he only survived 52 days.

The pressure was on—and it wasn't about to let up.

Catherine of Aragon facts Wikimedia Commons

5. He Cheated On Her

To make matters worse, Catherine found she had a viper in her midst—the aforementioned Anne Boleyn. Henry fell for Anne, who told him she wouldn't sleep with him without a ring on her finger. Henry grew desperate to get rid of Catherine, and he came up with a brutally hurtful excuse to kick her to the curb. According to Henry, their union was cosmically cursed, all because he had broken God’s law when he married his brother’s widow. Then, he turned up the heat.

Catherine of Aragon facts The Spanish Princess (2019– ), All3 Media

6. She Started a Revolution

This "Great Matter" dragged on for years as Henry tried to get the Church to let him bed Anne Boleyn under the approving eye of God. Today, everyone knows it ended in revolution, with Henry taking over as Head of Church, annulling his own marriage, and starting the English Reformation. But how did he actually separate from Catherine? Well, not with honor or grace.

In July 1531, he left Catherine on a hunting trip and never came back. In a letter, Catherine complained that he didn’t even wake her up to say goodbye. And then Henry twisted the knife in.

Catherine of Aragon

7. Her King Banished Her

Catherine never saw Henry again after that moment, but the King didn’t waste time with a silly thing called "remorse". Instead, he doubled down. He banished Catherine from his court, forbid her from seeing their daughter Mary, and then installed Boleyn in her old rooms. When she passed on three years later, Henry and Anne donned yellow clothing. It was a gesture that some saw as celebrating Catherine's demise.  Well, karma's a witch—and Anne then miscarried a son on the day of Catherine's funeral.

Between the lack of heirs and his love for Anne, Henry had many reasons to want to dump Catherine. The same can't be said for Julius Caesar—who famously dumped his wife over a simple misunderstanding...

Catherine of Aragon facts The Tudors, Showtime Networks

8. Pompeia Was An Innocent Victim...

Julius Caesar is perhaps the most infamous of all the rulers of ancient Rome. He was a brutal tyrant and dictator whose own men turned on him. Sounds like a real catch, right? After the loss of his first wife, Caesar mourned for a year or two before picking his next bride, a woman named Pompeia. Well, this union was not only unhappy—it also ended in a wild scandal.

Julius Caesar FactsWikimedia Commons

9. ...But She Got All The Blame

One year during the women-only festival of the Bona Dea, a man named Clodius snuck into the celebrations dressed as a woman, apparently hoping to have a romantic rendez-vous with Pompeia. Authorities caught Clodius and charged him with sacrilege, but Caesar basically let it go—instead, turning his fury toward his unwitting wife. As a result of Clodius's transgression, Caesar divorced Pompeia almost on the spot. He infamously told her that: "the wife of Caesar must be above suspicion".

Pompeia got the short end of the stick—something that the subject of our next ugly breakup, Eleanor of Aquitaine, would never let happen. She was way too cunning for that...

Emperor Hadrian factsShutterstock

10. Not Even The King Of France Could Tame Eleanor Of Aquitaine

Eleanor of Aquitaine was as fierce and formidable as they come. She reigned as queen consort in both England and France in her lifetime, a feat never to be repeated again. Well, you don't get that kind of power without stepping on a few people along the way—or without starting early. Eleanor was 15 when she wed the 17-year-old heir to the French throne, Louis.

Just days after the ceremony, the groom's father passed on, making Eleanor and young Louis VII the rulers of France. So, how was the honeymoon, you ask? Well...

Henry II factsGetty Images

11. It Was An Uneven Match

King Louis was besotted with his new bride, especially admiring Eleanor's intelligence, beauty, and strength. Eleanor, on the other hand, wasn’t nearly as enamored with her husband, specifically struggling with his prim and proper ways. She allegedly proclaimed, "I thought I was wed to a king, now I find I am wed to a monk". Looks like these two have first-class tickets to bedroom problems.

Eleanor of Aquitaine FactsWikimedia Commons

12. She Loathed Him

It wasn't just the lack of a spark that made Eleanor come to detest her husband. It was his weak will, his inability to rule effectively, and the many mistakes he made on the throne, including the ones he illegitimately blamed on her. Well, after more than a decade of Louis VII's nonsense, she'd had enough—so she came up with a brutal plan.

Eleanor of Aquitaine FactsThe Devil

13. She Spoke her Mind

How did Eleanor attempt to dump her husband? Well, she said something that would change European history forever. The furious queen spat that she and her husband shouldn't travel together as man and wife because they were related "in the fourth and fifth degrees". In Medieval speak, this was a total shocker.

Technically, royals couldn't wed if they weren't separated by seven generations. Louis and Eleanor, meanwhile, were only separated by four or five. After so many unhappy years with Louis, Eleanor finally had enough: She would try to end their marriage on grounds of consanguinity.

Eleanor of Aquitaine FactsThe Devil

14. The Pope Denied Her

When Louis and Eleanor got to Jerusalem in 1149, they sought an audience with the Pope and asked him to grant them an annulment. On paper, it was because they were too closely related, but in reality, all the royal couples had intertwined family trees. In actuality, Louis and Eleanor had been married for 15 long years and they still didn't have a male heir. Plus, on a more basic level, Eleanor simply didn't love Louis anymore.

To her devastation, the Pope refused to annul the marriage. Soon, all of Europe was buzzing with the couple's scandalous attempt to split.

Eleanor of Aquitaine FactsThe Devil

15. She Gave It The Old College Try

Eleanor's plot had failed—and so, for a moment, she took the advice of the pope and tried to make things work with Louis VII. Nine months later, the royal couple had a newborn daughter. The king was disappointed; after all, he needed a male heir. But Eleanor was already hatching a diabolical plan to get out of her miserable marriage.

Eleanor of Aquitaine FactsThe Devil

16. She Was A Master Manipulator

Eleanor knew that if she'd given birth to a boy, she'd never be able to dump Louis, so having little baby Alice was a blessing in disguise. The queen used this "failure" to her advantage, continuing to treat Louis coldly and making it clear that their marriage would only bring them both misery. Over time, her ice queen routine took effect. After years of resisting an annulment, Louis and the Pope suddenly changed their mind and granted one to the royal couple.

