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Home Analysis of Works

Was Anne Boleyn the Wife King Henry Loved Most?

24bestpro by 24bestpro
July 6, 2025
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anne boleyn favorite wife king henry

Published: Jul 5, 2025written by Elizabeth Morgan, BA History w/ Tudor concentration

 

Lovers of British history are obsessed with Anne Boleyn. It is undoubtedly she, out of all the six wives of King Henry VIII, who is given the most attention in any publication or production.

 

Thanks to the enduring power of literature and media, Anne Boleyn has been reimagined as the most sensual and attractive of characters. Throughout the years since her death, she has been painted as an expert in the art of seduction; as an irresistible enchantress; as a woman of almost magical capabilities; and as the classic other woman.

 

Anne Boleyn may be the favorite Tudor queen among modern audiences but was she the favorite wife of King Henry?

 

Anne Boleyn: Wife Number Two 

anne boleyn holding rose
Portrait of Anne Boleyn, 1550. Source: The Tudor Travel Guide

 

“Divorced, beheaded, died; divorced, beheaded, survived.” 

 

We are all familiar with this catchy and meaningful jingle. Each of the six wives of King Henry VIII is represented by a single word; what took place before is forgotten, and their entire lives are summed up with only their ultimate fates.

 

Catherine of Aragon was divorced in 1533. Jane Seymour died in 1537. Anne of Cleves was also divorced but in 1540. Catherine Howard was beheaded in 1542. Catherine Parr survived when she saw the death of her husband in January 1547.

 

It is Anne Boleyn who is represented by the word beheaded the first time it appears in the poem. Yes, she was the first of King Henry’s wives to suffer trial and execution, when she experienced a swift downfall and disgrace in May of 1536 but what exactly led her to the lowest and most frightening point of her life? This unfortunate series of events is one that has been retold, time and time again, over the 500 years since her death.

 

henry vii van cleve
Portrait of King Henry VIII, by Joos Van Cleve, 1530-5. Source: The Royal Collection Trust

 

Of course, the first thing to know about Anne Boleyn is that she was the second wife and queen of King Henry VIII. It was Anne who replaced Catherine of Aragon — the Spanish princess who had fallen in love with King Henry over 20 years previously.

 

King Henry and Anne Boleyn’s romance lasted around ten years, their marriage just over three. A formal wedding took place on January 25, 1533, approximately four months after a secret wedding ceremony had been performed in November of the previous year. After this most special occasion, King Henry and Anne Boleyn were finally happy. After seven years of desperation, they were now able to be together, openly and honestly, as man and wife. How were they to know that their happiness would be short-lived? Their marriage was fleeting but intense. Their union brought great and unprecedented change in England and their relationship was woven with passion, strife, uncertainty, but most of all a life-altering form of love.

 

courting of anne boleyn
The Courtship of Anne Boleyn, by Emanuel Leutze, 1846. Source: The Smithsonian Museum

 

Despite the joy and relief their eventual wedding brought, their initial courtship was hardly as simple as it may seem to the untrained eye. The capturing of Anne Boleyn’s heart, and the tying of her hand to his, had been one of the most difficult challenges of King Henry’s life. One might say that he went through hell or high water to wed and bed her; the phrase would hardly be an understatement.

 

In order to please the woman he loved, King Henry divorced his loyal wife of 20 years, without so much as a kiss goodbye or a tear of remorse. As if to embarrass and dishonor her further, he had attended trial after trial in an attempt to prove that his marriage to her had not been valid in the first place. He had declared his previous marriage void, and in doing so willingly rendered his only living and legitimate heir a bastard. He rid himself of Cardinal Wolsey, his greatest friend and the most competent servant he had ever had. He had stripped Wolsey of his wealth and properties, changed them to suit Anne Boleyn’s liking, and handed them over to her as a thoughtful gift.

 

As if that were not enough, since divorce itself was not permitted by the Catholic Church, King Henry split both himself and his country from Rome, declaring himself Supreme Head of a new Church in England, and purposefully pushed his own soul toward supposed eternal damnation.

