Jane Seymour and Anne Boleyn: Two women, Two queens, One path twice trod

Jane Seymour © Hans Holbein the Younger – The National Portrait Gallery

(© Unknown Artist – The National Portrait Gallery)

In the glittering but perilous court of Henry VIII, few stories are as captivating or as tragic as those of Anne Boleyn and Jane Seymour. Their story is not one of friendship or rivalry in the traditional sense, but of two women unknowingly cast as foils to one another in the grand drama of court and the grand drama of the King Henry VIII himself. They were not enemies in the way popular history sometimes imagines or paints them to be in the dramatizations of their stories, but nor were they allies. Instead, they were successive bearers of the impossible burden of queenship in an era where a woman’s value was tied to her ability to produce a male heir — and to please a king whose favour could shift like the English weather. Anne; clever, famously witty, and charismatic, with bold opinions and even bolder ambitions, revolutionised the precedents of what a queen could be and where she could come from. Jane; renowned as ever gentle and dutiful in the eyes of many, appeared to restore a more traditional femininity to the throne after Anne's stormy and tumultuous reign. But one made way for the other, and tied them together in ways history would forever remember.

Yet, it is too simple to say that Anne was the fire and Jane the calm after the storm. Their stories reveal deeper complexities. Consider agency and manipulation, love and survival, and women navigating a world not made for them. Anne’s rise was magnificent, but her fall, brutal. She captured the king’s attention and kept it longer than most, changing the course of English history as catalyst to the English Reformation, and ultimately losing her life for it. Jane, in contrast, was crowned queen in the shadow of Anne’s execution. Her reward was not a tragic downfall but a tragic end of another kind: death shortly after giving birth to the long-awaited male heir, Edward VI. Their lives, so closely linked through Henry’s obsession, unfolded like twin arcs, parallel yet opposite. Anne fought fiercely and lost all; Jane complied quietly and died in triumph. Their legacies have been filtered through centuries of myth-making and moral judgment, but behind the crown, the court, and the king, they were women with hopes, fears, and dreams, women whose choices were constrained and whose lives were shaped not just by ambition, but by the perilous game of Tudor politics – and men.

This blog post will delve into the intertwined stories of Anne Boleyn and Jane Seymour, considering their relationship with each other, as women bound by fate, caught in the dangerous dance of power, and remembered by history in starkly different lights.

Anne’s path to Queenship and her only mistake:

The two women’s path to queenship was not wholly dissimilar. Both were ladies in waiting to their queen, under oath to act with demurity and discretion, each violating that oath to become the obsession of the King. But Anne’s journey to queenship was undoubtably longer, 6 years in total when we consider the year of the proposal, 1527, to the year of her marriage and crowning in 1533. As a result, it was more perilous and put her in a much more vulnerable position when she could not uphold her end of the bargain to produce a male heir.

The Chateau Vert Pageant, held on Shrovetide of 1522, is where this blog post will consider Anne’s path to queenship beginning. Tudor enthusiasts, and more specifically Boleyn fans, regard this event with the upmost significance, as it was Anne’s debut at the English court after having returned home from France, and is the first circumstance that can place both Henry and Anne in the same room together, for the first time, with 100% certainty.

Her courtship with Henry VIII began sometime after this, with rumours quickly swirling that Anne Boleyn, the quick-witted, ‘French-woman-born’ and captivating lady-in-waiting to Queen Catherine of Aragon, had caught the eye of the king. Some whispered that Henry’s interest in Anne ignited during court masques and dances such as this one, while others claimed it began in earnest when he tired of her sister Mary, who had already been his mistress and bore (potentially) two of his bastard children.

