Humans are imperfect, so of course their “love” proves impatient, unkind, envious, boasting, and self-seeking. It’s no excuse for awful behavior, but it does reflect how far we can fall from the standards we place on love. Here’s to the creepy couples, the killer couples, and the couples who didn’t let even death, or being an inanimate object, stop them from being together.
History’s Most Messed Up Love Stories Facts
42. Going Down the Family Tree
When Frances Folsom became First Lady to President Grover Cleveland, the scandal wasn’t just about their age difference (at 21 years old, Folsom is the youngest ever sitting First Lady to Cleveland’s 49 years). It’s also because her mom—Emma Folsom—was fully expecting a marriage proposal herself from the head of state.
Nevertheless, mother and daughter did not let a little thing like conflicting love interests get in the way of Frances’s nuptials.
41. Degrees of Separation
It recently came light that former New York mayor Rudy Giuliani married his own second-cousin, Regina Peruggi. The two had known each other since childhood and were married for 14 years until their divorce in 1982.
40. Hello From the Other Side
When Queen Victoria of England was widowed, she was utterly convinced that her beloved Albert didn’t truly leave her. For 30 years, Victoria would hold seances to get in touch with her consort’s spirit. The queen even wanted to publish the notes on their conversations, but her secretary had to put his foot down and stop that potential PR nightmare.
39. 8-Bit Love
There’s being “meant to be,” but there’s also “being programmed to kind of hate each other.” Meet Vincent and Emily—the robotic couple designed to be in a love-hate relationship. These androids can converse and argue via positive and negative signals. See, even robots go through rough patches.
38. Maybe A Third Would Have Been the Charm?
Two wives of Henry VIII were first cousins: Anne Boleyn and Catherine Howard. They were also the two who got executed.
37. That Is Too Close for Comfort
When it came to his dating pool, Henry VIII of England cast a short net. His first bride, Catherine of Aragon, served as godmother to the girl who would grow up become his sixth and last wife, Catherine Parr. As a baby, Parr was most likely named in honor of Henry’s first Catherine and queen.
36. You Call That a Knife?
When Edward IV of England married Elizabeth Woodville in secret, many had their own take on what really happened. And as with most gossip, the coolest takes had weapons. Some say Edward had attempted to take Elizabeth by force with a dagger; others say Elizabeth wielded the dagger and threatened Edward if he came closer.
Others see talk of weapons as dramatic flourish by envoys who thought to slander Edward for rejecting Bona of Savoy in order to elope with Elizabeth. It’s a twisted story no matter who cuts it.
35. Home State Before Heart
Some couples are hard to love, despite how much they might love each other. Alexander I of Serbia and Draga Mašin were such a couple. She was a widow 12 years his senior and a lady-in-waiting to his mother, whom Alexander banished for opposing her son’s match. Mašin’s influence was seen as undermining the country, amounting to rumors that her brother would be named heir.
At this, Serbia’s military had enough, stormed the palace, and killed the star-crossed lovers.
34. Stab Your Way to Spousal Privilege
A young Victorian Englishman named James Fauntleroy was once arrested and jailed for attempting to kill a romantic rival. In the cover of darkness, a young lady snuck into the jail and married Fauntleroy. That lady was none other than Mollie Downes, aka the only witness to the attack, aka the very girl that Fauntleroy had attacked the man over!
As his wife, Downes could not be legally forced to testify against her lover.
33. Cold Comfort
Not even the 19th century could escape the wrath of Florida Man. In 1881, a salesman from Utah took to the Sunshine State to marry a corpse. He had fallen head over heels in love with a woman who was dying of consumption. Unfortunately, she passed before their wedding day—but love stops for no one, and the man had her coffin taken to the church where they could be pronounced husband and wife before her burial.
32. You’ve Got Mail (and Murder)
When 47-year-old married father of two Thomas Montgomery pursued an online relationship with an 18-year-old known as “Jessi,” he thought he had a good thing going. Unfortunately, his wife found out and wrote to Jessi informing her of Montgomery’s real life. Jessi accordingly dumped her online beau for his 22-year-old colleague, Brian Barrett.
In the most extreme sense, Montgomery did not take it well, and killed Barrett with a sniper rifle. Yet that’s not the truly twisted part: when the police came to inform Jessi she might be next, they discovered no such “Jessi” in her home. There was only a middle-aged married mom (with a daughter named Jessi) who had been catfishing both Montgomery and Barrett the entire time.
The woman, Mary Shieler, technically committed no crime, but did not leave unscathed: her own husband and daughter deserted her, which makes about three different families swallowed up by this catfish.
31. Apology Bride
Monsieur Hamelin didn’t come to Madagascar in 1893 looking for love, but it found him. A wild beast found him too, promptly mauling his guide to death. This guide happened to be the brother of a local chief, who did not take kindly to losing a family member on account of this foreign horticulturist. The chief gave Hamelin a choice: greasy death by fire or marriage to the late brother’s widow.
Hamelin obviously chose the latter, and the chief chose to permanently close his kingdom off from European gawkers, perhaps wisely.
