20 Historical Figures Who Chose the Wrong Spouse

Henry VIII’s marriage to Catherine of Aragon, which had begun under the best of circumstances, ended in a veritable religious upheaval on a national scale. When Catherine failed to give him the male heir he desired, Henry did not accept this disappointment with equanimity nor move on with dignity. On the contrary, he pursued the annulment of his marriage with such relentlessness that England ultimately broke with Rome.

Henry VIII made several poor decisions in this regard, and Anne Boleyn was undoubtedly one of them. He annulled his first marriage to be with her, then turned against her with astonishing speed as soon as their relationship soured and she still had not given him a son. That marriage ended in accusations, political maneuvering, and Anne’s execution.

The marriage between Lord Darnley and Mary, Queen of Scotland, almost immediately proved to be a terrible mistake. He was vain, erratic, ambitious, and utterly incompetent—as only a royal spouse with an outsized ego can be. Their marriage became mired in jealousy and ended with Darnley’s murder, in which Mary was likely implicated.

Catherine the Great was married to Peter III, and this union was such a failure that it practically became fertile ground for revolution. Peter managed to alienate the Russian court, appear absurdly immature, and make himself politically undesirable—all at once. Catherine ultimately helped depose him and proved to be far more competent than her husband could ever have been. 

Marie Antoinette was sent to France to marry Louis XVI when she was only 14 years old. Their marriage was not doomed to failure solely because of their personalities, but that certainly did not help either of them cope with what was to come. Louis XVI and Marie Antoinette became the symbol of a monarchy that seemed aloof, indecisive, and completely out of touch with reality, and her unhappy marriage to him ended with her execution by guillotine, along with that of her entire family. 

Napoleon and Josephine shared a true love story, but as a dynastic marriage, this union proved frustrating. She possessed charm, charisma, and influence, but she could not give him the heir he desired—something that mattered immensely to a man seeking to build an empire. This union brought him immense power, great wealth, and security, but it ultimately cost him his marriage and his peace of mind when he divorced her in 1810 in order to secure an heir.

It is hard to imagine a more ill-matched couple than George IV and Caroline of Brunswick, who managed to hate each other with formidable efficiency. Their marriage was disastrous from the start, and both spouses contributed greatly to the public embarrassment that followed. Even as George was about to become king, he was still trying to keep her away from the coronation—not exactly a sign of a happy marriage. 

The marriage of Nicholas II and Alexandra was marked by deep personal devotion, which makes the political consequences all the more painful. Alexandra’s influence at court, particularly during wartime and the Rasputin years, seriously damaged the monarchy’s reputation. Her distrustful nature and Nicholas’s passivity formed a combination that gave the impression of an even more unstable regime in decline, and her marriage to him proved disastrous for her.

Emperor Claudius’s marriage to Messalina turned into one of the most infamous marital disasters in ancient Rome. She earned a reputation as a scheming, debauched, and manipulative woman, and the situation escalated to such an extent that she was eventually executed. 

The marriage of Charles I to Henriette Marie sparked political tensions from the very beginning, as she was an outspoken Catholic in a country already anxious about religion and royal authority. Their mutual affection was sincere, but politically, this union fueled fears that Charles’s reign would drift toward absolutism and Catholic influence. Against this backdrop, the marriage became yet another reason for the people to distrust the crown.

Edward IV’s secret marriage to Elizabeth Woodville may have been romantic, but it caused serious political unrest. His allies had expected an alliance with a foreign power, not a surprise marriage to a widow with complex family ties. This marriage fueled resentment, sparked conflicts between factions, and caused great irritation among the nobility. In 15th-century England, marrying for love was not always the stabilizing solution one might have hoped for.

Edward II and Isabella of France could never have embodied the ideal model of royal happiness. Edward’s preference for his powerful male companions and his inability to manage tensions at court turned their marriage into something far more dangerous than mere personal unhappiness. Isabella eventually turned against him and contributed to his downfall. 

Mary regarded Philip II as an excellent Habsburg match who would help ensure England’s security and strengthen Catholic power. Many of her subjects viewed him as a foreign husband exerting a dangerous influence, and the marriage never produced the heir Mary so desperately desired. It also made her more politically vulnerable in her own country and tied her more closely to unpopular continental interests. 

Caesar’s marriage to Pompeia is best remembered for the disastrous way it ended in terms of his reputation. After the Bona Dea scandal, he divorced her, even though direct evidence of wrongdoing mattered less than the public disgrace that weighed on their household. It was one of those marriages where scandal caused more damage than affection could ever have repaired.

The relationship between Antony and Cleopatra has become the stuff of legend, which sometimes obscures just how politically disastrous it proved to be for him. Whatever the emotional reality of that bond may have been, this union allowed Octavian to easily portray Antony as a compromised, decadent man who was dangerously under the sway of a foreign influence. Such an image was devastating in Roman politics. It is difficult to recover from when one’s alliance—which is akin to a marriage—becomes one’s rival’s strongest campaign argument.

In hindsight, it may not have been the best idea to marry a man nicknamed “the Terrible,” but she probably didn’t really have a choice. Maria was Ivan the Terrible’s eighth and last wife; she was forced to become a nun and died in obscurity. Their union produced Dmitri, whose death later on helped fuel endless mistrust and instability during the ensuing succession crisis. 

Pedro is generally remembered for his affair with Inês de Castro, which speaks volumes about the quality of his marriage to Constance. Constance was his lawful wife, but Pedro’s obsession with Inês turned that union into a tense and deeply awkward dynastic situation. The emotional turmoil surrounding this marriage helped create one of the most famous love stories in Iberian history. It ended with Constance’s death while she was giving birth to their son, the future King Ferdinand I, after which Pedro refused to remarry and chose instead to live openly with Inês.

It was not so much a matter of romantic incompatibility as it was a marriage that fueled ambitions in the wrong direction. George’s marriage to Isabel Neville drew him even deeper into the unstable political intrigues of the War of the Roses. Far from bringing him stability, this alliance became part of a vast web of conspiracies, shifting allegiances, and dynastic self-destruction. 

Oscar Wilde and Constance Lloyd appear on this list on a sadder note, as the problem lay not so much in cruelty as in the disconnect between public expectations and the reality of their private lives. Wilde’s marriage produced children and an outwardly respectable life, but his deepest desires and relationships made this arrangement untenable in the long run. The result was emotional strain, scandal, and a family life ultimately overwhelmed by disaster. 

This one is more complex than many others, because Abraham and Mary Todd Lincoln shared intelligence, ambition, and a genuine bond. Yet their marriage was notorious for its turbulence and appeared unhappy from the outside, marked by emotional tensions, financial difficulties, grief, and Mary’s instability in the face of immense pressure. It was a marriage defined by intensity rather than serenity, and serenity might have been more beneficial for both of them.