The 20 Most Inappropriate Relationships in History

The Roman emperor Nero was no stranger to… relationships that were, to say the least, unusual (if one can even call them that). He ordered the death of his wife, Poppaea Sabina, in 65 CE, although the exact circumstances of this event are still a matter of debate. Later, he had a young freedman named Sporus castrated and took part in a public wedding ceremony with him, presenting Sporus in the role of a bride. 

Cleopatra VII met Julius Caesar in Alexandria in 48 B.C., while she was fighting her brother for control of Egypt. Caesar was married to Calpurnia in Rome, but Cleopatra eventually gave birth to a son, whom she presented as Caesar’s child. When Cleopatra later traveled to Rome, her presence only exacerbated the political unease caused by Caesar’s rise to power and his ties to her.

Caesar was not the only one who had ties to Cleopatra. Mark Antony also became friends with her after Caesar’s death. At the time, Antony was married to Octavian’s sister, but he spent long periods in the eastern Mediterranean with Cleopatra and acknowledged their children. Octavian took this as a personal offense, used Antony’s relationship with Cleopatra as part of his campaign against him, and the whole affair ended with the suicides of Antony and Cleopatra in 30 B.C.

Around 1115, Pierre Abélard was hired to tutor Héloïse, the highly educated niece of Fulbert, a canon at Notre-Dame de Paris. It wasn’t long before their relationship resulted in a child, and the couple married in secret. As might be expected, this story ended disastrously: Fulbert’s supporters later turned on Abelard and castrated him, after which Abelard became a monk and Heloise took her vows.

Rosamund Clifford developed a close friendship with King Henry II even though he was already married to Eleanor of Aquitaine. Henry’s favor toward Rosamund only fueled rumors and was even widely reported in later accounts, although many of the most dramatic stories surrounding her death are more legend than fact. She died around 1176 and was buried at Godstow Abbey, where her connection to the king continued to be remembered.

As we all know, history is full of mistresses and secret affairs, and John of Gaunt was no exception. The Duke of Lancaster had a long-term relationship with Catherine Swynford while he was married to Constance of Castile. Catherine had been part of his household, and their children had already been born before the couple married in 1396. These children were later legitimized under the name Beaufort.

Henry VIII courted Anne Boleyn while he was still married to Catherine of Aragon, a marriage he had maintained for more than twenty years. His campaign for an annulment led to a break with papal authority and the establishment of royal supremacy over the Church of England. But things were not all rosy for Anne. True, she became queen in 1533 and gave birth to the future Elizabeth I, but she was also executed in 1536 for adultery and treason.

Catherine Howard married Henry VIII in 1540, becoming the king’s fifth wife while she was still a teenager. Evidence later revealed that she had had private meetings with Thomas Culpeper, a gentleman of the privy chamber, and that Lady Rochford had helped facilitate these meetings. Culpeper was executed in 1541, and Catherine was beheaded in 1542.

Mary, Queen of Scotland, married James Hepburn, Earl of Bothwell, in 1567, just a few months after the assassination of her second husband, Lord Darnley. Bothwell was tried and acquitted of Darnley’s murder, but many nobles remained deeply hostile to his rise to power. They apparently had good reason to be, for this marriage helped spark an armed rebellion and led to her forced abdication in favor of her infant son, James VI.

Robert Dudley held an exceptionally privileged position at the court of Elizabeth I from the very beginning of her reign. Dudley was married to Amy Robsart, but her death in 1560 was the subject of intense speculation, largely attributed to a fall that occurred at Cumnor Place. Although Elizabeth never married Dudley, she kept him among her closest friends and elevated him to the title of Earl of Leicester.

George Villiers rose relatively quickly through the ranks at the court of James I after catching the king’s attention in the 1610s. This did not sit well with those around him, especially since James granted him everything one could have dreamed of at the time: titles, offices, estates, and privileged access. Villiers even managed to become Duke of Buckingham. Their correspondence was also marked by a strange affection, and Villiers quickly became one of the most hated political figures in England.

Françoise-Athénaïs de Rochechouart became Louis XIV’s mistress while continuing to serve Queen Marie-Thérèse. She was also married at the time, but she nevertheless had several children by the king, many of whom were later legitimized.

Jeanne Bécu, who later became Madame du Barry, became the official mistress of Louis XV toward the end of his reign. Her background and life story were particularly unpopular among members of the old aristocracy. She was not well-liked by the public, and after the French Revolution, she was arrested, tried, and executed in 1793.

Lucrezia Borgia married Giovanni Sforza in 1493, while she was still a teenager, as her father, Pope Alexander VI, sought to forge an alliance with Milan. Once the marriage had lost all its appeal, the affair ended in utter chaos, with conflicting accounts. Alexander had the marriage annulled, claiming that Giovanni was impotent—an accusation that Giovanni publicly denied. Sforza retaliated by accusing Lucrezia of having had affairs with her father and brother, which helped cement the Borgia family’s scandalous reputation.

Lord Byron was already infamous for his romantic escapades, but he somehow managed to tarnish his reputation even further when rumors began to circulate about his relationship with his half-sister, Augusta Leigh. In 1814, Augusta gave birth to a daughter, and some believed Byron was the father. This scandal contributed to the collapse of his reputation in England, and he left the country for good barely two years later.

Sally Hemings was a slave at Monticello; she had joined Jefferson’s household through his wife’s family. Research supports the conclusion that Jefferson was the father of several of Hemings’ children. A DNA study conducted in the 1990s established a link between Jefferson’s male-line descendants and the descendants of Eston Hemings, thereby calling into question an earlier hypothesis that Jefferson’s nephews, the Carrs, were the fathers of Hemings’ children.

Edgar Allan Poe married Virginia Clemm in Richmond in May 1836. All of this seems perfectly fine, until one recalls two crucial facts: Poe was 27 at the time, while Virginia was only 13—and she was also his first cousin. She died of tuberculosis in 1847, and the grief he felt as a result left a deep mark on his later works.

Eloping with a new lover was a major event in the Victorian era, and no one knew this better than Effie Gray. She married the famous art critic John Ruskin in 1848, but their marriage was annulled barely six years later on the grounds that it had not been consummated. To make matters worse, Effie had also become close to the painter John Everett Millais while he was working on Ruskin’s portrait—and while he was still married to Effie. Effie married Millais after the annulment, and this ordeal sparked a sensational scandal.

Charles Dickens met the actress Ellen Ternan in 1857, while he was preparing a play in Manchester. Again, this all seems perfectly fine until one remembers that Dickens was 45 and Ternan was 18. In any case, he separated from his wife the following year, after more than 20 years of marriage, and this relationship was carefully concealed during his lifetime.

Charlie Chaplin married Lita Grey in 1924, when she was 16 and he was 35. Even more troubling was the fact that Lita Grey had appeared in Chaplin’s films from a very young age, and their marriage took place after she became pregnant. Their divorce caused a scandal in 1927, tarnishing Chaplin’s public image.