30. Deadly “Siblings”
Raymond Fernandez found a lot in common with Martha Beck. He liked to find lonely women through personal ads, woo them, and then rob them. She liked to help him do it. Together, they would pose as “brother and sister” and court vulnerable singles before taking their money. The con escalated into murder between 1947 and 1949 until they were arrested for causing at least 20 deaths.
Messed up is an understatement.
29. Revenge Selfie
Among the jilted mistresses of Chinese government officials, exposing corruption is all the rage. In one particularly high-profile case, a TV anchor named Ji Yingnan was swept into a high-rolling affair with Fan Yue, who began to lavish her with a thousand dollar a day allowance, apartments, and cars. But Fan was only a low-ranking official.
How did he afford all the stuff on a civil servant’s salary? His bosses and the government wondered the same thing after Ji bitterly spilled all their cozy selfies, and his sketchy spending habits, to the press.
28. Blood Love
Stop reading if you had tomato juice for lunch. In 2014, Aro Draven and Lia Benninghhoff met on a dating site. Soon, they were ready to share everything with each other—a relationship, a home, and each other’s blood. Every week, the star-crossed pair wine and dine on each other’s red stuff.
27. Self Love
In 1996, Dennis Rodman showed up in a wedding dress to the signing of his autobiography, As Bad As I Want to Be, and announced that he was marrying himself. But really, is this that messed up? After all, your most important relationship is with yourself.
26. No Longer Randy for Rand
When she was pushing 50, philosopher Ayn Rand started an affair with 20-something Nathaniel Blumenthal. He was a huge fan of her work, but he was also a married man. Nevertheless, Rand named him as her “intellectual heir” and even convinced him to change his surname to “Branden” so it contained her last name. However, when Branden moved on to another woman, Rand essentially blacklisted him from the Objectivist community.
And to top it all off, she publicly condemned him to impotence.
25. Bloody Valentine
While they were still together, Angelina Jolie and Billy Bob Thornton wore vials of each other’s blood around their necks. Like heart lockets, but with risk of infection!
24. Sixteen Candles
The Tudor dynasty was founded on the love affair between Owen Tudor and the widowed Queen of England, Catherine de Valois. Unfortunately, their end was quiet and grim; Catherine died after a few years of marriage and Owen was eventually executed during the War of the Roses. Yet even in death, Owen’s looks still drove the ladies mad.
While his head rotted on a spike, a random woman combed his hair, washed the blood from his handsome face, and set a 100 candles around the noggin’ that made ladies weep.
23. The Unamazed Maze
According to English folklore, Henry II of England sought to keep his affair with Rosamund Clifford on the DL from his wife, Eleanor of Aquitaine. Thus, he did the logical thing and hid Rosamund inside of an elaborate maze at Woodstock, Oxfordshire. Eventually, Eleanor got wise and penetrated the labyrinth. Acting just as practically as Henry, Eleanor presented her husband’s sidepiece with two options: stab yourself with this dagger or poison yourself with this bowl of toxins.
Rosamund chose the latter, less messy death. Of course, this story is almost definitely a fable, but it usefully reflects medieval ideas about love, commitment, and gardening.
22. Odd Couples
When H.G. Wells wasn’t spooking people with his writing, the science fiction novelist was busy having countless affairs in some really odd places. Wells’s repertoire was truly as inventive as his stories. His diverse portfolio of lovers includes figures like Soviet spy Moura Budberg and even birth control proponent Margaret Sanger!
21. Together 4Ever
Few can forget how Cleopatra of Egypt committed suicide rather than be captured by Roman forces. What’s less remembered is how her lover and consort—Mark Antony—went down right beside her. They had met as mere “frenemies” until she convinced the Roman general to join her cooler, sexier, side. And on that side, they died.
20. Achey-Breaky Heart
When his father sent assassins to behead his lover, Ines de Castro, it was Peter I of Portugal who tracked down the killers and ordered their hearts literally ripped from their bodies. After all, they had broken his own.
19. Last Choice Haircutters
Although it was a political marriage, the union between Joanna I of Castile and Philip “the Handsome” of Burgundy was one of passion, albeit lopsided passion. By all accounts, Philip was into Joanna, but just not enough to stay faithful. Unfortunately, Joanna was really into Philip. When Philip’s mistress had the misfortune of crossing paths with his wife, Joanna apparently snapped and hacked the other woman’s hair off with scissors.
Still unsatisfied with the ‘do, Jo then stabbed her in the face.
18. Say Boo to the Brew
To keep her husband faithful, it was rumored that Joanna I of Castile ordered her maids to mix love potions. Unfortunately for her, Philip listed “witchcraft” as one of his turn-offs.
17. Dumped on Your Wedding Night
Scotland partakes in an old but messy tradition called “The Blackening of the Bride.” During the ritual, bride and groom are pelted with rotten food. The logic goes that if the couple can make it through this mess, surely they can survive holy matrimony!
You might remember Elizabeth Siddal as the model for that iconic panting, Ophelia by John Everett Millais. Unfortunately, Siddal died over an overdose in 1862. Her husband, the painter Dante Gabriel Rossetti, buried a manuscript of poems inside her coffin as a final loving gesture. Years later, he decided he really wanted to publish those poems.
