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Breaking Up Is Hard To Do: Facts About History’s Worst Splits And Divorces

Penelope Singh

Breaking up is hard enough as it is—so imagine how bad it must be if, for example, you’re a king in the middle of a succession crisis, an Old Hollywood star under a morality clause, or a vulnerable mistress to a devious and powerful aristocrat. Nowadays, all it takes is a text message to get out of a bad situation, but these stories ripped straight from the history books really take “heartbreak” to the next level. Light a torch for these facts about history’s worst breakups, separations, and divorces. 


1. Hello, Dolly

Artist Oskar Kokoschka had a hot and heavy affair with a beauty named Alma Mahler, who then let him down gently by saying she just loved him too much to continue it (heard that one before, Alma). In response, Kokoschka did what any heartbroken soft boy would do. He commissioned a life-sized Alma doll complete with fake teeth and feathery skin, natch.

Nevertheless, even this relationship went south, as Kokoschka 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?

2. No Wonder She Became Bloody Mary

Mary I, commonly known as Bloody Mary, was the eldest child of Henry VIII and his first wife, Catherine of Aragon. She was declared illegitimate when her father divorced her mother and sent her away. Mary and Catherine weren’t allowed to see each other because they refused to acknowledge the new Protestantism or Henry’s new queen, Anne Boleyn.

As if that weren’t bad enough, Mary wasn’t even allowed to attend her mother’s funeral when she died. Safe to say she grew up with a few grudges.

3. Ding Dong, the Witch Is Dead

King Henry VIII was desperate to have a male heir, so when his first wife Catherine of Aragon couldn’t give him one, he did what any insane ruler would do: Create a new religion so that he could get a divorce. Once that was done, he promptly married his second wife Anne Boleyn.

4. Equal Opportunity Execution

In the days when Henry VIII was getting ready to burn all the bridges in the world by divorcing his wife to marry Anne Boleyn, one woman turned to prophecy to stop him. In 1532, a Catholic nun (and mystic) named Elizabeth Barton prophesied that if the King married Anne Boleyn, he would die and go to Hell. She was promptly arrested by the next year and forced to admit that she’d made it all up (which, let’s be fair, she probably did).

Barton was beheaded for her treason and her head was put on a spike on London Bridge. She remains the only woman in history to have her head decorate the bridge.

5. Date Tip: Go To Your Parent’s Grave

There’s plenty of ghoulish facts to mine about poet Percy Bysshe Shelley and Frankenstein author Mary Shelley. Most will cite their early “romantic” sojourns to her mother’s grave and their star-crossed love that was against her father’s wishes, forcing them to run away with each other. But that’s just the beginning of their nightmarish relationship. 

6. Can’t Water Down the Truth

When Percy Bysshe and Mary Shelley began their relationship, Percy was already married—and his wife was found very pregnant and very drowned to death just weeks before Godwin and Shelley finally wed each other. By most accounts, her tragic death was a suicide, but that’s still an unbelievably grim start to an otherwise productive literary union.

7. Severance Payback

The love story of Heloise and Abelard is one of history’s great Romeo and Juliet tales, except with a whole lot more castration. The pair met when Heloise was a young, brilliant scholar and Abelard was her tutor. Happily ever after, right? Wrong. Heloise’s uncle didn’t take kindly to the match, and after the two were married in secret, he gave them a gruesome wedding “present.”

He and his friends broke into Abelard’s room one night and castrated him, severing the union and, obviously, other parts. Welcome to the family, bro.

8. Beauty and the Beast

In the 17th century, there was a no bachelorette more eligible than Hortense Mancini, a renowned court hottie with a butt-load of money. So when Hortense married the equally wealthy Armand-Charles, the Duke of Meilleraye, it seemed like a match made in rich white people heaven. Except it wasn’t. It was an absolute waking nightmare.

9. Udderly Outrageous

You see, Armand was a veritable nut job. He jealously searched Hortense’s room for lovers, refused to allow his female servants to milk cows because it was too sensual, and often knocked out said servants’ teeth to make them look less attractive. Hortense, it hardly needs to be said, was absolutely miserable—so she came up with an ingenious plot.

10. The Runaway Duchess

In 1668, Hortense Mancini escaped her husband’s clutches by leaving her children and running clear away, an act of rebellion that was just not done at the time. It didn’t help that while gallivanting about, she loved drinking and dressing like a man. Now free from her tyrannical husband, Hortense quickly became famous all across Europe as “The Runaway Duchess.”

She was finally free, but it wouldn’t last for long. 

11. Together Forever

Sadly, Armand-Charles had the horrific last laugh when it came to his ex Hortense. After she died, knee-deep in gambling debts, the ever-watchful Armand punished her brutally. Her debtors were selling off her remains (ew, in so many ways), so Armand purchased his ex-wife’s corpse and paraded it around France for months.

