Nobody likes a breakup. Whether we’re the dumpee or the dumper, a romantic split means hours of crying, days of despondence, and entire seasons of Vanderpump Rules (No? Just me?). We can lose friends, pets, and that really nice slow cooker our ex’s mom bought us for Christmas. In a word: It sucks. But does your worst breakup suck as much as these historically horrific splits? I do not think so.
1. An Intimate Gift
Lord George Byron was the bad boy poet and notorious lothario of the 19th century, so he obviously had no qualms about taking up with the very beautiful (and super married) writer Lady Caroline Lamb. Living up to his rake persona, the good Lord Byron also had no problem loving and leaving her—but Lamb’s response to their split was utterly disturbing.
When things started going south, Lamb cut off a chunk of her hair “down there” and sent it to the poet. Yep, that’ll make him miss you, Caroline. Except that wasn’t even the worst part.
2. Forging Ahead
Long after Byron and Lamb were done for good, the embittered exes just couldn’t resist screwing each other over. Being dramatic artist types, they did this in utterly insane fashion. Lamb apparently wanted a particular painting of Byron to remember him by, but she knew he’d never give it to her. What’s a lovelorn girl to do? The answer to that question is apparently: forgery.
Lamb forged a bang-on accurate letter of permission from Byron, brought it to his publisher, and took the trinket for herself. And this story isn’t even over yet…
3. Lost the Breakup by a Hair
Once Byron found out about Lamb’s Grand Theft Artwork, he tried to get the painting back from her for months. Makes sense, I wouldn’t want a creepy ex staring longingly into an approximation of my face, either. Then, to Byron's surprise, Lamb finally agreed to return it—but she had one creepy condition. She wanted a lock of his hair in exchange for the painting. This is when Byron took “sick burn” to the next level.
Reader, he sent over a lock of his new girlfriend’s hair. I want to be mad, but all I feel is respect.
4. Words to Live by
Caroline Lamb was the one who famously called Byron “mad, bad, and dangerous to know". Yeah, I think I see why…
5. Love/Hate Relationship
Emperor Nero of Rome wasn’t exactly known for his rational decisions or his even temper as a ruler. From ending his own mother to playing his lute as the city burned, Nero was totally off his rocker, and that's putting it lightly. Surprise surprise, he was no better in the love department. Exhibit A: Nero ended his first wife just so he could marry his new crush, Poppaea Sabina.
Exhibit B: He later ended Poppaea by punting her in her pregnant stomach. Her demise may have been an accident, or he may have been intending to do it—but at a certain point, does it really matter?
6. Nero’s Drag Race
After his sweetum Poppaea’s accidental demise/liquidation, Nero really gave new meaning to the phrase “breakup blues". Instead of simply getting over his dearly departed wife, Nero did the sensible thing instead. He promptly hired a 14-year-old boy he dubbed “Sabina” to dress up as a woman and act as an Empress of Rome. Whatever floats your boat, Nero.
7. That Was Way Harsh, Henry
Ugh, breaking up with a King of England is the worst. King Henry II’s wife Eleanor of Aquitaine was one ball-busting historical lady, and she didn’t much like her royal husband. By 1173, their marriage was on the rocks—so much so that Eleanor helped her sons plan a revolt against their own father. Sadly, the family plan took a horrific turn.
Henry won the revolt, punished his sons, and then imprisoned Eleanor for over a decade. The king kept a close, not-so loving eye on her until the day he lost his life in 1189.
8. 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.
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.
9. 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.
10. Voodoo Woman
For some mysterious reason that I couldn’t possibly explain, Kokoschka just wasn’t, er, satisfied with this new Alma. No matter how much he painted the doll and posed her in sensual positions, the magic just wasn’t there anymore. So, in a fit of rage, he officially broke off the relationship by destroying the doll in the middle of a party. And people say art therapy doesn’t work.
