All’s Fair In Love

History is packed with sweeping romances that sound like they belong in a fairy tale, but plenty of them took a seriously dark turn at the very end. While you might complain about a bad breakup or a terrible ghosting experience, these historic couples had to deal with the literal chopping block for their romantic choices. From royal scandals that rocked entire empires to wartime betrayals that sealed a couple's fate, these lovers learned the hard way that passion can sometimes be a health hazard.

Sailko on Wikimedia

1. Anne Boleyn and King Henry VIII

Henry’s intense obsession with Anne changed the course of religion in England, but he quickly grew impatient when she didn’t provide him with a male heir. Henry fabricated outrageous accusations of adultery and treason to escape his marriage. Anne lost her head for her affair at the Tower of London.

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2. Cleopatra and Mark Antony

After losing a massive naval battle to Octavian, they realized their golden days in Egypt were officially over. Antony chose to fall on his own sword after hearing a false rumor about his queen's demise. Cleopatra could not bear the thought of being paraded through Rome as a prisoner, so she famously turned to a venomous snakebite.

Bust: unknown ancient Roman artist of the 1st century AD; photo: unknown photographer. on Wikimedia

3. Catherine Howard and Thomas Culpeper

His fifth wife, Catherine, started an incredibly risky affair with one of the king's favorite male courtiers, Thomas Culpeper.

Love letters between the two were eventually discovered by the king's furious councilors, which meant doom for everyone involved. Culpeper was beheaded for his backstage romance, and young Catherine met the exact same fate.

Hans Holbein the Younger on Wikimedia

4. Mary, Queen of Scots and Lord Darnley

Darnley grew incredibly jealous of Mary's close bond with her private secretary, David Rizzio, and ended his life right in front of the pregnant queen. Revenge came swiftly when Darnley's residence mysteriously blew up, and he was found smothered in the garden outside. Mary was eventually executed years later for separate political plots.

Renold Elstracke on Wikimedia

5. Peter III and Catherine the Great

Peter III was an eccentric emperor who preferred playing with toy soldiers over ruling Russia or spending time with his brilliant wife. Catherine organized a massive military coup with the help of her handsome lover, Grigory Orlov, to seize total control of the throne. Peter was arrested during the chaos and conveniently passed away in custody under highly suspicious circumstances just a week later.

After Alexander Roslin on Wikimedia

6. Lady Jane Grey and Lord Guilford Dudley

Jane was crowned Queen of England for just nine short days before Mary Tudor swept into London to claim her birthright. The young newlyweds were immediately locked away in the Tower of London while the new regime figured out what to do with them. Both Jane and Guilford were led out to the chopping block.

Unidentified painter on Wikimedia

7. Inês de Castro and Prince Peter of Portugal

Prince Peter fell madly in love with his wife's lady-in-waiting, Inês, and continued the affair even after his spouse passed away. Peter's father, King Afonso, absolutely hated the political implications of this relationship and ordered three assassins to execute Inês in front of her children. Years later, Peter dug up her body and forced the nobility to kiss her hand.

Nuno Gonçalves on Wikimedia

8. Julius Caesar and Cleopatra

Before she met Mark Antony, Cleopatra managed to completely charm the most powerful dictator in Rome. Their passionate affair resulted in a son and caused absolute outrage among the conservative Roman senators. Her Roman romance essentially triggered the end of the Roman Republic.

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9. Marie Antoinette and King Louis XVI

They tried to escape the growing chaos in Paris by disguising themselves as common servants and fleeing toward the border in a carriage. They were recognized at a small checkpoint and brought back to the capital to face treason charges from the angry public. Both Louis and Marie Antoinette eventually faced the guillotine.

After Jean-Baptiste André Gautier-Dagoty on Wikimedia

10. Nicholas II and Alexandra Feodorovna

As the country collapsed into civil war, the royal family was captured by Bolshevik forces and hidden away in a Siberian house. One July night, the couple and their children were led down into a basement under the pretense of taking a group photograph.