12. You Drive Me Crazy

Anne Lister, AKA Gentleman Jack, was the first modern lesbian. She was also a total rake, leaving a trail of broken hearts behind her as she went through the 19th century. While in school, she fell in love with a girl named Eliza, and the pair swore they’d be together forever. Instead, Lister dealt Eliza an absolutely cold-hearted betrayal.

She soon started a series of relationships with other schoolgirls, and Eliza was so devastated that she had to be committed to a sanatorium.

anne listerWikimedia Commons

13. Unhappy Home

Princess 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 abuse. After their marriage ended, Diana was sent away to boarding school.

She was just 12 years old.

14. 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.

15. Her Secret Battle

Princess Diana was one of the first celebrities to reveal that she struggled with an eating disorder. When the Princess explained her years with bulimia, she described the mental illness as a “symptom” of a much bigger problem: Her loveless marriage and how unhappy it made her. For Diana, at her lowest points she felt like she wasn’t “worthy or valuable,” which led her to seek comfort in bingeing and purging.

16. Up in Flames

As young Princess Diana struggled with her husband Princes Charles’ 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 suicide. 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.

17. “I Don’t”

Diana’s marriage to Charles was extremely strained, and the media began reporting about both of their infidelities. Queen Elizabeth wrote 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.

18. Ouch

When Charles and Diana were divorced, Diana was stripped of her “royal highness” status. This meant she had to curtsy to those who had it, including her own children.

19. All the Boys Love Diana

After her divorce, Diana dated a few big-name celebrities including John Kennedy Jr. and the singer Bryan Adams. However, it was the Pakistani surgeon Hasnat Khan who became the love of her life. Diana called him “Mr. Wonderful” and he broke her heart when he decided that life in the royal family would make him too miserable to continue their relationship.

20. No Love Lost

After Henry VIII basically invented divorce to get rid of Catherine of Aragon and marry Anne Boleyn, his second wife showed no lack of disdain for her predecessor. Boleyn refused to attend Catherine’s funeral, and spent the day parading around the castle in bright yellow. Rumors spread that Anne had threatened to murder Catherine and her daughter Mary, and Catherine’s death led many to suggest that Anne had finally made good on her threat.

21. Heart of Darkness

For its time, Catherine of Aragon’s cause of death was ambiguous. Her embalmer noticed the corpse was in perfect health—save for her heart, which had turned black. That led some people to whisper about poison. Today, historians agree generally agree that Catherine died of heart cancer, which—considering the circumstances of her life—appears too poetic to be true.

22. Going out Like a Queen

Sadly, as we now know, things went south fast with Henry and Anne Boleyn. After she, too, failed to give him a bouncing baby boy, Henry made Catherine’s fate look like child’s play. He sentenced Boleyn to death for treason and adultery, and on May 19, 1536, she faced her executioner. In a final act of rage and/or guilt, Henry had all likenesses of his second wife destroyed.

23. Famous Words

The most famous quote by Anne Boleyn was spoken just prior to her execution. She reportedly was chatting with someone about her executioner and, in an attempt to reassure her friend, said “I hear he’s quite good. And I have a very small neck!”

24. Annus Horribilis

The marriages of Queen Elizabeth II’s three divorced children all saw a terrible time in the year 1992. Prince Andrew and Sarah, Duchess of York, along with Princess Anne and her husband Mark Phillips, were all dragged through the media by tabloids, which in Britain can be even more sensational than those in the US. That was the same year that the affair between Prince Charles and Camilla Parker-Bowles as well as his wife Princess Diana’s infidelities were much-publicized.

In addition, on November 20, 1992 (the Queen’s wedding anniversary) a fire broke out in Windsor Castle, the Queen’s residence, causing extensive damage. Elizabeth would later refer to 1992 as annus horribilis, Latin for “horrible year”.

25. From Temp to Permanent Position

The most powerful mistress of the French King Louis XIV was clearly Madame de Montespan. She rose to chief mistress (maistresse-en-titre) by cultivating a friendship with his current chief mistress, Louise de La Vallière, and then swooping in to “temporarily” fulfill her friend’s “duties” when both Louise and the queen found themselves pregnant.

To make rejection a little less embarrassing for La Vallièrehe did (at first) keep the women in the same apartments, so he could visit Montespan without drawing suspicion. What a gentleman.

26. Roommate Drama

King Louis’s transition period from de La Vallière to Montespan was awkward for all involved. At first, he made his discarded lover (La Vallière) and current lover (Montespan) share an apartment. Both Louis and Montespan were married (to other people), so they were committing double-adultery. This arrangement was so Louis could visit his new squeeze without arousing the suspicion of Montespan’s husband.

We’re not sure how La Vallière reacted…

27. Cheaters Never Prosper

From 1677 to 1682, a large ring of poisoners—and poison profiteers—was uncovered in France in what became known as the Affair of the Poisons. Most scandalously, many of the clients and collaborators implicated in the charges were members of the French aristocracy itself. One of the fingers pointed right next to the king: Madame de Montespan was accused of using these illegal wares to poison her romantic rivals, thus keeping the king’s eyes on her.

