Six Women Who Dodged a Bullet, or Axe, by Not Marrying Henry VIII

Henry VIII’s marital history is legendary for all the wrong reasons. This Tudor king wed six women in his quest for a healthy male heir and personal satisfaction, and the outcomes were grim for many of them. Two wives were cast aside by annulment, two were executed, one died giving birth, and only the last managed to outlive him. 

It’s no wonder that being Henry’s queen was often more a death sentence than a fairy tale. Yet beyond the six he did marry, Henry considered other women as potential brides. These were the near-misses, the women who, through luck, wit, or circumstance, managed to avoid becoming Henry VIII’s wife. 

Each had been under serious consideration at one point, but all escaped that perilous honor. Here are their stories, with a look at the political stakes, personal motives, and the consequences of their narrowly averted marriages to England’s notorious king.

Eleanor of Austria – The Habsburg Alliance That Never Was

Long before Henry VIII defied the Pope to marry Anne Boleyn, an earlier marriage plan nearly changed the course of his life. In the early 1500s, Henry was a teenager and not yet king. His father, Henry VII, was maneuvering to secure the best possible bride for him. One prime candidate was Eleanor of Austria, a princess from the formidable Habsburg dynasty.

Eleanor was the daughter of Philip of Burgundy and Juana of Castile (known as “Juana la Loca”), which made her the sister of the future Holy Roman Emperor Charles V and a niece of Henry’s first wife, Catherine of Aragon. In other words, she came from the most powerful royal family in Europe.

Henry VII and his wife, Elizabeth of York, saw great advantage in forming an alliance with the Habsburgs. By marrying Eleanor, young Prince Henry would link England to the empire that straddled Spain, the Low Countries, Germany, and Italy. Not only were the Habsburgs politically aligned with England at the time, but Eleanor also promised a rich dowry and international clout. 

In 1506, fate even delivered Eleanor’s family into Henry VII’s hands: her parents (Philip and Juana) were shipwrecked in England and became involuntary guests at the English court. The opportunistic Henry VII took the chance to negotiate a double alliance. He proposed marrying Prince Henry to Eleanor, and Henry’s daughter Mary Tudor to Charles V. The outline of this grand plan was in motion by 1507.

However, there were a few catches. Eleanor of Austria was just a child (she was around eight years old in 1506, seven years younger than Henry), so any actual wedding would be years away. More importantly, Prince Henry himself was not enthusiastic. He had grown up alongside Catherine of Aragon, who by then was a beautiful young widow living at the English court after the death of Henry’s elder brother, Arthur. 

Henry had been enchanted with Catherine for years. Marrying a girl he had never met, one reputed to be less attractive and who wouldn’t be marriageable until she grew up, held little appeal when Catherine was right there and already of age. The prince’s personal feelings ultimately won out over his father’s dynastic scheming. 

When Henry VII died in 1509, the new King Henry VIII immediately took matters into his own hands and married Catherine of Aragon just weeks after his coronation. This bold move ended the negotiations for Eleanor’s hand. The Habsburg princess who might have become Queen of England never even set foot there.

Eleanor went on to play her part on the European stage. In 1518, she married King Manuel I of Portugal, becoming Queen of Portugal, only to be widowed soon after. Then, in a twist of fate, she married Henry VIII’s great rival, King Francis I of France, in 1530. That marriage was part of a peace treaty between Francis and her brother, Emperor Charles V. 

In hindsight, Eleanor of Austria likely counted herself fortunate. Had Henry VII’s plan succeeded, she would have been Henry VIII’s first wife instead of Catherine of Aragon. Given Henry’s later pattern of discarding wives who didn’t produce a male heir, Eleanor might have met the same fate as Catherine, a painful divorce or worse, once Henry’s wandering eye and dynastic desperation took hold. 

Mary of Guise – The French Dowager Who Defied the King

By 1537, Henry VIII was back on the marriage market, and the stakes were high. He finally had a precious male heir, the newborn Prince Edward, thanks to his third wife, Jane Seymour. But Jane had died from childbirth complications, leaving Henry a widower at age 46 with a tiny son to secure the Tudor lineage. 

Henry’s advisers were eager to find him a new queen, preferably one who could bolster England’s political position and potentially provide a “spare” male heir. In this hunt, Henry’s gaze turned abroad once more, and one name shone brightly: Marie de Guise.