11. Sixth Time’s the Charm
King Henry VIII. The Mack Daddy of Dumpers. The Sultan of Splits. The Honcho of Heartbreak—you get the point. But seriously, the notorious King of England had no less than six wives with a pretty miserable spousal survival rate among them. He also had a type: All of his wives were related, and could trace their ancestry back to Edward I of England.
12. I Did It All for the Nookie
King Henry’s first breakup came when, frustrated at his lack of a male heir, he decided to divorce his wife Catherine of Aragon and trade her in for the younger, bewitching Anne Boleyn. But you can’t say the man wasn’t committed. To do the deed, he had to trigger the whole darn English Reformation and basically invent a new religion to get that sweet, sweet divorce. Weird flex King Henry, but OK.
13. 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 spiked his wife Adele while he was inebriated 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?
14. 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 perish". Though Adele never pressed charges for the sake of her children, she did divorce Mailer two years later. Darn right she did.
15. Love Means Never Having to Say You’re Sorry
But wait, it gets creepier. After, you know, attacking his own wife, Mailer didn’t really lose friends. In fact, many of his intellectual buddies defended his actions as an extension of his “art". James Baldwin defined the attack as an attempt to free himself from a “spiritual penal institution,” while critic Lionel Trilling called it a “Dostoyevskian ploy".
There’s rallying around a pal after a pretty bad breakup, and then there’s this. Yikes guys, yikes.
16. Art Imitates Life
Edvard Munch’s painting The Scream is one of the most visceral representations of existential dread, but believe it or not, it’s got nothing on Munch’s tormented personal life. In 1898, Munch started a steamy affair with an artist’s model named Tulla Larsen. Oops, did I say “steamy affair?” I actually meant “agonizing, life-ruining ordeal".
17. Pointing the Finger
Tulla Larsen was strong-willed and opinionated, while Munch was…a whiny little wimp, if I’m being honest. Larsen kept pressuring him into marriage, and Munch kept avoiding the situation big-time. Tensions rose—until the horrific day it all unraveled. During a bedroom altercation, Munch ended up cutting off part of his finger.
Edvard Munch, CC BY 4.0, Wikimedia Commons
18. Persecution Complex
Never one to pass up an opportunity for self-pity, this violent event affected Munch for the rest of his life, and he made sure that everybody knew it. Munch once even painted himself as Christ nailed to the cross, which is not a good enough reason to compare yourself to Jesus. The worst part? After all that drama, Larsen said “boy, bye” shortly after, marrying another man.
19. Burn After Reading
Surprise! “Honest Abe” is a dirty liar. Sort of. When he was a young man, Abraham Lincoln’s friend Elizabeth Owens kept trying to set him up with her sister Mary, despite the fact they had never met and lived in different states. One day, just to get Elizabeth off his back, Lincoln joked that he’d wed Marry if she moved to Illinois. This was a huge mistake.
20. Baberaham Lincoln
Unfortunately for Abe, Mary was apparently just a tad thirsty. She immediately took his offer seriously, forcing the lanky lad into a very awkward situation. Abe had to send a series of frantic letters explaining that he thought it was more a “lol, jk” kind of thing and trying to convince Mary that she’d be so much better off without him.
21. Beauty and the Beast
In the 17th century, there was a no bachelorette more eligible than Hortense Mancini, a renowned court hottie with a behind-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.
22. 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.
23. The Runaway Duchess
In 1668, Hortense Mancini actually 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".
24. Together Forever
Sadly, Armand-Charles had the horrific last laugh when it came to his ex Hortense. After she perished, 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 body and paraded it around France for months.
25. Absence Makes the Heart Grow Bolder
Screen siren Ava Gardner and her hubby Mickey Rooney had a notoriously troubled marriage, but the final straw was a real doozy. An ailing Gardner came back from a long hospital stay looking forward to a night in her own bed. Instead, she found out that Rooney had been using their away time to deal her a heartbreaking betrayal. He was seducing multiple women—in the couple's marital bed.