28. These Violent Dances Have Violent Ends

In 1679, Montespan was accused of using witchcraft and aphrodisiacs to stay ahead of King Louis’s other lovers. A midwife named Catherine Monvoisin, or La Voison, had been arrested as part of the Affair of the Poisons—and she had named the king’s chief mistress as one of her prolific clients. La Voison even alleged that Montespan performed black masses, a sacrilegious accusation that effectively destroyed Montespan’s reputation, regardless of the truth.

29. Love Juice

In the specifics of La Voisin’s accusations against Montespan, the midwife alleged Montespan and a witch would call on the Devil to ensure the king’s love in his mistress. To seal the deal, they also sacrificed a newborn baby and used the blood and bones in a love potion for the king. It was said that the king’s food was poisoned for 13 years to keep his heart—and other parts—in line for her. Bon appetit!

30. Not Your Mom’s Cabbage Patch Kids

It’s said that police up dug 2,500 baby corpses in La Voisin’s garden, all of whom were used in Montespan’s black mass love rituals. Of course, this is almost definitely a myth or exaggeration, as no contemporary evidence of such a mass grave exists. Either way, the news absolutely rocked the French courts, and Louis XIV dropped Madame de Montespan like a hot potato.

She was exiled to a convent, and when she eventually died, her children with the king were not allowed to mourn for her.

31. Room with a View

It’s said that the wife of the French King Henri II, Catherine de Medici, bored peepholes into the roof of his mistress Diane de Poitiers’s bedchamber so that she could see him “in action” with his side piece. She apparently noted the contrast between the disinterested performance she got from Henri versus the “spectacle” he gave Diane.

Listen Catherine, insecurity like that is just downright unhealthy. Pick yourself up, sister!

32. Creative Conception

After a decade of royal infertility, the physician Jean Fernel noticed slight “abnormalities” with Catherine de Medici and Henri II’s sexual organs. That must have been a fun conversation. Imagine telling a pair of absolutely powerful royals that their junk looks strange. Anyway, he advised them with “positions” to take…and it appeared to work.

The couple went on to have ten kids, which is a good number by anybody’s standards. Jean Fernel must have been thanking the gods.

33. Our Lady of Vindication

Catherine de Medici was cordial to her husband’s mistress…during his lifetime. As Henri lay dying from a jousting accident, her true feelings revealed themselves. Catherine denied Diane de Poitiers any access to Henri’s deathbed, ignoring her husband’s final pleas for his lover. After his death, she banished Poitiers and her friends from Paris.

She also ordered the surrender of Poitiers’s crown jewels and her fine castle, the Château de Chenonceau. Even years later, Catherine made her real opinion heard on Poitiers in a letter to one of her children which read, “Never has a woman who loved her husband liked his whore.”

34. Corporal Punishment at the French Court

When Catherine’s youngest daughter, Marguerite, was found to be having an affair with Henry of Guise, Catherine and her son Charles IX allegedly had the princess pulled from her bed, her nightclothes ripped, and hair torn from her head as punishment. Yowch.

35. Mother’s Mercy (Is Non-Existent)

The complicated relationship between Catherine de Medici and Marguerite was made harder by Marguerite’s tendency to cheat on her husband. In October 1586, on Catherine’s orders, Marguerite’s husband imprisoned his wife and executed her lover although not right in front of Marguerite, as Catherine had wanted.

Small victories, I guess…

36. The Pen Is Mightier Than the Sword

Oh hey, do you like well-known macho writer Norman Mailer? If so, you might not want to read this horrific fact. Mailer, who critic Jennifer Wright respectfully called “the worst,” once honest-to-God stabbed his wife Adele while he was drunk at a raucous party. But that’s not even the worst part. Did I mention that it was with a rusty penknife? Did I mention that he did it twice?

37. The Second Cut Is the Deepest

After hitting Adele in the back, Mailer then punctured her chest and just narrowly missed her heart. Apparently, when people tried to be half-decent and attend to her, he only spat out some utterly cruel words: “Don’t help her. Let the witch die.” Though Adele never pressed charges for the sake of her children, she did divorce Mailer two years later. Darn right she did.

38. Fall From Grace

You could fill a list with episodes from F. Scott and Zelda’s Fitzgerald’s chaotic relationship. Few got more explosive than the aftermath of Scott having some private time with a sex worker, just to dispel rumors of an affair with Ernest Hemingway. Unfortunately for F. Scott, his wife Zelda discovered the condoms and a bitter estrangement ensued. It perhaps ended with Zelda throwing herself down a flight of marble stairs as Scott was enthralled in conversation with dancer Isadora Duncan.

39. Don’t Call Me, I’ll Call You

20th-century writer Edith Wharton gained fame for her novels about the desperate affairs hidden underneath buttoned-up New York society, but few readers know that her own bedroom life rivalled her tragic fiction. Stuck in a dull marriage, Wharton started a steamy affair with the journalist Morton Fullerton for a year—until it came to a bitter end.

