The simplest answer as to what Henry wanted from women may be the most obvious: a son. But a rational response to desiring and not receiving a legitimate male heir, even in the 16th century, wasn’t to form your own religion or behead your wife. Furthermore, Henry went through three more wives after his son, the future Edward VI, was born in 1537. Clearly “a son” wasn’t the only factor at play in Henry’s motivations for taking and discarding wives. So, what was going on?

A primer for those that aren’t familiar with the history:

1. Katherine of Aragon: A princess of Spain, Henry married her in 1509 just before his 18th birthday. Despite several pregnancies, the only living child she delivered him was a daughter, the future Mary I, in 1516. By 1520 her childbearing years were behind her, her figure and looks had long been lost due to the physical toll of pregnancy and childbirth and she became increasingly religious. She refused to step aside when Henry sought a divorce, leading to a seven year battle royale that ended in their divorce and England’s break from Rome. She died, still maintaining she was the true queen, in 1536.
2. Anne Boleyn: The most famous of Henry’s wives and rightfully so. Educated in France and sympathetic to the “reformed” faith, she arrived in England in the early 1520s just as Henry was beginning to contemplate measures to leave Katherine. They began an emotional affair that reportedly stayed non-physical because Anne refused to sleep with Henry before marriage. She managed to keep his attention and inspire the King to move mountains for the better part of a decade before a brief three-year marriage that ended in her arrest and execution on charges of adultery and incest. Like Katherine, she had multiple pregnancies, but only delivered one healthy child, the future Elizabeth I.
3. Jane Seymour: A lady-in-waiting to Katherine and Anne before her, she was approaching spinsterhood at the Tudor court before she caught Henry’s eye during one of Anne’s pregnancies. Like her predecessor, she refused to sleep with Henry before marriage and 24 hours after Anne’s execution she and Henry were betrothed. She gave birth to Henry’s one and only legitimate son, Edward VI, in October 1537 before succumbing to childbed fever.
4. Anne of Cleves: The second foreign alliance made by Henry, she was shipped in from Cleves, Germany for her Protestant faith by the members of the English government who were keen to sideline the Catholic faction. Henry took a quick dislike of her for reasons that aren’t entirely clear, tried to back out of the marriage before the wedding, and then refused to consummate it on the grounds she was too unappealing. Unlike Katherine, Anne didn’t fight a divorce and accepted a deal that included an allowance and the role of the “King’s sister” at his court. She lived out the rest of her days in England with varying theories as to whether she was happy or unhappy to be rid of Henry.
5. Katherine Howard: Henry’s child bride and a younger cousin of Anne Boleyn’s, Katherine came to court as a lady-in-waiting to Anne of Cleves. She likely caught the King’s eye before or during his fourth marriage and he married her once his divorce was finalized in the summer of 1540. Uneducated, naive and possibly the victim of child abuse, she was essentially framed in the autumn of 1541 and arrested and executed in the winter of 1542 for premarital relationships and adultery. More on that here.
6. Katherine Parr: Henry’s last wife and for whom he was her third husband. As a widow, she neatly sidestepped the question as to whether she was a virgin or not and managed to outlive Henry, but only by a hair. She came very close to her own arrest towards the end of 1546 and saved herself with some smooth talking. She is most famous for reconciling Henry with all of his children, but she *should* be known for her authorship and scholarship. She went on to marry Thomas Seymour, Jane Seymour’s brother, after Henry’s death (because things weren’t incestuous enough) and died of childbed fever in 1548.

So, there you have it – the six wives of Henry VIII. But the most important woman in Henry’s life wasn’t one of his wives, nor was it one of his two famous daughters: It was the least well-known of the lot, his mother. In my opinion (shout out to Freud), much of this comes back to the mysterious figure of Elizabeth of York. And if you aren’t familiar with her trajectory, then I would point you here.

Henry was, rather famously, born a second son and I think that’s key for a number of reasons. First and foremost, it meant that he, unlike his elder brother, Arthur, was brought up by his mother and raised with his sisters. For a man that had such a complicated and violent relationship with women, Henry grew up surrounded by them in a court dominated by their influence. His father, Henry VII, was devoted to his own mother, Margaret Beaufort, Countess of Richmond, and his mother had three sisters who circled in and out of court giving him a plethora of female relations.

Secondly, it meant that for the first 10 years of Henry’s life, he was intended for the church. The great irony, then, is that he was raised for celibacy and trained for the masculine hierarchy of the Catholic Church.