Louis VIIWikimedia Commons

17. She Had To Abandon Her Children

Louis was heartbroken, but Eleanor was delighted. She was finally free. But, there was one enormous catch to her split, and it weighed heavily on Eleanor's heart. Once she abandoned Louis, she also had to give up all claims to her daughters, including little Alice who wasn't even two years old at the time. Well, the best revenge is living well, and that's exactly what Eleanor did. She used her land titles to offer herself up to the future King of England, Henry II.

It was a smack in the face to Louis—and he knew he had to strike back.

Eleanor of Aquitaine FactsThe Devil

18. Her Ex Was Furious at Her

Most of Louis' anger might have come from jealousy, but he had one legitimate reason to be upset with Eleanor. She'd left him by claiming they were too closely related, then gone and married Henry II...who was an even closer relative! The angry French king did what any bitter royal would do: Start a full-on armed conflict his ex and her new boy toy. Going into battle didn’t work out so well for Louis, who had an awful track record with that kind of thing. He suffered an embarrassing defeat at Henry’s capable hands.

That's taking "adding insult to injury" to the next level. What lesson can be learned here? Don't mess with Eleanor. She was a heartbreaker, for sure—just like Empress Josephine.

Getty Images-51245073 louis VIIGetty Images

19. Empress Josephine Broke Napoleon's Heart

Josephine and Napoleon were the Demi Moore/Ashton Kutcher of their day. Not only was she six years older than her boy toy, but Josephine also had the added scandal of being a widow with two children. Instead of taking a young inexperienced woman to be his bride, Napoleon chose a gal who knew her way around the bedroom. The Bonaparte family was appalled by the marriage, which occurred on March 9, 1796.

Empress Josephine FactsWikimedia Commons

20. Napoleon Was Obsessed With Her

Napoleon absolutely adored Josephine, but unfortunately for him, she wasn't quite as smitten. While he would write his wife elaborate love letters about the "intoxicating pleasures" she gave him, Josephine was known to rarely even read Napoleon's missives. When he cooed over a portrait of his bride and constantly kept it safe in his pocket, apparently Josephine never bothered to look at paintings of her husband.

Empress Josephine FactsNapoleon,France 2

21. She Had A Passionate Affair

Josephine's marriages didn't give her the passionate love affair she desired, so shortly after her second marriage, when Napoleon and his men marched to Italy, she began to look for a new lover. It didn't take long for her to ensnare a brave, good-looking lieutenant named Hippolyte Charles. Their fiery passion would burn for years...until it all unraveled in a spectacular mess.

Eventually, Napoleon confirmed that his bride was being intimate with another man and became furious. In a rage, he officially denounced the two lovers and his love for Josephine. Not only that, he took a mistress or two of his own. Now that's not how you reconcile...

Empress Josephine FactsNapoleon,France 2

22. She Was Pushed Out

Josephine even found Napoleon in her bed with another woman on the day of their coronation. Even after that brutal hit, Napoleon had even more wickedness in store for his wife. He repeatedly threatened Josephine with divorce because he believed that she couldn't give him one crucial thing: a male heir. The already disintegrating marriage would crumble in 1807, when a massive tragedy rocked the Bonaparte family.

Empress Josephine FactsNapoleon,France 2

23. He Humiliated Her

Napoleon's heir presumptive, his nephew Napoleon Charles, tragically perished of croup, leaving the Emperor without any successor. That's when Napoleon made a brutal choice. He needed an heir, and to get that, he needed a new wife. On December 14, 1809, Napoleon made history by divorcing his great love, Empress Josephine.

Napoleon and JosephineFlickr

24. She Didn't Take It Well

Apparently, when Napoleon told Josephine that he planned on divorcing her, she temporarily lost her mind. The devastated wife immediately fell to the palace's floors. She was literally paralyzed by shock, forcing Napoleon to carry her to her bedroom so that she could recover in privacy. But even in her chambers, Josephine couldn't hide her pain. Her wails echoed throughout the Tuileries.

Empress Josephine FactsNapoleon,France 2

25. Her Divorce Was Disturbing

Napoleon and Josephine's breakup was completely scandalous, and their chilling divorce ceremony didn't make things any more palatable. Even though the breakup had to happen, the couple was so distraught that they read statements of devotion aloud to each other as they signed the divorce paperwork. Josephine was so flustered that she couldn't finish her statement and needed someone else to step in on her behalf.

But the mixed signals only get murkier...

Empress Josephine FactsNapoleon,France 2

26. Her Loss Destroyed Napoleon

After contracting a horrible bout of pneumonia in 1814, Josephine passed on in Rueil-Malmaison of Paris. She was 50 years old. After learning of Josephine's demise, her ex-husband Napoleon responded with a heartbreaking gesture. Mad with grief, he locked himself in his room for two full days and refused to see anyone. Later, when he passed, her name was the last one on his lips.

He was definitely obsessed—but at least he had a healthy outlet for it. Not so with our next subject...

Napoleon Bonaparte FactsWikimedia Commons

27. Oskar Kokoschka Did NOT Take Rejection Well

When the artist Oskar Kokoschka came back from WWI, he arrived to the bummer discovery that his lover and muse, Alma Mahler, had married someone else. He then moved on like a functional adult. Just kidding: he commissioned a life-sized doll in her image. And it got even more bizarre from there. 

Oskar Kokoschka.Getty Images

28. He Was Fixated

Ordering a dollmaker to build it as realistic as possible—including fake tongue, teeth, and feathery skin to simulate softness—Kokoschka would pose and paint the doll in explicit positions. Nevertheless, even Kokoschka's relationship with his weird ex-girlfriend doll went south. He grew bored, decapitated the doll, doused it in wine, and threw it out the window. Can you believe the real Mahler dumped this catch of a man?

It's all pretty disturbing and gruesome, yes—but at least he was taking it out on a doll, not a real person. The same can't be said for Roman Emperor Nero...