26. Daddy Issues
Napoleon Bonaparte famously adored his wife Josephine, but few people remember the dark end of their love affair. Tragically, Josephine was barren, and Bonaparte really wanted to make some little(r) Napoleons. So he made a hard choice: He divorced Josephine and took up with Marie-Louise of Austria. But if you think love is gone, worry not. Napoleon reportedly told his blushing bride straight off, “It is a womb that I am marrying". Aw.
27. Poetic Injustice
The poet Percy Bysshe Shelley might have been a Romantic genius, but the dude still sucked at love. Oh, it’s true that he and Mary Shelley had the ultra-dark goth teen romance to end all goth teen romances, complete with make out sessions on her mother’s grave, but that version of the story omits one crucial detail. When he met Mary, Percy was already married to Harriet Westbrook—and it did not end well.
28. A Watery Grave
Faced with fidelity to his wife or getting it on with a hot new sidepiece, Shelley did the courageous thing and full-tilt abandoned Harriet, running away with Mary to Switzerland. Harriet, never in good mental health and now utterly despondent, drowned herself soon after. Sadly, it gets worse: Harriet was very pregnant with Shelley’s child at the time.
29. Wife Swap
Ernest Hemingway was super in love with his first wife Hadley Richardson—that is, until her good friend Pauline Pfeiffer came along. At that point, Hemingway had no issues dumping Hadley and marrying Pauline faster than you can say “best friends for never".
30. 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.
Wikimedia Commons
31. A Royal Affair
Hortense Mancini was legendarily irresistible to both men and women. In one seriously incredible story, she took up with the King of England’s illegitimate daughter Anne Lennard. There was just one problem: Anne was married, and her husband wasn’t happy about the tryst. Which is right about when it all came to an amazingly bizarre climax.
32. Touché
For some reason—ahem, foreplay—Anne and Hortense kicked off a public fencing match with each other while wearing only their underclothes. Anne’s husband found out and took his wife away to the country where she couldn’t be tempted by (I can only assume) a better lover. While Hortense got over it immediately, it's safe to say that Anne…did not.
Reportedly, Anne stayed in her bed at all hours of the day, demanding to kiss a miniature portrait of her beloved Hortense.
Jacob Ferdinand Voet, Wikimedia Commons
33. Ring, Ring, the Witch Is Gone
When King Henry VIII and Anne Boleyn heard the news that his first wife Catherine of Aragon had finally perished, it’s said that they both wore bright yellow in celebration.
34. Going out Like a Queen
Sadly, as we now know, things went south fast with Henry and 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 end 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.
The Other Boleyn Girl (2008), Focus Features
35. 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.
36. Breakup on the High Seas
Anne Bonny and Calico Jack roamed the seven seas as fearsome pirate lovers, but eventually their luck—and love—ran out. When authorities caught their ship, Bonny stayed on deck to fight while Jack ran below. It was not a good look, and his (now ex) girlfriend did not mince words when she let him know it. After he was sentenced to hang, Bonny spat out, “Had you fought like a man, you need not have been hang'd like a dog". Drag him, Anne.
Black Sails (2014–2017), Starz!
37. Shots Fired
Old Hollywood is littered with scandalous breakups, but nothing quite matches heartthrob Gary Cooper’s violent split with Lupe Velez. Velez was the hot-headed jealous type, and Cooper’s multiple affairs gave her good reason to be. When it finally ended, Velez took the nuclear option and tried to shoot Cooper while he was boarding a train. Oh, we are never, ever, ever getting back together.
38. Big Cuck Energy
Victorian art critic John Ruskin sure knew a lot about painting and marble sculptures, but he was a total dum-dum in the bedroom. The night he married his nubile, 19-year-old wife Effie Gray, Ruskin was reportedly so disgusted at his first sight of an actual female body, he couldn’t bring himself to consummate the union. Like, ever.