Mary of Guise was a prize on the European marriage market. At 21 years old, she was a French noblewoman from the powerful House of Guise, a family with significant influence in French politics and strong Catholic credentials. Despite her youth, Mary was already a widow. Her first husband, the Duke of Longueville, had died, leaving her with a young son and a substantial fortune. 

Descriptions of Mary at the time praised her stature and presence: she was tall (reportedly around 5’11”), which was unusual and striking for a woman of that era, and she was considered attractive, intelligent, and capable. Importantly for Henry, her French royal connections made her an enticing candidate. 

By marrying Mary, Henry could create an alliance with France and potentially undermine Scotland, England’s northern rival. Why Scotland? Because the newly widowed Mary of Guise had also caught the eye of James V of Scotland. In fact, James was actively courting her as his next queen. If Henry could snatch her up instead, it would be a double win: a prestigious French bride for himself and a blow to the Scots.

Henry’s interest in Mary of Guise was no secret. He had his ambassador in France inquire about her, and according to one story, Henry boasted to the French that a big man like himself needed a big wife, a rather crass way of saying Mary’s height and robust health were appealing since Henry was a large man. 

When this comment got back to Mary, she delivered one of the most famous quips in Tudor lore. With razor-sharp wit, she said, “I may be a big woman, but I have a very little neck.” This jibe was a pointed reference to Henry’s habit of beheading wives who displeased him. Mary of Guise made it clear she wasn’t keen on risking her neck with England’s volatile king.

Wit aside, Mary had practical reasons to reject Henry’s advances. She was a devout Catholic and France’s ally; Henry was excommunicated and had created his own church. Also, Henry was 46, obese, and notoriously unpredictable in marriage, not an enticing prospect for a young widow. 

In contrast, James V of Scotland was closer to Mary’s age (mid-20s), shared her faith, and was actively supported by the French in wooing her. King Francis I of France, who was Mary’s patron, certainly preferred to see her on the Scottish throne, cementing the traditional “Auld Alliance” between France and Scotland, rather than see her become Queen of England and potentially patch things up between Henry and the French.

In the end, Henry VIII lost this round of the matrimonial chess game. Mary of Guise chose Scotland. She married James V by proxy in May 1538 and shortly after in person, becoming Queen of Scots. Henry’s reaction was bitter. He had been outmaneuvered. This loss had real consequences. Because Henry didn’t get Mary, he failed to forge a France-England alliance and couldn’t extend English influence over Scotland through marriage. 

In fact, Mary of Guise’s marriage tightened the Franco-Scottish bond. She would later give birth to a daughter, Mary Stuart (Mary, Queen of Scots), in 1542, a baby who immediately became a new thorn in England’s side as a Catholic claimant to the English throne.

Mary of Guise’s life in Scotland wasn’t exactly peaceful (she endured the deaths of her husband and sons, and governed as regent for her young daughter through tumultuous times), but she unquestionably dodged a bullet by not becoming Henry’s wife. 

Instead of a dangerous life at the English court, Mary carved out her own legacy as the savvy Regent of Scotland, facing challenges that were formidable but at least not coming from a tyrannical husband. For Henry, missing out on Mary of Guise was a blow to his pride and plans. It forced him to cast his net elsewhere in search of wife number four, as we’ll see next.

Christina of Denmark – The Duchess Who Valued Her Head

If one woman epitomized the idea of “escaping” Henry VIII, it was Christina of Denmark. In 1538, this teenage noblewoman looked Henry’s matrimonial offer in the eye and said, “No thanks,” with a memorable twist. Christina was just sixteen, beautiful, and already a widow. 

Born a Danish princess, she was the niece of Charles V, the Holy Roman Emperor, and had been married off at age eleven to the Duke of Milan. That marriage left her a duchess and, by 1538, a rich young widow with impeccable Habsburg pedigree. In other words, prime queen material on the European stage. 

After Jane Seymour’s death, Henry VIII was eager to find a new bride who could give him another son and perhaps repair relations with Catholic Europe. Marrying Christina of Denmark would have killed two birds with one stone: Henry would ally himself by marriage to his former ally-turned-enemy Charles V (Christina’s uncle), potentially easing the isolation England faced after breaking from Rome.