Whatever their beginning, their courtship is perhaps most vividly captured in Henry’s surviving love letters to Anne, 17 in all, which give a rare glimpse into the heart of a king who was both infatuated and frustrated. In them, he longs to kiss Anne, as well as her “pretty duckies”, signs off as “your loyal servant” and professes deep longing, pledging fidelity and devotion, even going as far to draw their initials beside each other in a heart. These letters reveal Henry’s growing obsession and Anne’s ability to maintain both distance and allure. It was clear Anne would not be his mistress in the traditional sense. She had her sights set higher. And higher she would climb. By Christmas 1527, Anne accepted Henry’s proposal of marriage, though they would remain publicly unwed for several more very public years. And behind her, undoubtedly, stood the men of her family, her father, Thomas Boleyn, and her uncle, Thomas Howard, Duke of Norfolk, who saw in Anne a vehicle for the Boleyn rise. Their encouragement, whether direct or subtle, shaped Anne’s resolve and fortified her position at court. Throughout the late 1520s and early 1530s, Anne was treated as a queen in all but name. She had her own lodgings, her own attendants, and received honours typically reserved for royalty. When she appeared at court, all eyes were on her, and her influence grew daily. At Greenwich, she even held her own court at Christmas and New Year’s with Catherine long since sent away to the country, for appearances sake. Anne was Queen in all but name.

Jane’s blueprint to queenship:

But Anne did one thing that would set about her own doom, and make way for Jane. During the late 1520s, during the height of their courtship, Anne is believed to have introduced Henry to the writings of William Tyndale, particularly his English translation of the Bible and his book The Obedience of a Christian Man. Tyndale’s works were banned in England, branded heretical by the Catholic Church, yet Anne owned copies and kept them in her personal library. She reportedly gave Henry a copy of The Obedience, a book that argued kings were accountable only to God and not to the Pope. As a result, she was beloved and hated in equal measure, both at court and among the English people, splitting the country in half, protestant and catholic.

To Henry though, Tyndale’s ideas were a revelation. Here was the theological justification for breaking from Rome, for rejecting the Pope’s authority, and for becoming the supreme head of both state and church, securing Anne as his wife and absolute authority in his kingdom. Anne hadn’t just handed him a religious text—she had handed him a blueprint for absolute power. This idea became the ideological foundation for England’s split from the Catholic Church and the formation of the Church of England. For Anne, it was a political masterstroke that handed her this long-awaited marriage, and queenship. But it came at a steep cost.

First, it earned her the deep and lasting hatred of Catholic traditionalists (Seymour’s included), both within the court and among the people. She was seen as a heretic, a Jezebel who had poisoned the king’s soul and led the nation astray. But perhaps more critically, in awakening Henry to the intoxicating idea of unchecked authority, Anne had inadvertently created the very conditions that would later doom her. She had taught Henry how to rule without limits—and how to suspect those closest to him. Power and paranoia became his ruling principles, and once Anne could no longer provide what he wanted most - a male heir - she, too, became disposable.

Enter Jane:

Jane Seymour’s path to queenship was quieter than Anne Boleyn’s, but no less calculated or significant. Born into a respectable but not especially powerful noble family, Jane entered court life as a lady-in-waiting to Queen Catherine of Aragon around 1529. There, she served alongside Anne Boleyn, who was still rising in the king’s favour. Jane would later serve Anne again, this time as queen, following Anne’s marriage to Henry in 1533. This proximity to two queens gave Jane a front-row seat to the mechanics of power, the volatility of Henry’s affections, and, crucially, the lessons Anne’s rise and fall would offer.

It was in the summer of 1535, during Henry’s royal progress through the West Country, that his attention seems to have turned toward Jane. The court stayed at Wolfhall, the Seymour family seat in Wiltshire, and it’s here that their relationship likely began to blossom. Jane, now in her mid-20s and unmarried, stood out not for her wit or glamour like Anne, but for her quiet demeanour, her modesty, and her reputation for virtue. She was, in many ways, the opposite of the woman who currently wore the crown.