After six unhappy years, Effie left Ruskin for his protégé John Everett Millais, who presumably spent no time blowing her mind. They did have 8 children together.
39. Family Matters
It’s tough when no one in your family likes your partner, but at least they never tried to liquidate 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.
40. Thank U, Next
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 cruellest words in history…
The Borgias (2011–2013), Showtime Networks
41. Too Close for Comfort
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: Forbidden relations 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 forbidden relations to this day.
The Borgias (2011–2013), Showtime Networks
42. There Were Three People in Her Marriage
You don’t get called “The She-Wolf of France” for nothing, and Queen Isabella was one heck of a predator. Her husband King Edward II was an inattentive lover, probably because he spent most of their date nights with his handsome favorite Piers Gaveston. Isabella dealt with the snub, but when Gaveston lost his life and Edward quickly found another favorite, she had enough.
43. Do I Have Your Attention Now?
Queen Isabella found herself her own lover, Roger Mortimer, and then took matters into her own hands. Before Edward could say “couples counselling,” Isabella and Mortimer deposed him. But it gets even darker. Some scholars think Isabella might have even liquidated her ex-husband, since he succumbed to a mysterious “fatal accident” while in her custody soon after. Either way, Isabella didn’t seem to mind a whole lot.
44. Breakup City
Elizabeth Taylor might have played the Queen of the Nile Cleopatra, but she was the Queen of the Breakup too. In 1959, the sultry brunette committed the ultimate betrayal. She broke up her best friend Debbie Reynolds’ seemingly idyllic marriage with Eddie Fisher. To give you a sense of the scandal, the Reynolds-Fisher-Taylor love triangle was like the 1950s version of when Brad Pitt left Jennifer Aniston for Angelina Jolie, or in other words, a total gong show.
45. Three Times a Lady
In a sweet twist, it looks like Fisher and Taylor were the real deal, with the couple staying together for the rest of their days. JK of course they didn't, this is Elizabeth Taylor we're talking about. Just three years after breaking up "America's Sweethearts," Taylor dumped Fisher for Richard Burton. She then married and divorced Burton not once, but twice—and she said she would have married him again if he hadn’t perished at 58.
46. The Flanders Mare
After only seeing a portrait of the mysterious Anne of Cleves, King Henry VIII decided to make her his bride. Yep, this was not a good idea. When Henry finally saw Anne in person, he thought this “Flanders Mare” was unthinkably ugly. The King immediately demanded an annulment—yet historians have suggested a more disturbing reason for his disgust.
Wikimedia Commons King Henry VIII
47. I Never Liked You Anyway
As it turns out, Henry met Anne of Cleves once before their official meeting—and their introduction couldn’t have gone worse. Henry disguised himself and snuck into her roadside accommodations to get a sneak peek of his bride. He then hugged and kissed her, expecting his soulmate to somehow understand who he was. Well, she didn’t.
Like most women faced with a random dude harassing them on the street, Anne treated the king coldly. As a result, some historians believe Henry decided to pre-emptively reject her before she could embarrass him in turn.
48. Pass the Pepper
Henry VIII’s second-last wife Catherine Howard apparently learned nothing from her predecessor Anne Boleyn, because Howard was even more reckless in the marriage. Though Anne’s charges of adultery were trumped up, the beautiful Howard probably was bonking Thomas Culpeper while married to the (to be fair) aging and obese King.
49. Divorced, Beheaded, Lied
Of course, this was far from King Henry’s first rodeo, and he gave his cheating wife a loud and clear “we’re over” message with a brutal decree. He sentenced her and her alleged lover to end. The night before her execution, Howard apparently spent hours practicing how to lay her neck on the chopping block to ensure the cleanest cut. Never let them see you cry, Catherine.
The Tudors (2007–2010), Showtime Networks
50. 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.
Sources: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 , 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28
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