There is sometimes a hesitancy to give Elizabeth too much weight in Henry’s life, to offer too much of an armchair analysis. To that I say, why? It’s impossible to discuss a man with Henry’s marital history and not look at his mother, and then once you’ve done so and realize she died when he was young, not raise your eyebrows at least a little bit.

Her death was a shadow of what was to come. In 1501 Henry first truly careened on to the public stage when Katherine of Aragon arrived in England to marry his brother, Arthur. He stole the show at the wedding banquet by throwing off his doublet and dancing to the delight of the assembled guests. Five months later Arthur was dead, Katherine returned to London and Henry’s life was forever altered. No longer was he meant for the church; he was the next king of England.

Henry VII and Elizabeth were devastated by their son’s death, but (chillingly with hindsight) when comforting her husband Elizabeth told him they were still young and could beget more children. Within weeks she was pregnant again, despite there being a several-year gap since her last pregnancy, indicating she went about having another child solely to provide her husband with a backup male spare. The infant was a girl who didn’t live long and Elizabeth died a few days after giving birth on her 37th birthday.

In the span of less than a year England had lost its Prince of Wales and its queen, but Henry had lost his brother and his mother. It was the latter that was the biggest blow and it begs the question, what did he understand and what did he take away from the fact that attempting to provide another boy cost his beloved mother her life?

Not for nothing, but his third wife, Jane, died in similar circumstances. Henry would later refer to her as his favorite wife and, even after taking other wives, it was she that he featured in portraits that glorified the Tudor dynasty as the mother of his son. We don’t know enough about her personality to glean whether her demeanor was similar to Elizabeth’s, but for that matter, we don’t know much about Elizabeth’s. In short, they were two women who largely stayed out of the frame and were sacrificed at the altar of the House of Tudor.

But Jane wasn’t the great love of Henry’s life, not really. Anne Boleyn was. It wasn’t a romantic love, though it started out the way, but it was a passion. A passion that made Henry turn the world upside down, break away from the Church to which he had been devoted, push away a daughter who he had once adored and execute any and all friends who dared stand in his way. But like many passions, it took an ugly turn when Anne didn’t hold up her end of the bargain and, for all intents and purposes, he had her murdered.

It is worth considering two things: 1) The woman who drove the greatest intensity in Henry was the one least like Elizabeth and 2) His irritation stemmed, in large part, from her inability and unwillingness to assume the same role that Elizabeth had – a mother of sons, a domestic force, a quiet, feminine presence.

It’s the second point that gets interesting, for it draws up that what Henry loved and what Henry sought in a wife were two different things – a conflict not unique to Henry by any means. But what is evident from Henry and Anne’s relationship prior to their marriage is that it was one of equals. Henry respected Anne. He admired her intellect. He asked for her opinion. He followed her advice. Yes, he was king and she was courtier. Yes, there was a power imbalance. And perhaps she was playing a game. But their courtship was the most egalitarian relationship Henry ever had with a woman and when it soured, his rejection of her, her memory and their dynamic set the course for all the wives that came after.

Namely, Jane. In shunning what he actually desired he moved to what was safe – obedience, docility, dependence and placidity. His marriage to her was a reaction, but it was also going against the grain of his own temperament and his still lingering inclination to what we would today describe as “strong women” remained apparent.

Katherine Parr, his sixth wife, was highly intelligent and sought to influence him. It nearly cost her her life, but she tried her hand at it anyway. Marie of Guise, who went on to marry his nephew, James V of Scotland, was bandied about as a possible bride at one point and would have been a force at his court. His widowed daughter-in-law (via his illegitimate son, Henry Fitzroy) Mary Howard was yet another contender, but while her wit and mind may have drawn him in, he was wary of making another such woman his wife. (A relief to her, no doubt).

In short, he was attracted to what he grew to loathe. A challenge excited him, but at the end of the day he wanted to get his way. To put it bluntly, he liked being the prettiest girl at the party. His wives were ornaments to his own cult of personality. They were to be conquered and then changed from the sort of woman that enticed him to the sort of woman he saw himself married to – an updated version of his mother.

There is another thread that weaves its way through all six of Henry’s wives: virginity and/or female virtue. In seeking to divorce Katherine of Aragon he claimed that her marriage to Arthur had been consummated when she said it hadn’t. Anne Boleyn was charged with adultery and incest after playing the long game in refusing to sleep with him before marriage. Jane followed the same course, arguing she would enter her marriage a virgin. Anne of Cleves was considered repugnant on the grounds that her physicality indicated she wasn’t a virgin (more on that here). Katherine Howard was charged with lying about her virginity and adultery. Katherine Parr was safe because she was a widow; in that case her lack of virginity actually preserved her “virtue.”