When Henry began to pursue Jane more seriously, likely proposing she become his mistress, she refused him. She is said to have presented him with a letter, or possibly a token, declaring that her honour could only be surrendered in marriage. This move - so familiar - was not accidental. Jane had learned from Anne. Anne had rewritten the rules of courtly flirtation, having famously refused to become Henry’s mistress and instead maneuverer herself toward the throne. Jane, whether on her own or with the guidance of her ambitious family, used that same strategy. Anne, perhaps unknowingly, had taught the women of court how to captivate Henry, not with surrender, but with refusal.

Jane’s soft manner and perceived innocence made her the perfect contrast to Anne, whose assertiveness, temper and sharp tongue were beginning to wear on Henry. By early 1536, Anne had miscarried a son and lost her last bit of security. Jane, meanwhile, was rising. Less than 24 hours after Anne’s famous execution in May 1536, Jane was betrothed to Henry. Ten days later, she was his queen. Her quiet patience and calculated virtue had carried her to the highest position in the realm—proving that sometimes, the most powerful moves are made in silence.

But what to we know about their (short) time together?

The relationship between Anne Boleyn and Jane Seymour is largely shrouded in mystery, but the fragments we do have suggest it was defined by tension, rivalry, and cold politeness—rather than outright confrontation or intimacy. Most of what we "know" is inferred through the context of court politics, recorded observations from ambassadors, and the few personal interactions noted in contemporary sources. One famous, possibly apocryphal, exchange between Anne and Jane was reported after Anne supposedly found Jane receiving a gift from the king. Anne, furious, is said to have torn the gift from Jane's hands and berated her. Whether true or not, the tale reflects the widely accepted narrative of a simmering tension between them.

Unlike other court rivalries, there is no suggestion that Anne and Jane ever reached any sort of personal understanding. After Anne’s arrest, trial, and execution, Jane made no public comments about her predecessor, and there was no effort at posthumous reconciliation or tribute. In short, their relationship was shaped more by their positions and the politics around them than by personal connection. They were symbols of a succession crisis, pawns and players in a deadly game, each standing in the shadow of the other at different points in their rise.

Two women, Two queens, One path twice trod.

What we do know though, is that Anne undoubtedly set the stage for Jane, doing the dirty and dangerous work of creating the blueprint for how to captivate a king, displace a queen, and rise to power in a court governed by male ambition and royal whim. Anne’s careful navigation of Henry’s courtship, her calculated refusals, her resistance to becoming merely a mistress demonstrated to everyone, including Jane Seymour and her politically astute family, exactly how a woman could leverage virtue, timing, and royal desire into queenship. It is a tragic irony that in her own creation, Anne also created the conditions for her downfall. She taught Henry to defy the Pope, to bend the law, to follow his heart rather than duty, all of which he would later use to discard her, just as he had discarded Catherine of Aragon. She taught him how to take what he wanted, and how to justify it. And when Anne could no longer provide the male heir he craved, he used those very lessons against her.

Without Anne’s example, Jane could not have soared to the heights she did. Anne had already broken the boundaries, already shown that a queen could be replaced, and not quietly or shamefully, but with a grand narrative of love and destiny. In doing so, she paved the way for Jane’s quiet ascent. Jane did not need to be fiery or controversial; Anne had already been that. Jane only needed to be the opposite.

Though we know little about the personal relationship between Anne and Jane, what is clear is that Anne’s example loomed large. She had rewritten the rules of court life, showing how far a woman could rise if she was clever enough to understand the king’s moods, and bold enough to challenge his expectations. Whether Jane herself fully grasped this, or whether it was her family who studied Anne’s rise and used it as a manual for their own advancement, the end result was the same: Jane followed in Anne’s footsteps almost exactly, and then walked over her dead, cold body into her (still warm) shoes as queen. Without one, the other could not have risen. Their stories are not merely connected - they are dependent on each other, two halves of a single, dangerous legacy.

Resources:

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14. Bordo, Susan. The Creation of Anne Boleyn: A New Look at England’s Most Notorious Queen. Boston: Houghton Mifflin Harcourt, 2013.

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