40. Silent Treatment

One day, Fullerton just full-on ghosted her. He pretty much stopped replying to her letters, leading her to send the early-20th-century equivalent of that embarrassing 2 AM text we all wish we had never sent. “Dear,” she wrote, “Will you not tell me the meaning of this silence?” He…never did. Oof, we’ve all been there, Edith. Chin up.

41. Always Read the Terms & Conditions

As Albert Einstein’s marriage to his first wife fell apart, he tried to lend some order to their domestic life. This came in the form of “Conditions,” which laid out a code of conduct. Among other things, he told her to ensure “that I will receive my three meals regularly in my room” and “that my bedroom and study are kept neat, and especially that my desk is left for my use only.”

Basically, he told her to “renounce all personal relations with me insofar as they are not completely necessary for social reasons” and to “not expect any intimacy from me,” although that last part about intimacy goes without saying at that point.

42. Aunt Big Bucks

Charles Brandon was a close friend of Henry VIII, and like his buddy, Brandon had some intense marital mishaps of his own. In around 1506, Brandon started sleeping with a lady named Anne Browne. She got pregnant, leading Brandon to promptly dump her and marry her rich widowed aunt Margaret Neville. Oh, but it gets worse.

43. Whiplash

Brandon ruthlessly manipulated Aunt Margaret. He sold her lands for cash, then divorced her on the grounds of “consanguinity.” Yup, he divorced her by bringing up the fact that he used to be in a relationship with his wife’s niece Anne Browne. Oh, and after he ruined Aunt Margaret’s life, he hopped back into bed with his original girlfriend Anne. What a gentleman.

44. I Do, I Guess?

It would be an understatement to say that Napoleon Bonaparte’s second marriage started unhappily. He had divorced his beloved but barren wife Josephine and wed this new bride just to get an heir. Right on his wedding day to Marie-Louise, he is said to have bluntly told the blushing bride, “I am marrying a womb.” If that doesn’t inspire you to write your vows, I don’t know what will.

45. Neighborhood BBQs Must Be Awkward

In Victorian Britain, divorce remained a luxury for the rich. Men of lesser means had to reach backwards, far backwards, to escape marriage. In one case, a man used an old English legal precedent to sell off his wife to the highest bidder (he tried selling off the kids too, but the buyer said no thanks). By all accounts, the wife left happily into the arms of her buyer: their next-door neighbor.

46. Watch Out Boys, She’ll Chew You Up

Duchess. Bigamist. Hustler. Criminal. Say what you want about her, Lady Elizabeth Chudleigh definitely made an impression. This scandalous courtier was the maneater of the 1770s. She secretly married Augustus Hervey, then after that fizzled out, she tied the knot with another gentleman…without getting a divorce from her first husband.

Yup, our girl was married to two high society gents at the same time. It all fell apart when she was convicted of bigamy, but hey, don’t hate the player, hate the game.

47. Where’s Maury When You Need Him?

Catherine the Great and her husband Peter didn’t have the best marriage. He was notoriously childish and would rather play with his toys than go to bed with his wife. Not only did Catherine have three kids who were definitely not Peter’s, but she and her lover also hatched an ingenious plot to kick Peter off the throne and get Catherine declared the ruler of Russia.

Even worse, soon after Catherine took power, one of her co-conspirators killed Peter in cold blood. Now that’s a dramatic marriage.

48. Mystery at Mayerling

In 1889, the 17-year-old Baroness Marie (Mary) Alexandrine von Vetsera was found apparently shot to death alongside her lover, the married Prince Rudolf of Austria, at their Mayerling country hunting lodge. His shooting partner had gotten worried. He broke down the door with an axe, only to find a horrific sight: Rudolf slumped at the bed with blood at his mouth.

His mistress Marie was lying on the bed, also stone-cold dead. It was an apparent murder-suicide; but to this day, the sequence and chain of events leading up to their deaths remain ambiguous. Although some assumed the prince killed his lover, recently discovered letters from the Baroness to her mother indicate that she was planning to die alongside the prince “out of love.”

49. Unlucky in Love

Silent film heartthrob Rudolph Valentino impulsively married his first wife, actress Jean Acker, in 1919, two months after they met. While most girls could only dream of landing the famous Hollywood heartthrob, Acker wasn’t like most girls…

50. Playing Hard to Get

On Valentino and Acker’s wedding night, the bride locked Valentino out of their hotel room and coldly ended the relationship then and there. What led her to such a cruel decision? Well, it turns out that Acker wasn’t even interested in men. She got back together with an ex-girlfriend named Grace Darmond soon after she left Valentino. Guys always want what they can’t have…

51. Not-So-Smooth Sailing

Valentino’s second marriage was somehow even rockier than the first. His second bride Natascha Rambova was not popular with a number of Valentino’s friends and the marriage disintegrated to the point where Rambova was eventually banned from his film sets. That bad blood didn’t end when he died. In his will, Valentino left Rambova an utterly cruel tribute.