History's Greatest RevengesWikimedia Commons "Portrait of Alma Mahler" by Oskar Kokoschka

29. Nero Was A Bad Lover To Cross

When you think of Emperor Nero, you probably imagine some of the worst debauchery, decadence, and bloodshed the Roman Empire ever produced. And to be honest, you’re not wrong. Did all of this bad behavior infect his romantic relationships as well? Oh, you bet. When his own mother disapproved of one of his mistresses (honestly, what did he expect?), he had her executed. His own mother.

The next target for his dirty tricks? His wife, of course.

Nero facts Nero (2004 TV Movie), Rai Fiction

30. He Was Ruthless

Does it count as a messy breakup if Nero circumvented the whole divorce thing by choosing murder instead? In 62 AD, he had his wife Octavia executed on the (probably false) grounds of adultery. One account of the story tells us that Nero couldn’t even get anyone to confess to sleeping with the Empress, so he bribed someone to confess as an excuse to kill her.

Nero facts Nero (2004 TV Movie), Rai Fiction

31. He Repeated The Pattern

Did Nero learn a lesson from this? Not at all. Next, he tied the knot with a woman named Poppaea Sabina. Poppaea was pregnant when she got into a fight with Nero, and in the heat of the moment, he kicked her in the belly. His attack took her life and that of her unborn child. At least this time, Nero mourned—but he did it in the weirdest way possible. Nero had one of the boys that he kept around castrated and then married him. The boy was said to have an uncanny resemblance to Poppaea.

Speaking of complete and utter perversion...ever heard of the Borgias?

Nero facts Quo Vadis (1951), MGM

32. When A Borgia Dumped Him, He Struck Back

It’s tough when no one in your family likes your partner, but at least they never tried to kill them in cold blood. Not so with Lucrezia Borgia, one of the more notorious members of the infamous Italian Renaissance family. Her relatives set her up with the politically useful Giovanni Sforza, but quickly changed their minds when his stock went down.

Lucrezia Borgia FactsFlickr

33. She Helped Him Escape

For some of us, this would mean a pretty bummer divorce. For Lucrezia’s trigger-happy family, it meant they had to violently dispose of their ex-son-in-law. Luckily, Lucrezia got wind of this plan and told Giovanni, who escaped Rome with his life. Unluckily, Sforza then paid his ex-wife back with some of the cruelest words in history…

Lucrezia Borgia factsThe Borgias (2011–2013), Showtime Networks

34. He Made A Disturbing Accusation

After finding themselves unable to stick Giovanni Sforza with the pointy end, the Borgias settled for trying to get him to sign an annulment. The ticked-off Giovanni took this opportunity to say "heck no," and then also accuse his ex-wife Lucrezia of a chilling deed: sleeping with her own father. Well, that’s one way to say goodbye. The Borgias finally got Giovanni on board by offering to give him Lucrezia's considerable dowry as compensation, but they are synonymous with the dark tale to this day.

What's worse, accusations of Oedipal love or Prince Charles' secret phone calls to Camilla? You be the judge...

Lucrezia Borgia factsThe Borgias (2011–2013), Showtime Networks

35. The Divorce Of The Century

We'd be remiss to make this list and not add the split that can rightfully be called "the divorce of the century"—that between Prince Charles and Princess Diana. They were the golden couple...or, at least it seemed like it. When the reality of their relationship came to light, people were absolutely shocked. And really, it all began long before they even met each other...

History's Worst BreakupsGetty Images

36. She Had An Unhappy Home

Diana did not grow up with a healthy idea of marriage. It was only as an adult that she revealed the extent of her parents' unhappy marriage and her own heartbreaking childhood. The Princess said that her parents divorced because of cheating and, even worse, physical mistreatment. After their marriage ended, Diana was sent away to boarding school. She was just 12 years old.

Princess Diana FactsFlickr

37. She Wasn't His First Spencer

Diana was first introduced to Charles, Prince of Wales in November 1977 through her older sister, Lady Sarah. Three years later, Charles began wooing Diana in 1980. The royal pair had Lady Sarah’s blessing, and upon their engagement, she remarked, "I introduced them. I'm Cupid". But that's not exactly the whole story. Sarah and Charles had a fling earlier on, meaning Diana got her big sis' sloppy seconds.

Princess Diana FactsGetty Images

38. It Was A Crowded Marriage

Despite Charles and Diana's beautiful wedding, their marriage would be marked by profound unhappiness. Charles was still strangely close to an ex-girlfriend named Camilla and, in one of the most notorious revelations about the royal family, the true nature of their relationship would be revealed to all. When Diana and Charles were still married, a mysterious person recorded a secret phone call between Charles and Camilla.

In it, they are frank about their attraction to each other, with Charles saying that he wants to be as close to Camilla as her tampons. Ouch and also, gross.

Prince Charles FactsFlickr

39. There Was A Sense Of Impending Doom

Only five years into the marriage of Charles and Diana, cracks began to show. The almost 13-year differences in ages between the two, plus Charles’ possibly-too-close friendship with Camilla Parker-Bowles became visibly damaging to their marriage. In a famous quip, Diana sadly said, "There were three of us in this marriage, so it was a bit crowded".

Princess Diana FactsGetty Images

40. She Stepped Out Too

As young Princess Diana struggled with her husband's infidelities, she sought comfort in the arms of James Hewitt, a cavalry officer. Hewitt and the Princess saw each other for five years between 1986 to 1991, but even after Diana confirmed the affair in an interview, the scandalous couple had more secrets in store. Hewitt was so devastated by their break-up that he contemplated taking his own life.

Even more controversial, to this day, people wonder if the redheaded Hewitt might be Prince Harry's father, though both Hewitt and Diana deny the idea.

Princess Diana FactsWikimedia

41. They Said "I Don’t"

You'd think that prim and proper Queen Elizabeth II would do everything in her power to prevent a messy, public divorce between her heir and his wife. Well, the media reports about both Charles' and Diana's infidelities was so bad, the queen was driven to her breaking point. She ended up writing each of them a letter with one chilling demand. The Queen urged Diana and Charles to get a divorce. By August of 1996, her will was done. The young couple went their separate ways after a notoriously stressful marriage.