Henry’s minister, Thomas Cromwell, pulled out all the stops to woo Christina. This courtship was like something out of a royal art auction. Henry hadn’t met Christina in person, so he sent his court painter, Hans Holbein the Younger, to Brussels to paint her portrait. Holbein was instructed to make it as lifelike as possible, as Henry wanted to judge the girl’s appearance before committing. 

Christina obliged the painter, sitting for the portrait dressed in mourning black (she was still in formal mourning for her late husband) and reportedly comporting herself with grace and poise. The famous resulting painting shows a slender young woman with large dark eyes, a composed expression, and an elegant black gown. Henry, upon seeing Holbein’s work, was smitten enough to proceed with the match, on paper, at least.

But Christina of Denmark was not an eager bride, especially not eager to wed Henry. She had heard all about the English king’s track record with wives. How could she not? By 1538, Henry was the European gossip topic of the decade: the king who had set aside one wife, executed another, and lost a third in childbirth, all within a few years. Christina’s own great-aunt, Catherine of Aragon, had been the first discarded wife, and Catherine’s mistreatment did not endear Henry to the Habsburgs. 

Christina, despite being young, had a sharp understanding of the situation. According to later reports, when asked about the possibility of marrying Henry, she dryly quipped that if she had two heads, she would happily put one at the disposal of the King of England. This bold statement encapsulated the sentiments of many in Europe. Henry VIII was seen as a dangerous husband.

Of course, being a royal woman, Christina couldn’t simply decide her fate alone. Her uncle, Emperor Charles, and her aunt, the Regent of the Netherlands (Queen Mary of Hungary), had a say. In truth, Charles V was lukewarm about tying his family to Henry at that moment. Henry’s break from the Catholic Church and his subsequent alliances shifted him into an unreliable partner. 

While negotiations with England continued through 1538, they dragged on and stalled. Christina’s guardian, Mary of Hungary, wasn’t enthusiastic about sending her favorite ward into the lion’s den of the English court. And Christina herself made no secret of her reluctance. It became obvious that this match was going nowhere. 

Henry’s ambassadors reported back that the imperial court was just stringing them along. Charles V had too many conflicts of his own (with France, with the Protestant princes in Germany) and decided that appeasing Henry VIII wasn’t worth sacrificing his young niece. Henry was finally advised to “fix his stomach elsewhere”. The negotiations were formally abandoned. Henry never got his Habsburg bride.

Christina went on to a different life entirely, one far removed from the English throne. In 1541, she married Francis, Duke of Lorraine, which further secured her position in European high society. Christina became a Duchess once more, had children, and lived to the age of 62.

Amalia of Cleves – The “Backup” Bride Who Stayed Home

Henry VIII’s fourth marriage is infamous in its own right, the ill-fated union with Anne of Cleves. However, less well known is that Anne of Cleves had a younger sister, Amalia (also spelled Amelia), who was also considered a possible royal bride. In 1539, after the collapse of the Christina of Denmark negotiations, Henry’s chief minister, Thomas Cromwell, pivoted to a Protestant alliance. 

England was isolated from Catholic Europe, so Cromwell sought ties with the Lutheran princes in Germany. The Duchy of Cleves, located on the Rhine, was a significant player among the German states. Its ruler, Duke William, had two unmarried sisters available: Anne, aged 24, and Amalia, a few years younger at 22. The idea was that Henry might marry one of them to seal an alliance with Cleves and its Protestant allies.

As was customary, Henry dispatched Hans Holbein to capture the likenesses of the Cleves sisters so he could choose between them. Holbein painted Anne (and possibly Amalia, though that portrait is lost or unconfirmed). The portrait of Anne of Cleves famously pleased Henry. It showed Anne in rich clothes with a calm, modest expression. She seemed agreeable and attractive enough in the painting. 

Based on reports and the portrait, Henry agreed to marry Anne. However, it was understood that Amalia of Cleves was essentially waiting in the wings as a backup option. In diplomatic marriages, it wasn’t unusual to consider multiple sisters from a royal house, just in case the elder was unsuitable or negotiations faltered. So, while Anne traveled to England in winter 1539 to become queen, Amalia stayed home but on standby.

Then came the disaster. Henry met Anne of Cleves in person in January 1540 and was instantly repulsed. The poor woman just didn’t live up to his lustful expectations. Henry infamously complained about Anne’s looks and body, claiming he found her unattractive and that he could not kindle any passion for her. Modern interpretations suggest that Anne was likely perfectly normal in appearance; the issue was Henry’s own mindset, and perhaps Anne’s lack of sophistication in English courtly flirtation. 