He bequeathed her one single dollar bill. Ouch.

52. Confessions of a Middle-Aged Drama Queen

Ada Lovelace was the daughter of the notorious poet/rampant womanizer Lord Byron, and she inherited a few traits from her philandering father, not all of them good. In addition to a sharp mind—Lovelace is often considered the first computer programmer—and a huge gambling problem, Byron’s daughter also sure knew how to kick off a bitter breakup.

On her deathbed, she made a mysterious confession. Her husband stormed out of the room and never came back. To this day, we still don’t know what she said.

53. Third Time’s the Charm?

King Henry VIII was not a man to waste time. Within 24 hours of executing his second wife, Anne Boleyn, he was already engaged to his mistress, Jane Seymour. Seymour eventually gave him his long-desired son, Edward VI, but she died two weeks after giving birth. She was the only of Henry’s six wives to be buried with him, and Henry considered her his first “true wife.”

54. Renaissance Tinder

After Seymour’s death from complications of after giving birth to Edward VI, Henry VIII began the search for his next wife. In order to choose, Henry was sent paintings of possible partners. He chose Anne of Cleves over her sister Amalia, but was unhappy with his choice when he finally saw her in person.

He called her a “fat, Flanders mare,” and had the marriage annulled after just six months. At least she kept her head!

55. Off With Her Head!

Sixteen days after annulling his marriage to Anne of Cleves, Henry VIII (now 49) married the 19-year-old Catherine Howard, who had been Anne of Cleves’ lady-in-waiting. Less than a year into their marriage, rumors of her infidelity began, and after gathering evidence of her promiscuity, Henry had her executed in 1542.

Wikipedia

56. Weren’t Six Wives Enough?

Henry VIII had at least ten mistresses over the course of his six marriages, beginning approximately a year after his marriage to Catherine of Aragon. It’s a truly fascinating phenomenon because while a little bit of extramarital activity was not exactly new behavior for a monarch, such brazen and unapologetic philandering absolutely was.

And yet, when others attempted to corral Henry’s increasingly wild libido, he simply found a way to brush them off. Just think of it: the man changed the entire country’s relationship with the state religion—just to accommodate his lust. That’d be like an American president altering the constitution in order to justify his execution of the First Lady. Crazy stuff.

57. Quite the Social Life

Long before the Kardashians became famous for being famous, that honor went to Zsa Zsa Gabor. While she was a noted actress in her prime, Gabor’s more lasting fame came from her scandalous socialite activities in the most elite circles of Old Hollywood. During her life, Gabor was married to nine different men, and seven of these marriages ended in divorce, while another was annulled.

But hey, maybe Zsa Zsa was just an utterly hopeless romantic?

58. Born Comedian

Gabor wasn’t just a pretty face. She was known for her razor-sharp wit, a penchant for one-liners, and self-deprecating humor. On one occasion, when talking about her notorious love life, she quipped, “A girl must marry for love and keep on marrying until she finds it.” In reference to her many divorces, she later joked, “I am a marvelous housekeeper. Every time I leave a man, I keep his house!”

Something tells us this woman would have been legendary on Twitter.

59. Keeping It Symmetrical

One of Gabor’s many husbands was Oscar-winning British actor and singer-songwriter George Sanders. Like many of Gabor’s relationships, their love was incredibly passionate but also incredibly volatile: they married on April 2nd, 1949 and divorced exactly five years later to the day, on April 2nd, 1954. Really, it’d be poetic if it wasn’t so sad.

60. Sisters Share

Maybe Sanders never quite got over Zsa Zsa, because in 1970 he married her older sister Magda after a whirlwind romance. Unfortunately, this union was just as ill-fated as his other foray into the Gabor family: they divorced after a mere 32 days, and the split even quickly drove Sanders into an alcoholic bender.

61. Biblical Bad Boy

Herod the Great was king of Judea. Modern readers might recognize him as the King who wanted to kill Baby Jesus in the Gospel of Matthew. He was also accused of killing his brother-in-law, whom he had named a High Priest at the insistence of his wife, Mariamne. Suffice it to say, Herod had a bad reputation.

62. That’s Why He Called Her Honey

When you have a bad reputation—as Herod did—people are likely to say outrageous things about you. Things like, “Herod believed his wife Mariamne had committed adultery so he had her executed. But he still loved her, so he had her body preserved in honey and had sex with her for another seven years. Then he married a woman named Mariamne II.”

63. Meeting His Love

While it’s true that Writer F. Scott Fitzgerald and his wife Zelda had a pretty tricky relationship, Zelda really was his first and one true love. He met her while stationed in Camp Sheridan, Alabama during the war (she was the daughter of an Alabama Supreme Court Judge). They fell in love and he proposed, but she broke off the engagement when the war ended, convinced that he wouldn’t be able to properly support her working as a writer.