Instead of a camera, a squad entered the room and executed the entire family.

A. A. Pasetti on Wikimedia

11. Bonnie Parker and Clyde Barrow

Bonnie and Clyde spent years driving across the Midwest, robbing banks and attacking law enforcement officers who got in their way. Their highly publicized crime spree came to a sudden halt in Louisiana when a posse of police officers set up a hidden roadside ambush. The lawmen opened fire on their stolen car without warning.

Buck Barrow on Wikimedia

12. Charlotte Corday and Jean-Paul Marat

Charlotte Corday was a young Frenchwoman who believed that the radical journalist Jean-Paul Marat was ruining the country with his violent writings. She gained access to his private bathroom by pretending to harbor a list of traitors and attacked him while he soaked in his tub. Corday was immediately arrested on the spot and went to the guillotine.

Paul-Jacques-Aimé Baudry on Wikimedia

13. Edith Thompson and Frederick Bywaters

The two wrote hundreds of passionate, highly detailed love letters that frequently daydreamed about getting rid of Edith's boring husband. One night, Frederick attacked the husband on the street and ended his life while Edith watched in complete horror. The authorities used those spicy love letters as absolute proof of a conspiracy, and both lovers met their demise.

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14. George Boleyn and Jane Parker

Being related to Anne Boleyn was a massive hazard to your health during the Tudor era. George was Anne's devoted brother, and he was swept up in the exact same treason charges that brought down the queen.

His own bitter wife, Jane Parker, actually provided the false testimony that sealed his fate on the executioner's block.

George Cruikshank on Wikimedia

15. Tsarevich Alexei and Maria Hamilton

The eldest son of Peter the Great, Alexei, absolutely hated his father's brutal policies and decided to flee Russia with his mistress, Maria Hamilton. They tried to hide out in Europe, but Peter's spies tracked them down. Maria was later executed by beheading.

Johann Gottfried Tannauer on Wikimedia

16. Robert Devereux and Queen Elizabeth I

The Earl of Essex thought he could bypass the aging queen's authority and eventually launched a terrible, failed rebellion in the streets of London. Elizabeth was completely heartbroken by his betrayal but knew she had to maintain her royal authority. She signed his execution warrant, and her former favorite met his end inside the Tower grounds.

Unidentified painter on Wikimedia

17. Thomas Seymour and Queen Catherine Parr

Thomas Seymour was an absolute wild card who used the marriage to get closer to the future Queen Elizabeth I, who was living in their household. After Catherine passed during childbirth, Thomas tried to kidnap the young King Edward VI in a bizarre bid for political dominance. His clumsy power grab failed spectacularly, and he was promptly executed for high treason by his own brother.

After Master John on Wikimedia

18. Arthur Capel and Elizabeth Morrison

During the chaotic English Civil War, Lord Arthur Capel fought bravely for the royalist cause while his devoted wife, Elizabeth, managed their family estate.

Arthur was captured by Parliamentary forces after a brutal siege and locked away in the grim Tower of London. Elizabeth spent all her money trying to bribe guards and petition Parliament for his release, but the revolutionary government wanted to make an example of him.

Cornelis Janssens van Ceulen on Wikimedia

19. Maximilien Robespierre and Éléonore Duplay

They were reportedly engaged to be married once the chaotic revolution finally settled down into peaceful times. That wedding never happened because Robespierre's political enemies turned the tables on him during a dramatic government coup. He was dragged off to the very same guillotine he used on thousands of others.

Unidentified painter on Wikimedia

20. Caroline Matilda and Johann Friedrich Struensee

The young British princess Caroline Matilda found comfort in the arms of the king's brilliant royal physician, Johann Friedrich Struensee. The conservative Danish nobility absolutely hated the doctor's radical reforms and his obvious affair with the lonely queen. They launched a coup, banished Caroline from the country forever, and publicly executed Struensee.

Carl Daniel Voigts on Wikimedia