Whatever the cause, Henry wanted out of the marriage almost as soon as it began. Now, logically, one might think this would be the moment to swap in the younger sister Amalia, since she was available and presumably might be more to Henry’s liking. But Henry VIII’s pride had been wounded. 

He had felt embarrassed by what he saw as a “false advertising” situation with Anne’s portrait, and he wasn’t inclined to trust any Cleves woman now. It also didn’t help that Anne of Cleves herself reportedly found Henry gross and unappealing (though she wisely never said so openly at the time). The whole Cleves match had turned sour.

For Amalia, this outcome meant she remained safely at home in Cleves. She never married anyone. Perhaps her prospects were hampered by the very public way her sister’s marriage had collapsed, or perhaps she simply didn’t find a match of her liking afterward. In any case, Amalia lived out her life in the German states, far removed from Henry VIII’s dangerous matrimonial carousel. 

Anna of Lorraine – The Almost Fourth Wife You’ve Never Heard Of

Not every bride Henry considered is famous today; some plans barely got off the ground. One such blip on the radar was Anna of Lorraine, a high-born European princess who was floated as a possible match in the early 1540s. Anna doesn’t feature in many Tudor dramas, but at the time, her name carried weight. 

She was a daughter of the Duke of Lorraine, born in 1522 into a family connected to both the French royal house and the Habsburgs. In fact, her family, the House of Lorraine, was entwined with the powerful Guise clan in France and also had ties to Emperor Charles V through marriages. This made Anna a politically attractive candidate for any king in search of a bride with continental alliances.

The notion of Henry marrying Anna of Lorraine came up in the aftermath of the Anne of Cleves debacle. In 1540, after he had annulled that marriage, Henry was once again theoretically wife-hunting. His advisors (what was left of Cromwell’s faction and others) still thought a foreign alliance could be beneficial. 

Anna of Lorraine fit the bill on paper: she was about 18, presumably attractive, and from a prominent Catholic family that might help reconcile Henry with either France or the Empire. There’s evidence that her name was suggested to Henry, and perhaps informal feelers were sent out to gauge the possibility.

However, Henry’s willingness to jump into another international marriage was virtually nil by that point. He famously questioned the reliability of portraits and ambassadors’ descriptions after being “deceived” (in his view) about Anne of Cleves. So even though Anna of Lorraine might have been an appealing option under other circumstances, in 1540, Henry wasn’t eager to roll the dice again on a young woman he hadn’t met. 

To complicate matters further, Henry’s attention had already been captured by Catherine Howard, a lively 19-year-old lady-in-waiting who happened to be the first cousin of his late second wife, Anne Boleyn. By summer 1540, while whispers of Anna of Lorraine floated in diplomatic channels, Henry was secretly arranging to marry Catherine Howard, which he did just weeks after annulling Anne of Cleves. That essentially torpedoed any chance for Anna of Lorraine to become Queen of England.

From Anna’s side, there were other developments too. In a striking coincidence of timing, Anna of Lorraine got married herself in late August 1540, to Prince René of Châlon, the Prince of Orange. This was a notable match in its own right: René was a sovereign prince in the Low Countries and a prominent noble. She likely never seriously considered Henry’s offer, if a formal offer ever reached her, because her family had secured this other prestigious marriage for her. 

Anna’s life took a very different path: she had a short-lived marriage to René of Orange, who died in 1544 in battle, and through a twist in inheritance, René’s title and lands passed to his cousin, the famous William of Nassau (William the Silent). Anna thus indirectly helped shape European history: she was the link between the old House of Orange and the new one that led the Dutch Revolt against Spain. She remarried a few years later to a Dutch duke and lived until 1568, navigating the tumultuous politics of France and the Low Countries.

Katherine Willoughby – The Almost Seventh Wife

By the mid-1540s, one might think Henry VIII would have given up on marriage, but Henry was nothing if not persistent in pursuit of his desires. His sixth marriage, to Catherine Parr in 1543, brought him a steady, mature companion who skillfully managed the blended family of Henry’s children and nursed the aging king’s ailments. Yet even in the twilight of his life, Henry’s eye roamed toward one more potential bride. The lady in question was not a foreign princess at all, but someone much closer to home: Katherine Willoughby, Duchess of Suffolk.