So, what does this tell us? Well, to say Henry had a virgin/whore complex is putting it mildly and, again, that isn’t unique to him by any means, particularly in the 16th century. But, more precisely, what does this tell us about Henry viewed sexuality? Most men in his position, as his predecessors, peers and successors have shown us, would have passed their time with mistresses and worked something out re: the succession with a cousin or the existing Princess Mary.

Henry didn’t, but he also wasn’t a known philanderer. Yes, he took mistresses during his marriages to Katherine of Aragon and Anne Boleyn, but as far as we know, it was a modest number and they were relationships, not flings. Granted, there very well could have been shorter-term assignations to which we’re not privy, but the pattern that emerges is of Henry pursuing young, virginal girls and offering them love by way of the “respectable” position of his mistress. A mistress to whom he would be “faithful,” his marriage not withstanding.

He first approached Anne Boleyn in a similar manner. He offered her fidelity, love and respect, but not marriage. She, for whatever reason, demurred (more on that some other time.) It was this break in the pattern that set off all the rest. Her virginity and comparative youth promised fertility, a thing the King needed. Her intelligence, wit and personality made up the woman Henry wanted.

The problem with what Anne signified wasn’t just the unbelievable crash and burn of one of the most famous (if abusive) love stories in history, it’s that it created a tyrant. The Catholic Church was a good moderator of its Europeans monarchs and without its check Henry could pick up and put down lives as though they were chess pawns. Anne of Cleves and Katherine Howard were easy to discard. Katherine Parr very nearly met a similar fate, but had the good fortune to outlive him.

Which brings us to Katherine of Aragon and Jane Seymour, the two women who most closely fulfilled Henry’s ideal of “wife.” Katherine was married to Henry for 26 years, far outstripping her successors. For all practical purposes she was the true queen consort of his reign, her marriage a valuable alliance between England and Spain, her relations scattered about Europe. She was raised a princess and she knew what role was expected of her. She filled it well, save her ability to give Henry a son, and in the early years I believe that he loved her. She was no Anne Boleyn, but she was highly intelligent and strong and knew how to both lead and give way. She was the only wife Henry didn’t originally choose for himself and the only one who truly served him well.

What did her in were the usual, boring things: She aged and he fell in love with another woman.

As for Jane, hers is an incomplete story. We don’t know what would have happened had she lived. Yes, she gave Henry a son and that likely would have preserved her, but we can’t say that for certain because she was the only wife who did and she died so quickly afterwards. Her death mirrored Elizabeth’s 34 years before and Henry mourned her deeply – for her or what she represented is unclear. Perhaps, too, the deaths of all three of his wives – Katherine, Anne and Jane – hit him at the same time, whether he knew it or not (he likely didn’t). The magnitude of what he had done or, rather, undone causing a break between “king” and “man,” which he wasn’t able to articulate or address. Though, to reach the last point, one has to essentially project a thoroughly modern line of thinking, which causes problems.

So, what did Henry want from women? I think he wanted Anne Boleyn, but an Anne who could fulfill what she had promised him: a son. Her inability to do that as he broke from Rome, the Church to which he had once been intended and to which he was fervently devoted, caused a violent break. Her failure to keep up her end of the “bargain” made her a woman who had disappointed him, like a mother who died too soon or any other wife who failed to reflect what he needed her to – his virility, his chivalry and his superiority.

Had Anne given birth to a son in September 1533 (instead of the daughter who grew into Elizabeth I), I think it likely she would have survived. I reference that first pregnancy and not  her later ones, because I think the birth of a daughter in that moment, when he had been so sure it would be a boy, so confident in Anne’s ability to provide him with an heir, was in many ways the fatal blow to their relationship. After that, it was never quite the same; more precisely, he never saw her as the same. As with Jane, it’s impossible to say with certainty and, too, we can’t untangle what impact Henry’s increasing tyranny as the head of his own church would have had on their relationship, but that is my estimate.

Henry didn’t necessarily spend his life chasing down his mother, but her absence informed what he believed an ideal wife should be, even as his own fell short. Elizabeth of York lived and died in service to the Tudor succession. Ironically, so did all six of Henry’s wives.