 

trial of catherine of aragon
The Trial of Catherine of Aragon, by Henry Nelson O’Neil, 19th century. Source: Wikimedia Commons

 

Surely, these points alone may seem proof enough of King Henry’s feelings toward Anne Boleyn. For what other reason would he have done all this, other than that he was madly in love with her? And, if we venture a little further through the story, we may ask ourselves another contrasting question. For what other reason would King Henry have sent her to her death? Was it life-changing love, or overwhelming hate, that inspired him to rid the world of the woman he had once adored?

 

To lead a king of England to voluntarily make these decisions, Anne Boleyn must certainly have possessed something very special, very unique, and very irresistible. She must surely have driven King Henry almost to insanity, whether it be with genuine love, passion, lust, desire, obsession, or possibly even a mixture of each.

 

As usual, to truly understand why King Henry felt as he did for Anne, we must understand the qualities of the woman herself. What better way to do that than by returning to the very beginning of her story?

 

Anne Boleyn: Birth, Childhood, and Early Life

thomas boleyn brass
Monumental brass in Hever Church in Kent to Thomas Boleyn, 1st Earl of Wiltshire, Anne Boleyn’s father, photo by J J Lincolne. Source: Flickr

 

Although there is no reliable record of her birth, Anne Boleyn is thought to have come into the world sometime during the late reign of King Henry VII. She may have been born anywhere between the years of 1501 and 1507.

 

Both Anne Boleyn and her two surviving siblings—Mary and George—took their first breath at their family residence of Blickling Hall in Norfolk. Mary was the eldest (born c. 1499), George was very possibly the middle child (c. 1504), and Anne the youngest (c. 1507).

 

Evidence of the assumptions regarding Anne Boleyn’s date of birth can be found within Blickling Hall itself. A statue and portrait of Anne may be found in the House. Both bear the inscription Anna Bolena hic nata 1507, which translates from Latin to English as “Anne Boleyn was born here in 1507.”

 

mary boleyn
Portrait of Mary Boleyn, by Remigius van Leemput, 1630-70. Source: The Royal Collection Trust

 

Nonetheless, the academic debate regarding the birth of Anne Boleyn continues among historians even to this day. The British historian Eric Ives publicly advocates for 1501, while the American scholar Retha Warnicke claims that it was more likely to have been 1507.

 

One thing we know for certain about Anne Boleyn is her parentage. Her father was Thomas Boleyn (an employee of Cardinal Wolsey and future English Ambassador to France). Her mother was his wife, Elizabeth Boleyn, formerly known as Elizabeth Howard.

 

Both the Howards and the Boleyns were recognized as influential families in England, but the Howards were a little more so than the Boleyns. When combined, the two resulted in the production of three extremely well-born sons and daughters. It has been argued that Anne Boleyn was of more noble birth than the majority of King Henry’s other wives. She was undoubtedly of a higher class than Jane Seymour, Catherine Parr, and Catherine Howard. However, she could not compete with the royal heights of Catherine of Aragon and Anne of Cleves.

 

Alongside the other two children in the Boleyn nursery, Anne Boleyn spent the early days of her childhood at Hever Castle in Kent. Initially, she received a typical education for a young girl of her standing. This included lessons in the genealogy of her own family, arithmetic, grammar, and British history.

 

hever castle
Hever Castle, Kent. Source: Wikimedia Commons

 

Anne Boleyn also successfully learned to read and write and developed many essential domestic skills such as dancing, embroidery, household management, music, needlework, and singing. She even learned how to partake in pursuits that would prepare her for a life at court. Firstly, she practiced games such as cards, chess, and dice. Secondly, she became proficient in sports such as archery, falconry, horseback riding, and hunting.

 

It was not until the year 1513 when she was aged between six and twelve, that Anne Boleyn left her family home to begin a new life abroad. Just like many rich young ladies of the era, Anne was sent by her father to spend some valuable time at one of the many royal courts in Europe. Having been accepted into the household of Margaret of Austria, Anne Boleyn took advantage of the position and remained there for two years.