Mostly, it seemed marked by sadness, instead of any contempt. The same can't be said for the Countess of Castiglione...

Princess Diana FactsGetty Images

42. The Countess Of Castiglione Was The World's Meanest Ex

Virginia Oldoini—known better to history as the Countess of Castiglione—was mad, bad, and dangerous to know. The Italian aristocrat’s legendary beauty and photographic misadventures turned her into the world’s first model, but that’s not what made her INfamous. Her bedroom exploits and passionate love affairs gone wrong are what make her story unforgettable.

Countess Castiglione FactsWikipedia

43. She Was A Child Bride

When Virginia was just 17 years old, her parents spent no time in marrying her off to Francesco Verasis, the Count of Castiglione. Although the union gave Virginia the name we know her by today, it didn’t give her a whole lot else. The count was 12 years older than the girl, and not much of a looker. But it only got worse.

Countess Castiglione FactsWikimedia Commons

44. She Stayed In Her Marriage For A Heartbreaking Reason

There was one, and just exactly one, bright spot in Virginia’s marriage to her fuddy-duddy count: Their son together, Giorgio. Oldoini doted on the boy as only a rich mommy can, pouring all her own frustrated hopes and dreams into him. Giorgio, in turn, adored her. Which makes the countess’ infamous act of revenge all the more savage.

Countess Castiglione FactsWikimedia Commons

45. Her "First Time" Was Scandalous

Right before her arranged marriage to the older count, Oldoini sowed her wild oats, and then some. The young girl reportedly embarked on a steamy affair with a hunky naval officer right before tying the knot, which suggests the soon-to-be notorious courtesan desired things beyond domestic bliss from the very beginning.

Countess Castiglione FactsWikimedia Commons

46. She Took Her Husband's Money

Before long, the Countess was caught up in a passionate affair with Napoleon III. And although infidelity is certainly close to #1 on the list of marital sins, the Countess of Castiglione didn’t stop there. Aside from taking up with Napoleon in full view of her husband Francesco, the countess also literally bankrupted the man with her expensive tastes. Hey, you think a face that beautiful comes for free?

Countess Castiglione FactsWikipedia

47. Her Count Abandoned Her

In 1857, barely a year after the well-heeled couple traveled to Paris, Count Francesco left court for his native Italy in a huff, leaving his young, impressionable wife behind. The separation wasn’t just an idle threat, either. He later scrawled furiously: "Our separation is irrevocable". As we’ll see later, though, Francesco wasn’t even done yet…

Countess of Castiglione FactsWikimedia Commons

48. Her Husband Tried to Punish Her

Sometime during her separation proceedings, the Countess of Castiglione’s estranged husband decided to ramp up the bitterness and do something truly horrific. He tried to claim custody of their only son Giorgio, using his wife’s lavish lifestyle as proof of her bad mothering. The countess’s response was swift and brutal.

Countess of Castiglione Facts Wikimedia Commons

49. She Gave A Cruel Payback

When Francesco tried to claim custody of her only beloved son Giorgio, the Countess of Castiglione didn't take it lying down. Instead, she sent her ex a "present" in the mail. When he opened it, he was horrified. It was a seemingly innocent photograph of the beautiful countess dressed up in a luxurious gown—but when the count looked closer, his blood ran cold.

Countess of Castiglione FactsWikimedia Commons

50. She Threatened Her Ex

Oldoini's photograph was a warning shot to her estranged husband: In the portrait, the well-dressed countess was also holding a knife in her hand, half-hidden in the folds of her dress. The best part? She titled the photo "La Vengeance," just to make her message extra clear. Wouldn’t you know, she got custody of Giorgio for the rest of his life.

Threatening a child is beyond the pale—but she obviously didn't act on it. Unfortunately for Wanrong, empress consort of China, her husband did...

Countess Castiglione FactsWikimedia Commons

51. The Last Empress Of China Lost Everything She Loved

When Wanrong became the Empress of China, she was already ruling over a ghost land. In a matter of months, her country abolished the monarchy, turning all Wanrong’s decadent pleasures into dust. Somehow, though, this was just the beginning of her tragic tale. By the end of her life, Wanrong would lose her husband, her crown, her child, and most infamously of all, her sanity.

Empress Wanrong factsWikimedia Commons

52. Her Family Wanted Her To Rule The World

In 1922, when Wanrong was still only 16 years old, the teenaged Emperor Puyi of China started looking for a bride. Although Puyi was technically not Emperor anymore, having been overthrown for the Republic of China in 1911, he was still allowed to live in stateliness and splendor in the Forbidden City. Accordingly, Wanrong’s ambitious family put her forward in a bridal bid…only, this was no fairy tale.

Empress Wanrong factsWikipedia

53. Her Emperor Was A Psychopath

In addition to his major case of rich kid syndrome, Puyi also had a terrifying dark side. He was notorious for his ruthlessness and loved to torment the eunuchs who served him. He particularly loved to flog the poor souls, despite repeated pleadings from his counselors to go easy on them. As Puyi himself later confessed, "My cruelty and love of wielding power were already too firmly set for persuasion to have any effect on me". Run girl, RUN.

Empress Wanrong factsThe Last Emperor (1987), Columbia Pictures

54. Their Wedding Night Was Disturbing

Wanrong's marriage to Puyi seemed doomed from the start. He had little interest in her, and he even married a secondary bride on the same day he made Wanrong his official consort. After both wedding ceremonies were over, the two brides and the Emperor made their way over to the Palace of Earthly Tranquillity inside the Forbidden City.

This is where Emperors had traditionally consummated their marriages in the domineering Dragon Bed, and Puyi now had not one but two blushing brides on his mattress. That’s when it took a bizarre turn.

Empress Wanrong factsThe Last Emperor (1987), Columbia Pictures

55. She Repulsed Her Husband

It’s a matter of official historical record that when Emperor Puyi gazed upon Wanrong and Wenxiu, he…turned tail and ran like the dickens out of the room. Now, this is somewhat to be expected—and even preferred—given that they were all a bunch of inexperienced teenagers. But historians suggest an even more unsettling reason for Puyi’s actions.