64. A Match Made in Heaven?

So yes, Zelda Fitzgerald’s marriage to F. Scott was the textbook definition of toxic relationship. They were both alcoholics, they were mutually unfaithful, she accused him of having a gay relationship with Ernest Hemingway, and she had multiple nervous breakdowns, eventually being diagnosed with schizophrenia. All of this only got worse as the years wore on, and they were estranged at the time of his death.

65. American Woman

Perhaps the biggest royal scandal of the 20th century came when the sitting King of England abdicated his throne. King Edward VIII took the throne in 1936, following the death of his father. There was just one problem: Edward was in love with Wallis Simpson, a commoner from Baltimore who was already on her second marriage. This was a major no-no among the British aristocracy.

It also conflicted with Edward’s role as head of the Church of England, which disapproved divorce—sorry, did they forget what they had been created for? Either way, as his entire cabinet said they would resign if he proposed, Edward’s insistence on marrying Wallis—as soon as her divorce finalized, of course—threatened to launch Great Britain into a constitutional crisis.

66. Two Strikes, You’re Out

Few Hollywood “love stories” match the drama of Elizabeth Taylor and Richard Burton. Married to other people when they hooked up while shooting Cleopatra, the couple themselves would marry and divorce each other twice. They first got hitched in 1964, but divorced in 1974 after Burton had an affair with a young co-star.

However, the two realized they were still in love after a meeting about their financial affairs, and married again 1975… before they divorced for the second (and last) time in 1976 due to Burton’s wandering eye (again).

67. King Ludwig of Bavaria: The Mad Dreamer

Though he was a pretty ineffective ruler, King Ludwig II of Bavaria’s popularity never wavered. He was broodingly handsome and frequently rode the countryside in disguise, giving gifts and large sums of money to the kindlier and more hospitable farmers he met along the way. To the Bavarians, Ludwig was the ideal romantic hero.

To those who really knew him, Ludwig’s true nature was much darker.

Ludwig of Bavaria factsiCollector

68. Breakups Are Hard

In 1867, Ludwig became engaged to his cousin, Duchess Sophia of Bavaria. Sophia was the sister of his beloved friend, Elizabeth. After several postponements, the engagement was finally broken off in October of that year. While no reason was ever announced, Ludwig claimed in a letter to Sophia, “your cruel father has torn us apart!”

69. Below the Surface

Although Tom Cruise and Nicole Kidman called their divorce as an “amicable separation,” their settlement was less than friendly. Cruise listed their separation date as December 2000—just shy of their tenth anniversary—while Kidman contended she was informed of their divorce two months later, in February 2001. This little difference actually was a very big deal. 

70. Racing Against the Clock

Under California law, a marriage is considered “long-term” at ten years, at which point Cruise would have to support his ex until she remarried. Cruise reportedly caved to Nicole’s demands after she threatened to use DNA samples to prove she had suffered a miscarriage just weeks after Cruise announced their separation. Yeah, it doesn’t sound that amicable to me.

71. The E-Meters Told Me So

There was also speculation that Scientology was to blame for the divorce, but very little was known about the split’s awful details until former Scientologists revealed that Cruise and the Church of Scientology actually had Kidman’s phone tapped during their marriage. Cruise and Kidman’s two children also reportedly refuse to speak to their mother since the divorce, and have called her a “suppressive person.”

72. Eat Your Heart out, Dad!

The future King Peter I of Portugal was deeply in love with Inês de Castro, to the point where he neglected his own wife and endangered the international alliance. Infuriated, Peter’s father sent three men to decapitate Inês. In revenge, the heartbroken Peter found two of her killers and had their hearts viciously ripped from their bodies. But he was just getting started. 

He then exhumed his wife’s body, placed her on a throne, and forced his entire kingdom to bow before her corpse and kiss her hand. Creepy, but touching!

73. The Definition of On-Again Off-Again

Divorce was only a punctuation mark in the long, complicated story of Marilyn Monroe and Joe DiMaggio’s relationship. They had been married for only nine months when Monroe announced that she was divorcing DiMaggio on the grounds of “mental cruelty” and his possessive behavior. DiMaggio didn’t take it well; he would show up to her house at random to see if she was with new men.

He also enlisted his friend, none other than the also recently divorced Frank Sinatra, to have Monroe’s phone bugged (the “possessive” part is ringing true). But he didn’t stop there. 

74. Endless, Problematic Love

Even when his harassment abated, DiMaggio never got over Monroe—when she overdosed in 1962, he took charge of the funeral plans and sent flowers to her grave twice a week, every week, until he himself died in 1999. DiMaggio’s last words were reportedly, “I’ll finally get to see Marilyn.” Like sure, that’s romantic, but does that make up for the other stuff? 

75. Get In, Get Out, Stay Safe

When Katie Holmes divorced Tom Cruise after five years of marriage, she had reason to fear for her life. The Church of Scientology, to which Cruise is devoted, is known for treating defectors with harassment, intimidation, and threats of bodily harm. Holmes immediately went into hiding when the news broke.