Accordingly, he had her body exhumed, and took back his gift to her.
15. 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 sex with a sex worker, just to dispel rumors of his having affair with Ernest Hemingway. 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.
14. Put This Track on Repeat
While F. Scott Fitzgerald was writing The Great Gatsby, his wife Zelda fell in love with a handsome French pilot named Edouard S. Jozan. She even asked Scott for a divorce, although they eventually stayed together. While this affair, understandably, made it hard for Scott to trust Zelda again, he loved for his wife to share this adulterous story to the Hemingways.
Eventually, the couple embellished the tale to point where they claimed Jozan killed himself from rejection (note: Jozan did not).
13. 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.
12. Tall Order of Love
In 2007, a woman named Erika LaBrie married the Eiffel Tower. She even took its name and now goes by “Erika Eiffel.”
11. Ready, Aim, I’m Seeing Someone Else!
Before she married the Eiffel tower, LaBrie had been in a long-term relationship with her archery bow. Naturally, it was named Lance.
10. Dream Girl Drawn to Life
At least two men in Asia have tied the knot with anime wives. In 2009, a Japanese man by the cyberpunk name of Sal9000 said “I do” to his virtual girlfriend from the dating simulation game Love Plus. Just months later in March 2010, a Korean anime fan had a more corporeal wedding with the girl of his dreams: a dakimakura body pillow with the name of Fate Testarossa…
Otherwise known as the heroine from the popular cartoon, Mahou Shoujo Lyrical Nanoha.
9. Uncle Big Bucks
Charles Brandon was a close friend of Henry VIII, and he had marital mishaps of his own. In around 1506, Brandon started sleeping with a lady named Anne Browne. She got pregnant, after which he promptly dumped her to marry her rich, widowed aunt Margaret Neville, Dame Mortimer. Eventually, he did make an “honest” woman of Browne and married her.
But only after he sold her Aunt Margaret’s lands for cash and then divorced Margaret on the grounds of consanguinity, based on his previous relationship Browne herself. What a gentleman.
8. I Do, I Guess?
Napoleon Bonaparte’s second marriage did not start happily. 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 bride, “I am marrying a womb.”
7. 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.
6. Hello, Dollface
When the artist Oskar Kokoschka came back from World War I, 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. 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 erotic positions.
Nevertheless, even this relationship went south, as 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?
5. When “Til Death Do Us Part” Isn’t Long Enough
Remember Joanna and Philip? Well, when Philip of Burgundy died, his wife Joanna refused to let him go. Literally. Refusing to part with her philandering husband, she viciously clung to the body. Even when her father and the government stepped in to finally bury Philip, their separation did not last long. Joanna ordered him exhumed, leapt at his coffin, and kissed his dead feet.
From that moment on, you couldn’t have Joanna if she couldn’t bring Philip. The coffin—thankfully closed most of the time—would accompany her to meals, travels, and even her bedside. Only years later did Philip return to the ground, albeit at a safe distance, i.e., buried right outside of her window. On the bright side, Joanna’s cheating husband was finally all hers!
4. 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 and broke down the door with an axe, only to find 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.”
The mystery doesn’t end there, however! In 1959, Mary’s remains were inspected. Shockingly, the examining doctor, Gerd Holler, found no bullet hole in her skull, but evidence pointed to death by violent blows to the head. Holler was now obsessed with the case. He went through the archives of the affair and found that only one bullet had ever been fired.
As a result, he theorized that Mary died in an accident (perhaps from an abortion), and that Rudolf subsequently shot himself in his grief. The full story, however, goes with them to their graves.
3. Friend Fiction
Simone de Beauvoir and Jean-Paul Sartre were the French philosophical power couple of the 20th century. They also had an open relationship, where de Beauvoir would take lovers and often “pass” them on to Sartre. One such woman was a young lady named Olga, who did not care to “advance” towards the “Jean-Paul Sartre” phase of this arrangement.
This rejection made Sartre obsessed with Olga, and therefore made de Beauvoir obsessed with Olga. Among other legendary works of feminist philosophy, Beauvoir would pen a story titled She Came to Stay, where her author-insert kills a character suspiciously like Olga, to whom the book was also dedicated.
2. Bang Bang, He Shot Me Down
The inspiration for The Great Gatsby still ended in murder. But not Gatsby’s. The famed bootlegger George Remus fell hard in love for Imogene Holmes, whom he later married and let co-run his empire. When she ran off with Remus’s money (and tried to arrange his death), Remus did not take it well. Remus ordered his driver to steer Holmes’s taxi off the road, and then he shot her to death.
After pleading “insanity,” this pseudo-Gatsby died with no money, but he also had zero regrets about shooting his Daisy.
1. Can’t Water Down the Truth
There’s plenty of ghoulish facts to mine about poet Percy Bysshe Shelley and Frankenstein author Mary Shelley (nee Godwin). 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 I think we need to look at the big picture: when they began their relationship, Percy was 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, it was a suicide, but that’s still a grim start to an otherwise productive literary union.