Empress Wanrong factsThe Last Emperor (1987), Columbia Pictures

56. Her Emperor Had Violent Tastes

Today, many experts believe that Emperor Puyi harbored gay or bi desires, but was forced to display more culturally acceptable tendencies. Which, well, would suck. But don’t go getting too empathetic for the guy: Puyi liked to show his love by hiring and then sodomizing pageboys, and he also had a really big thing for very young girls, which explains the 12-year-old concubine.

Yep, this was the guy Wanrong married. I mean, how could it get worse? …Right?

Empress Wanrong factsThe Last Emperor (1987), Columbia Pictures

57. She Was Pushed To Her Limit

In truth, Wanrong was suffering from her own issues without taking on her husband’s baggage. The Forbidden City was a stifling, formal nightmare, and the young girl had to learn a litany of new rules, traditions, and etiquette to keep up with what the court expected. Things began to unravel—and fast. Around this time, the still-teenaged Wanrong started using opium as a casual habit.

It was widely accepted at the time—but that didn't mean that it didn't go wrong for her. To make matters worse, a coup exiled the couple from the Forbidden City. Puyi then moved them to Japan...and straight to their breaking point.

Empress Wanrong factsWikimedia Commons

58. She Tried To Flee

Poor Wanrong was seriously reconsidering her commitment to her marriage, so much so that she attempted to become a runaway Empress and flee from Manchukuo. Uh, multiple times. Practically any official who happened to come to the state around this time got a desperate visit from the consort, begging them to secret her out. If only she had escaped, her fate might have been much different.

Empress Wanrong factsWikimedia Commons

59. She Betrayed Her Husband

When all her chances for freedom and happiness slipped from her fingers, Wanrong rebelled in a much more scandalous way. Bored and lonely, the Empress struck up an affair with two of Puyi’s aides, a man named Li Tiyu and another named Qi Jizhong. I mean, it wasn’t like Puyi was paying attention to her.  But as anyone could tell you, our girl was playing a dangerous game.

Empress Wanrong factsThe Last Emperor (1987), Columbia Pictures

60. She Had A Secret Love Child

In 1940, Empress Wanrong received utterly shocking news. After years of her childless and icy marriage, she was pregnant…and the baby was most certainly not Puyi’s. Instead, one of her steamy dalliances with Li Tiyu had landed her with a bun in the oven, and now the Empress had to face the music. What ensued was a tragedy worthy of the opera.

Empress Wanrong facts Wikimedia Commons

61. Her Daughter Suffered A Horrible Fate

Instead of helping out his wife in any way, Emperor Puyi committed one of the most horrific betrayals in Chinese history. The moment the baby, a little daughter, was born, the Emperor ignored Wanrong’s wishes entirely, and instead had his aides snatch the girl from her mother’s bosom and then kill the newborn. Yes, really. And he wasn’t finished.

Empress Wanrong factsThe Last Emperor (1987), Columbia Pictures

62. Her Husband May Have Told Her A Huge Lie

According to one version of events, Puyi never even told Wanrong about the true fate of her baby. Right after her childbirth, he whisked her away to the hospital without her daughter, and when she came back, he lied and said that he was having an outside nanny look after the newborn. Thing is, this option is so much better than what really might have happened…

Other sources claim that instead of keeping the truth from Wanrong, Puyi mercilessly let it all hang out. The Empress’s response was gut-wrenching.

Empress Wanrong factsWIkipedia

63. The Truth About Her Daughter Broke Her

Riddled with grief over the loss of her innocent child, some people say Wanrong gave in completely to opium, existing in a numbed state for the rest of her life. That life would not last much longer. Puyi abandoned her, and she attempted to flee to Korea only to have authorities throw her in prison. There, she finally expired from malnutrition and the effects of her withdrawal from opium.

Living in exile does not do a girl well—and Wanrong's sad end is up there with the tragic fate of Korea's last princess, Deokhye...

Empress Wanrong factsThe Last Emperor (1987), Columbia Pictures

64. The Tragic Story Of Korea’s Last Princess

We often imagine princesses leading charmed lives filled with romance, adventure and riches. However, this was not the case for Deokhye, the last princess of Korea. At a young age, she endured discrimination, exile, and the loss of her parents. People in Korea adored her, but her Japanese captors hoped to quell her power as a symbol for her people. One of the ways they did this was by engineering her marriage.

On the surface, it seemed like a fairy tale: She was a beautiful princess, and her betrothed was a handsome count. But behind the scenes, it was an actual nightmare.

Princess Dukhye factsWikipedia

65. Her Marriage Was Extremely Unhappy

Deokhye suffered from schizophrenia, and the constant upheaval of her early life didn't exactly send her on the path to happiness and stability. Still, at first, her husband Count Takeyuki tried to make her happy despite the circumstances. Eventually, a dark reality set in. The treatment for her mental illness was incredibly expensive, even for a pair of nobles. She was frequently institutionalized, and she missed some of their daughter's formative years as a result.

Japan's loss in WWII made things even more dire, as the Count lost his noble title in its aftermath. But the worst was yet to come...

Princess Dukhye facts Wikimedia Commons

66. Her Husband Gave Up

In the end, the Count called time on his marriage to Deokhye. They’d had a few good years together, but for the most part, these two had been unhappy for a very long time. The pair called it quits eventually and got a divorce in 1953. At that time, any divorce was going to be scandalous—but the Count and Deokhye's break-up was more dramatic than most...

Princess Dukhye factsWikipedia

67. Her Husband Dumped Her In The Cruelest Way Possible

Count Takeyuki dumped poor Deokhye in the worst possible way. He did it while she was in the hospital undergoing treatment for her plummeting mental health. So much for tact! And to pour salt on his ex-wife's wounded heart, the Count struck up another romantic relationship very soon after leaving Deokhye in the hospital. Yeesh. He may have moved on, but things weren't so easy for Deokhye...