She was eventually granted full physical custody of their daughter, Suri, and the matter was resolved in 11 days. Fortunately, Holmes’s father, a lawyer, had convinced her to sign a prenuptial agreement before the wedding. Good call, Pops.

76. Rags to Riches

Nell Gwyn is a risque Cinderella story. As the most famous mistress of Charles II, she was born to abject poverty, yet somehow died in wealth and popularity as the icon of the English Restoration. These days, Gwyn is also remembered for her legendary insults, and her status as one of England’s first professional stage actresses.

77. It’s Not Size That Matters

In terms of appearance, Nelly had chestnut hair, hazel eyes, and a heart-shaped face. In contrast to the buxom bodies favored by Restoration beauty standards, however, Gwyn was petite, albeit “shapely.” What matters is that her future lover King Charles II had very few complaints about the beautiful, seductive woman…

78. A One-King Woman

Charles II took many mistresses, and some of them returned their king’s infidelity. For example, he once caught one of Nell’s rivals, Lady Castlemaine, in a “not good” position with the Duke of Marlborough. In contrast, Nell Gwyn was reported to be monogamous to King Charles II until his death, and thereafter as well.

79. Salary Negotiations Are Tough in Any Century

Gwyn’s greed almost got in the way of her meeting Charles II. By late 1667, the Duke of Buckingham was seeking a mistress—but not for himself. The lord intended to remove the politically inconvenient Barbara Palmer from the King’s favor by arranging a rival in the royal bed. Nell’s talents put her in the running, but she made the mistake of asking too much money.

Her demands to be paid £500 a year were just too steep, so Buckingham went with Moll Davis—who was also Gwyn’s rival in acting. Ooh, I smell a scandal.

80. Love Bites Back

Nell Gwyn passed away when she was in her 30s. It was believed she died from apoplexy caused from late-stage syphilis. That’s quite the parting gift.

81. His Filmography, Her Bank Account

Mel Gibson and his wife Robyn were married for almost three decades and had seven kids together. As Mel’s mental health destabilized, evidenced by his drunken anti-Semitic rants, Robyn filed for divorce in 2007 (can’t blame ya there, Robyn). As part of their settlement, Robyn received more than $425 million. On top of that sweet plum, she also gets half of the residuals on all the projects that he worked on during their marriage.

82. Putting the “Ew” in “Hugo”

The French author Victor Hugo was a notorious philanderer—but he was also a dad trying his best. These two roles came together when his son’s partner, the actress Alice Ozy, began seeing other men. In response, Hugo slept with Alice himself, thinking that the embarrassing affair would “avenge” and cheer up his son. The boy was shockingly ungrateful towards Hugo’s efforts.

83. Musical Disharmony 

Paul McCartney didn’t have a prenup when he married Heather Mills. As a result, the former Beatle had to pay his wife $48.6 million in the divorce. The singer later called the marriage one of his worst decisions ever.

84. Wandering Eyes Settle Down

Acting legend Humphrey Bogart’s marriage to Mayo Methot was always fraught with drama; the tabloids had even dubbed them “the Battling Bogarts” (Methot once stabbed Bogart in the shoulder, but Warner Brothers suppressed the scandal). But when Methot caught word of her husband’s on-set affair with a woman young enough to be their daughter—the 19-year-old Lauren Bacall—she came to the set of The Big Sleep to keep an eye on them.

Not liking what she saw, Methot apparently sent Bogart packing (although some say he initiated the divorce). Soon after, Bogart wed Bacall, and the pair remained together (in an open marriage) until his death in 1957.

85. A Genetic Lack of Chill

Margaret Tudor has been frequently overshadowed by her infamous older brother Henry VIII, but as a thrice-married, husband-deposing, serial divorcee and regent of Scotland in her own right, Margaret pursued enough scandal to hold her own against her brother. Unfortunately, she also had a serious problem with self-control.

While this character flaw was bad news for her political career, it certainly makes for a new, salacious, and lesser-told story in the Tudor canon.

85. My Girl for Some Peace and Quiet

Before she was even 6 years old, Margaret was betrothed to the 22-year-old King James IV of Scotland. Her hand in marriage would seal England and Scotland’s sweetly named “Treat of Perpetual Peace,” in which King James agreed to stop sending pesky usurpers (and violent raids) to Henry VII’s doorstep. In exchange, Henry would give him his eldest daughter. Name a better deal?

86. The Rebound Regent

Less than a year after her husband King James’ sudden death, Margaret eloped with Archibald Douglas, Earl of Angus. As per the terms of her husband’s will, the marriage effectively ended Margaret’s regency over her son.

87. Brother, Can You Spare a Room?

Margaret did not have a peaceful exit from the Regency. Pregnant with her second husband’s child, she accepted her brother King Henry VIII of England’s help to flee from the country for the safety of her own life under the Duke of Albany’s regime.