Katherine Willoughby was a remarkable woman of the Tudor court. Born in 1519 to an aristocratic family, she was married at just 14 to Charles Brandon, Duke of Suffolk, who happened to be King Henry’s closest friend. Brandon was around 49 when he wed young Katherine (a match arranged in part for her wealth and titles), so Katherine entered adult life as a teenage duchess married to a man old enough to be her grandfather. 

Despite the age gap, their marriage produced two sons and seemed to be affectionate. Katherine was no demure, sheltered girl; she was known for her keen intellect, outspokenness, and a biting sense of humor. Over the years, she also became an ardent Protestant reformer, very much in line with the religious sympathies of Henry’s later court.

Katherine’s proximity to Henry VIII was significant. She had frequent interactions with him due to her husband’s position and later as a lady-in-waiting. After Jane Seymour’s death in 1537, some at court noticed Henry’s friendly attention toward Katherine Willoughby even as he sought a new bride (which turned out to be Anne of Cleves). In fact, in early 1538, imperial ambassador Eustace Chapuys reported that Henry had been “visiting” Lady Suffolk (Katherine) rather often.

Nothing overt came of that at the time; Henry married Anne of Cleves, then Catherine Howard, then Catherine Parr. Through all this, Katherine Willoughby remained in the king’s orbit. She was a close friend of Catherine Parr (despite having served briefly as a maid to Henry’s earlier queens). So why did Henry’s interest in Katherine resurface? 

By 1545, two things had changed: Katherine Willoughby was widowed (Charles Brandon died in 1545, leaving her a wealthy single woman of 26), and Henry’s marriage to Catherine Parr, though outwardly stable, had not produced any children and had hit a few rocky patches due to religious differences.

There were rumors swirling in 1546 that Henry VIII was considering setting aside Catherine Parr. The king’s temper and paranoia had grown with his age and ill health. At one point, Catherine Parr’s penchant for debating theology nearly landed her in trouble. Henry signed a warrant for her arrest on accusations of heresy, though he never enforced it after Catherine cleverly reconciled with him. 

In those tense days, people at court speculated who might replace Catherine if she fell from favor. Katherine Willoughby’s name emerged at the top of the list for a potential seventh queen. She had several qualities that made her attractive to Henry: she was significantly younger (in her mid-20s, whereas Catherine Parr was in her 30s and Henry was 55), she had proven fertility with two strong sons (a big plus for a king still obsessed with securing his succession), and she was of noble blood with a sharp mind and engaging personality that Henry had long appreciated. 

Yet, Katherine Willoughby was also known to be “fiery” and opinionated, just like Catherine Parr. Henry may have privately admired that spark, but marrying another outspoken Protestant woman when he was already tiring of Catherine Parr’s assertiveness might have given him pause. The chronicles don’t show Henry making any official move to court Katherine Willoughby, but several diplomats wrote as if her becoming queen was a real possibility in 1546. 

In the end, Henry’s health was deteriorating rapidly. He didn’t go through with arresting or divorcing Catherine Parr, and he never proposed to Katherine Willoughby. Henry VIII died in January 1547, still married to his wife number six and leaving Katherine Willoughby as “the one that got away.”

Dodging the Tudor Bullet

Each of these women managed to sidestep the role of Henry VIII’s wife. Their stories are each unique, but all share a common thread of escape from a marital union that could have ended in disaster. In the ruthless world of 16th-century royal politics, marriage was a high-stakes game of alliance-building and survival. For Henry, every match was supposed to secure his dynasty or bolster his power, yet so often it led to personal and political turmoil. For the women, a royal marriage could elevate them to great honor but also put them directly in harm’s way – and no one’s way was more harmful in that era than Henry VIII’s.

The ones who escaped Henry’s grasp often fared better than those who didn’t. They weren’t subjected to his mercurial affections, his growing paranoia, or the literal threat of the executioner’s sword. Instead, they found different paths. Some, like Mary of Guise and Christina of Denmark, went on to make advantageous marriages and wield influence in other courts. Others, like Amalia of Cleves and Anna of Lorraine, lived relatively quiet lives away from the spotlight that would have shone, perhaps harshly, upon them in England. Katherine Willoughby remained her own woman, outspoken to the end, never having had to submit to a king’s will as his bride.