Princess Dukhye factsThe Last Princess (2016), Hofilm

68. Her Daughter Disappeared

Deokhye’s life was continuing to spiral downwards as she endured her divorce and constant hospitalizations, but at least she took some relief from the fact that her daughter was doing very well. She graduated from university with a degree in literature and got married in 1955. However, in the end, both Deokhye and her daughter couldn’t escape the curse of unhappiness...

Now we come to one of the most jaw-dropping parts of Princess Deokhye’s already dramatic life. One day, Deokhye’s daughter just up and disappeared.

Princess Dukhye factsThe Last Princess (2016), Hofilm

69. She Couldn't Recover From It All

As the days turned into weeks, the hope that Masae would reappear at home started dwindling. After enough time passed, Deokhye had to accept that her daughter would never return—for a tragic reason. Many people believe that Masae took her own life, driven by grief over her parents' divorce. Then, for awhile, Deokhye herself disappeared.

When the new South Koren government found her, she was in a mental hospital. Though she was finally able to return home after 38 years in exile, she was never the same. Exile and struggle also marked the story of one of the Middle Age's worst splits, that of Matilda of Tuscany and her ill-fated husband...

Princess Dukhye factsThe Last Princess (2016), Hofilm

70. Matilda Of Tuscany Brought Her Husband To His Knees

Many of these breakups are so brutal precisely because they came from a once beautiful and loving relationship. Not so with Matilda of Tuscany. She was already a powerful warrior in her own right when her stepfather arranged her marriage with his son, Godfrey the Hunchbacked. She eventually acquiesced in order to protect the papacy in Rome. Unfortunately, Matilda and her new husband just didn’t have much in common.

They differed in matters of religion, and his physical deformity only fueled their dislike of one another. The two always seemed on the verge of calling it quits, until a family tragedy finally tore them apart. 

Matilda of Tuscany FactsGetty Images

71. He Wouldn't Let Her Go

Matilda became pregnant and gave birth to a little girl around 1071. Sadly, the baby only lived for a few weeks. The heartbreaking event drove an even deeper wedge between Matilda and her husband, and eventually, Matilda separated from him entirely. She returned to her mother, and began strengthening her ties to Italy. He found her, hoping to reconcile, but she told him she wanted a divorce and to become a nun.

He then made a deal behind her back to ensure that they'd never be granted their divorce. And then, he added insult to injury.

Matilda of Tuscany FactsGetty Images

72. He Lied About Her

Godfrey's betrayal left Matilda smack dab in the middle of an ongoing battle between the Pope and the Holy Roman Emperor. Many believe that Godfrey was also the source of a rumor about an affair between Matilda and the Pope—one that could've had devastating consequences. However, before she could respond, Matilda finally got to see karma strike her detestable husband down.

Matilda of Tuscany FactsWikipedia

73. Someone Took Out Her Husband

On February 27, 1076, Matilda’s husband was—ahem—"answering the call of nature" when someone ran him through with a spear. All fingers immediately pointed to Matilda, who had every reason to hate her husband. Since Matilda wasn’t present at the time, and couldn’t have known about the accusations he'd made yet, this was unlikely. Still, his loss left her even more stuck in between the ongoing struggle between the Pope and the Emperor—one that would sadly plague her for the rest of her life and lead to the dissolution of her family's realm.

And it all started with one Medieval fix-up gone wrong! If only they'd learned a lesson here. Three centuries later, the English throne came under threat thanks to a similar—if even more toxic—mismatch.

Matilda of Tuscany FactsWikimedia Commons

74. Edward And Isabella Truly Hated Each Other

When the handsome King Edward II of England married the beautiful Princess Isabella of France, people called it a fairy tale—but it was really a horror story. See, Edward II already was way more interested in someone else: his BFF and courtier Piers Gaveston. Edward and Isabella finally pulled the trigger after a long engagement (one his father tried to get him out of) in 1308.  It quickly turned into a disaster.

In a disturbing portent for their entire marriage, Edward decided not to sit next to his child bride at the ceremony, but cozied up to Gaveston instead. The snub insulted Isabella’s entire family in one fell swoop. Iconique. Oh, and there’s a kicker.

Edward II factsBritain

75. He Turned On Her

It's not like Edward's fondness for Piers pleased his own people, either. Their relationship caused a crisis among his barons, who then executed Piers. Instead of say, learning a lesson, Edward took up with another man, Hugh Despenser the Younger. When his barons then had that side piece exiled, Edward used his own wife as bait in a plot to punish his so-called enemies. With that cruel betrayal under his belt, he upped the ante. He turned his contempt toward Isabella herself—and it was not pretty.

Edward II factsBritain

76. His Marriage Fell Apart Spectacularly

By 1324, Isabella and King Edward’s relationship had deteriorated beyond repair, and Edward sure let her know it. Partly using rising tensions with France as an excuse, he confiscated all of Isabella’s lands, took over her household, and threw her French staff behind bars. As a rotten cherry on top, he then ripped the Queen’s children from her bosom and dumped them with the Despenser clan to get a "better" childhood.

Ouch. Is it any wonder Isabella got her husband back so brutally?

Edward II factsBritain

77. His Queen Rose Up Against Him

Edward might have been notoriously good at getting revenge, but Isabella had learned a thing or two from her husband. By September of the same year, Isabella’s teenage son Prince Edward had joined her in France—and that’s when she pounced. Holed up in enemy territory with the heir to the English throne, Isabella's plan kicked into gear.

First, she refused to come back to her husband. She also began to publicly mourn her marriage, claiming Hugh Despenser had destroyed it. And she didn't stop there...

Edward II factsBritain

78. His Queen Slept With The Enemy

By February 1326, King Edward’s long-suffering wife was thoroughly done with him, and her final nail in the coffin shot right through his heart. While over in France, Isabella started up an affair with the handsome English courtier Roger Mortimer, who just so happened to be one of Edward’s exiled foes. Yep, Isabella was sleeping with the enemy…and big trouble was brewing.

She also arranged to marry off her son and in return, got a fleet of warships. Gee, what could she need those for?