88. Well, That Was Fast

Margaret’s marriage to Archibald Douglass produced one living daughter, Lady Margaret Douglas. Their bliss was not to last. After a year away in England, Margaret returned to Scotland to an upsetting sight: Douglas was living with another woman on Margaret’s dime.

89. Don’t Give Him Ideas

Upon discovering her second husband’s adultery, Margaret immediately sought to divorce him in 1518. Her brother, Henry VIII, was aghast that his big sister would treat the sacrament of marriage so lightly. Centuries later, Henry’s offense remains the source of riotous laughter for many historians.

90. A Coup d’Estranged Wife

By 1521, Margaret Tudor was both romantically and politically alienated by Angus, who was living with another woman and withholding control of her lands as well as a place in her son’s government. Luckily for Margaret, she was able to successfully campaign for her once-rival the Duke of Albany to return and seize the government from her own husband’s faction.

91. Take My Wife, Please

In November 1521, Margaret successfully waged a coup against her husband, Angus Douglas. The rebound beau was relieved of all his government titles. Douglas could only watch as his wife marched victoriously into Edinburgh, side-by-side with their once mutual enemy, the Duke of Albany.

92. Marriage So Bad, You Make a Queenly Run for It

Margaret was officially divorced from Archibald Douglas in March 1527. Just one year later, she married Henry Stuart, who turned out to be even more adulterous and wasteful than her second husband. 10 years later, Margaret was petitioning for her second divorce. How miserable was she? Several times, Margaret tried to escape across the Scottish border back to her home country.

She was carried back to Edinburgh each time.

93. Triple Threat

Virginia Oldoini—known better to history as the Countess of Castiglione—was born to a family of minor nobles in Tuscany on 22 March 1837. From these relatively humble beginnings, she would rise to become a legendary model, spy, and mistress to none-other than the Emperor of France, Napoleon III.

94. Broken Heart Queens Club

By 1860, Oldoini’s affair with Napoleon III had soured, and she had completely lost favor at his court. The reasons for her sudden fall from grace remain a private mystery.

95. Putting the “Snap” in Snapchat

The Countess of Castiglione’s fashion shoots often doubled as warning shots to her enemies. When her estranged husband tried to claim custody of their son, she sent him a photo herself in loose hair…and with a knife barely concealed in her hand. Naturally, the photo was titled “La Vengeance.” Subtle!

Countess Castiglione FactsShutterstock

96. Why Scale the Steps of Love When You Can Fly?

Louis XV owned one of the first modern elevators. In 1743, he came into possession of “The Flying Chair”—a device where he would sit in a throne and be pulled by several men into the next story of Versailles. Naturally, he installed his elevator as a discreet means to visit his mistress without having to take the stairs.

97. A King Waits for No One

At first, Louis XV and his wife Queen Marie Leszczyńska had a loving relationship. The king mostly took lovers as “substitutes” in his bed during Marie’s many pregnancies. The couple’s polite arrangement changed in 1738 when the Queen dangerously miscarried. Her doctors warned her against sex until she was fully recovered. Insulted—because he’s really the one suffering here, right?—Louis could not forgive Marie’s (medically prescribed) rejection and he never came to her bed again.

98. Self-Fulfilling Prophecy?

King Louis XV’s chief mistress was a woman named Madame de Pompadour. When Pompadour was a little girl, she was taken to a fortune teller by her mother. The fortune-teller allegedly foretold that Pompadour “would one day reign over the heart of a king.” Pompadour would later be groomed to fulfill that prophecy by becoming the mistress of King Louis XV.

She also gained a new nickname which would stay with her for the rest of her life: reinette. In French, this word means “little queen,” quite an ambitious name for such a little girl!

99. Speaking of Cup Size…

One long-standing legend is that the shape of the French champagne glass, also known as the coupe, was originally modeled after the size and shape of Pompadour’s breast. It remains unconfirmed whether this is true, but the story has endured across history.

100. From Lover to Friend

While on the outside, Louis XV and had a happy healthy relationship with his chief mistress, Madame de Pompadour, modern historians now know that the couple hid a dark secret behind bedroom doors. From 1750 onwards, Pompadour ceased being a sexual partner to Louis XV. They no longer actually made love. This was attributed to her very poor health.

Over the years as Louis XV’s mistress, she suffered three miscarriages, and also “suffered the after-effects of whooping cough, recurring colds, and bronchitis, spitting blood, … as well as an unconfirmed case of leucorrhoea.” Yikes.

101. For Sale; Love Nest, Never Used

In 1762, Madame de Pompadour convinced Louis to construct the Petit Trianon, a luxurious mini château within Versailles that would serve as their love nest. Unfortunately, Pompadour passed away before construction could be finished. But don’t worry, it didn’t go to waste: the Petit Trianon went on to serve as home base to Pompadour’s successor in the royal bed, new maitresse-en-titre, Madame du Barry.

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