Edward II factsBritain

79. He Had A Brutal Downfall

Within months, the vengeful queen’s forces had captured and imprisoned Edward and Hugh. Isabella sentenced Hugh Despenser to execution—specifically, she wanted him disemboweled, castrated, and then quartered. And that wasn’t even the worst part. The massive crowd that turned up to Hugh’s execution also watched as people wrote Biblical verses about corruption and arrogance all over his bare skin.

Then, when all was said and done, they hung his limp body. Next, she had her husband Edwad to deal with.

Edward II factsWikipedia

80. He Was In A Stalemate

Isabella couldn't exactly just execute him the way she had Hugh. Instead, she imprisoned him, and a group of courtiers convinced him to abdicate the throne to his son, who became Edward III. Less than a year later, attendants found his lifeless body in his cell. He was only 43. The cause was unknown, and people obviously whispered about Isabella's role in all of this...what's that saying about a woman scorned?

Perhaps Isabella's plot to escape an unhappy marriage inspired Queen Caroline of Denmark, four centuries later. After all, she was in a similar situation—but her plan didn't quite work out the same way Isabella's did.

Edward II factsBritain

81. Queen Caroline Lived Scandalously...And Paid For It

The short life of Queen Caroline Matilda had it all: a royal marriage, love affairs, court intrigue, masquerade balls, brutal exiles, and heinous executions. The British-born, Danish-crowned royal was one half of an 18th-century power couple—or so it seemed. Upon close examination, her betrothed, King Christian VII, wasn't exactly all he was cracked up to be...

Queen Caroline facts Wikipedia

82. Her Husband Was A Dud

King Christian VII suffered from mental illness early on in his life and modern scholars believe that he was schizophrenic. The Danish court hastily arranged his marriage to Caroline Matilda because they believed that a wife would improve his mental condition. Romantic! And that's not all. He was already indulging in an ongoing affair when he got engaged—one which he didn't exactly break off.

When they did finally tie the knot and settle down in Denmark, he kept seeing courtesans. On top of that, the King was deeply uninterested in his bride and treated her "coolly" even in the early days of their relationship.

Queen Caroline facts Wikipedia

83. She May Have Had A Summer Romance

Both the royal court and the Danish people straight up did not like Caroline and treated her like trash. She had few people to turn to—and even fewer, after her husband sent away one of her closest friends. Then, King Christian VII departed Copenhagen for a European tour in the summer of 1768, leaving his wife and their child behind. Instead of moping, Queen Caroline allegedly used the opportunity to indulge in what we now call a "hot girl summer".

Some claimed that, the moment her husband’s European tour began, Caroline started an affair with a handsome actor named La Tour.

Queen Caroline facts A Royal Affair (2012), Zentropa Entertainments

84. Her Husband Exiled Her Boyfriend

Christian VII returned to Denmark after his European tour and immediately learned of the rumors of his wife’s infidelity. The veracity of those rumors is still uncertain but one thing is crystal clear: the King wasn’t happy. Christian VII exiled La Tour from Denmark based on speculation alone. But he'd also brought along another souvenir: the German physician and philosopher, Johann Friedrich Struensee.

Struensee became the king's official Royal Physician because he was good at dealing with the King’s mental issues. Struensee and Caroline got off to a rocky start, but before long, they'd warmed to each other. Perhaps too much...

Queen Caroline facts A Royal Affair (2012), Zentropa Entertainments

85. She Began An Affair

There were only rumors that Caroline had carried on an affair with the actor La Tour. But it is fact that Caroline and Struensee became romantically involved in the spring of 1770—less than two years after Struensee had arrived in Copenhagen. And they weren’t shy about their affair. In fact, pretty much everyone knew about it, including her family back in England.

Caroline and Struensee began to work together to play a game of real-life chess with the Danish courtiers, expelling those they didn't like and promoting those they did. Then, she got pregnant...

Queen Caroline facts A Royal Affair (2012), Zentropa Entertainments

86. She Was The Subject Of Fake News

When Caroline gave birth, people speculated that the child was Struensee's and that the pair planned to assassinate King Christian VII. His stepmother even received false evidence about a plot to overthrow the king. Fake or not, the evidence had a devastating effect. Juliana Maria had Caroline Matilda detained in January of 1772 and "imprisoned" in an honest-to-God castle. But even in her palatial "cell," Caroline Matilda couldn’t escape the court.

Queen Caroline facts Wikimedia Commons

87. She Had Her Marriage Dissolved

Caroline Matilda and Struensee finally confessed to their romance during an interrogation. The Church of Denmark promptly dissolved the marriage between Caroline and Christian VII. Mercifully, they also absolved Caroline Matilda of any moral wrongdoing. Struensee, on the other hand, faced a far darker fate. The Danish court sentenced the disgraced Royal Physician to the guillotine. As for Caroline, she mourned in exile.

Later, she plotted a coup against her ex, Christian VII, only to succumb to scarlet fever before she could enact her plan. She was only 23. Caroline's youthful forbidden romance had gotten her into all kinds of trouble—a pattern that would be repeated centuries later by another royal.

Queen Caroline facts Wikimedia Commons

88. The Man Who Broke Princess Margaret's Heart

As anyone who has watched The Crown can attest, royal watchers in the post-WWII era were absolutely obsessed with Princess Margaret's prospects for marriage. She had an absolutely disastrous forbidden romance with an RAF officer named Peter Townsend that left her heartbroken and her sister furious. After that, Margaret rebounded hard with a talented young photographer named Antony Armstrong-Jones. It seemed like she'd finally get her happily ever after—but sadly, nothing could be further from the truth.

Princess Margaret factsA Tale of Two Sisters (2015– ) Queen Elizabeth II and Princess Margaret, 3DD Productions

89. People Disapproved Of Him

Though the wedding of Tony and Margaret was extremely popular, some people in the British press did not approve. They believed that it was improper of a princess to marry a "commoner" like Tony, even though he had proved to be an extremely accomplished individual. Servants also sometimes treated him rudely, because he wasn’t "equal" to the other royals. That must have been a lot of pressure on was only a matter of time before cracks started to show.

GettyImages-695412.jpgGetty Images

90. They Both Strayed

In 1966, the British newspaper The Telegraph reported a shocking story: They claimed Armstrong-Jones carried out an affair during a business trip abroad. Sounds like your run-of-the-mill tabloid gossip today, but back then, the rumor was utterly scandalous. Soon, his wife Margaret got wind of it, and she decided that two could play at that game. She took a few lovers of her own.

This was the beginning of many years of back-and-forth cheating between the two of them. And pretty soon, it got real ugly.

Antony Armstrong-Jones, The Earl Of Snowdon factsWikimedia Commons

91. She Ran Off With A Gardener

In 1973, Princess Margaret ran off with a gardener named Roddy Llewellyn. Not only was Roddy a common gardener, but he was 17 years younger than Margaret! And this wasn’t just a side fling either—their romance lasted for eight years. This affair only served to escalate the battle of Tony vs. Margaret even further. If you think things are getting out of hand now, know that these two were just getting started.

Princess Margaret factsGetty Images

92. He Entered A Long Term Relationship Of His Own

When Tony heard about Margaret’s dalliance with the gardener, he was livid. He decided that the best strategy was to continue to escalate the conflict with his wife. In 1977 he started seeing a journalist named Ann Hills, who remained his mistress until 1996—but that was hardly his worst transgression against Princess Margaret. No, that would only come out later, after their divorce...

Princess Margaret, The Countess of Snowdon factsGetty Images

93. He Was Unfaithful From The Start

The public watched Antony Armstrong-Jones' marriage to Princess Margaret fall apart in front of their eyes—but it actually started way earlier than anyone realized. While both Tony and his wife hit each other below the belt, Tony clearly instigated the whole thing. In 2004, DNA testing proved that he had an illegitimate daughter, who was born just weeks into his marriage with Margaret.

The identity of the girl’s mother was even more shocking...

Antony Armstrong-Jones, The Earl Of Snowdon factsA Tale of Two Sisters (2015– ) Queen Elizabeth II and Princess Margaret, 3DD Productions

94. He Slept With His Best Friend’s Wife

The 2004 DNA test revealed that a British woman named Polly Higson was Tony’s daughter, and that she was born during his honeymoon with Margaret. What’s really scandalous though is that Polly’s mother was Camilla Fry, the wife of Tony’s best friend. Tony just couldn’t keep his hands off of anyone! It was a small blessing that Princess Margaret had already been gone by the time the news came out—that is, if she didn't already know about it. Yikes. 

Antony Armstrong-Jones, The Earl Of Snowdon factsWikimedia Commons

95. The Heartbreaking Tale Of Queen Soraya

In certain corners of the world, someone only has to whisper the name "Queen Soraya" to conjure up a story of sweeping beauty, royal betrayal, and lasting tragedy. From a teenage marriage to her mysterious end in a Paris penthouse, Soraya Esfandiary-Bakhtiary’s heartbreaking life is worthy of a twisted fairy tale. There’s a reason they called her "the sad-eyed princess"...

Queen Soraya facts Wikimedia Commons

96. They Fell In Love At First Sight

Soraya's legendary beauty brought her straight to the palace gates, and when she was still in her teens, her parents betrothed her to Iran's shah, Mohammad Reza. He was 12 years her senior. Despite the age difference and his extremely dysfunctional family, the pair were instantly enchanted with each other. However, those two problems would become the least of their worries...

Queen Soraya facts Getty Images

97. She Got A Devastating Diagnosis

After they tied the knot, Soraya was under great pressure to produce an heir for her husband and when she hadn't gotten pregnant after three years of marriage, they both knew something had to give. With a sense of dread, the Shah asked Soraya to travel to America for a medical check-up. The results were heartbreaking.

While one doctor gave her a clean bill of health and claimed stress was the problem, another told her that she was completely infertile. Devastated, she returned to Iran to deliver the news.

Queen Soraya facts Getty Images

98. Her Husband Made an Indecent Proposal

Knowing that Soraya would likely never bear him children, the Shah came up with an unsettling solution to their Great Matter: He proposed taking a second wife. When the jealous, volatile Queen Soraya heard the Shah’s brilliant plan, what do you think her reaction was? She rejected it point-blank…and made her own strange suggestion. She suggested that he change the constitution so that he could pass the crown to a half-brother.

A back and forth followed, but as each day passed, it seemed less and less likely they'd be able to reach an agreement...

Queen Soraya facts Wikipedia

99. Her Divorce Was Heard Round the World

In March 1958, Soraya crossed a boundary she could never take back. Marital negotiations between her and the Shah broke down completely. On March 14, Iran officially announced that the royal couple was divorcing and that Soraya would no longer be the queen. Yet that was the public show…it was much different behind closed doors. Soraya, who had been living in Europe away from the Shah at the time, claimed that she was all but blindsided by the announcement.

Still, their heartbreaking story didn't end there.

Queen Soraya facts Soraya (2003 TV Movie), Rai Fiction

100. She Couldn’t Move on

Soraya and the Shah just couldn’t quit each other. Everybody knew the Shah was still in love with his ex-wife, and they reportedly met several times after the divorce. Even after he remarried, she kept him in her heart. Sadly, in 1979, Soraya received some shocking news. Her ex-husband the Shah was now dying of cancer, with absolutely no hope for recovery.

So after more than 20 years apart, Soraya wrote him a letter. Its contents were heartbreaking.

Queen Soraya facts The three faces (1965), Dino de Laurentiis Cinematografica

101. She Requested a Secret Meeting

In her heartfelt letter to the Shah, Soraya exposed her deepest secret: She still loved him, and she had never stopped loving him. But Soraya didn’t leave him with just words. She also swore that if he would have her, she wanted to see him one last time before he passed. All that was left to do was wait for the Shah's reply. Mohammad Reza confessed that he, too, had never stopped loving her, and that he was desperate to say goodbye to her in person.

Sadly, this never happened. He passed on before the star-crossed lovers could manage to arrange a meeting. How's that for an unhappy ending?

Queen Soraya facts Wikimedia Commons

Sources:  1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17

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