 

To say that Anne Boleyn made a good impression would be an understatement. She impressed Margaret of Austria with her manners and willingness to learn. Margaret reported that Anne was “Well spoken and pleasant for her young age.” Margaret also remarked to Thomas Boleyn that Anne was “so presentable,” and declared that she was “more beholden to you for sending her to me, than you to me.” 

 

queen claude of france
Portrait of Queen Claude of France, by Jean Clouet, 1520. Source: Wikimedia Commons

 

A little later, thanks to her father’s charm and skills as a traveling ambassador in Europe, both Anne Boleyn and her sister Mary Boleyn were invited to join the service of Queen Claude of France. This was a coveted position; they were now a maid of Honor to the wife of King Francis I of France. Although Mary, for some unknown reason, was summoned home within the month, Anne did not return for seven years.

 

It was here, at one of the most fashionable and sought-after places in the world, that Anne Boleyn was molded into the woman with whom we are all so familiar.

 

To say that Anne Boleyn flourished in France would be an understatement. As well as serving Queen Claude efficiently, Anne also spent her time developing other lifelong interests in art, literature, poetry, and fashion.

 

Anne Boleyn also completed her studies of the native language, and could soon speak fluently and elegantly in perfect French. By the time she returned home to England nearly a decade later, she had blossomed into the finest example of a young, 16th-century woman: sophisticated, accomplished, fashionable, and desirable.

 

Anne Boleyn and King Henry VIII: Was It Love at First Sight?

daniel Maclise Henry VIIIs first interview Anne Boleyn
Henry VIII’s First Interview with Anne Boleyn, by Daniel Maclise, 1836. Source: Sotheby’s

 

By the time Anne Boleyn had arrived home in England in 1522, King Henry had occupied the throne for just over 13 years. He had been happily married to Catherine of Aragon—wife number one—for the entirety of his reign. The couple had one healthy child, the seven-year-old Princess Mary, who remained her father’s sole legitimate offspring. King Henry also had one illegitimate son, Henry Fitzroy, by Mistress Elizabeth Blount.

 

Although Catherine of Aragon was yet to produce a healthy Prince, it is unlikely that King Henry had yet seriously considered the idea of divorce. Although the question of his successor lay heavily on his mind, King Henry had many other thoughts with which to occupy himself. King Henry had only just entered his 30s. He was still good-looking, generally good-tempered, and athletic. His health was still adequate and he had yet to suffer any of the major injuries that would trouble him in later life.

 

Was he on the lookout for a new queen? Absolutely not. Was he waiting in anticipation of new mistresses and fleeting extra-marital affairs? Potentially, yes. Was he open to the idea of an intensely passionate seven-year romance? Well, obviously with the right woman, anything was possible.

 

henry ftzroy
Henry Fitzroy, 1533-4. Source: Google Art Project

 

Of course, it turns out that the right woman was just around the corner. Anne Boleyn was waiting, in a castle known as the Chateau De Vert, to be rescued by the strong and chivalrous King Henry — metaphorically speaking, at least. It is quite possible that one particular event changed both their lives forever.

 

On March 4, 1522, Anne Boleyn made her first recorded appearance at the royal court of England. This date just happened to be Shrove Tuesday, the day on which the Tudor population enjoyed many hours of feasting and merriment before entering the solemnity of Lent.

 

After a full day of jousting and a lavish banquet in the great hall of York Place, a pageant known as the Chateau De Vert was performed at the effort and expense of Chief Minister Cardinal Wolsey. The pageant had very little substance and instead was a shameless display of wealth. The whole event was designed to showcase just how much money and time was available to those taking part.

 

cardinal wolsey portrait
Portrait of Cardinal Wolsey, 1585-1596. Source: Art UK

 

The general idea of the pageant was that eight ladies were being kept prisoner in a castle known as the Chateau De Vert. The ladies were known collectively as the Graces and possessed individual names such as Beauty, Pity, Kindness, Constance, and Perseverance. The Graces were dressed beautifully in white satin, and each woman possessed a small mask to conceal their true identity.

 

The guards were another set of ladies, appropriately dressed in black satin, who bore names such as Strangeness, Unkindness, and Jealousy.

 

It is here, in a 16th-century casting list, that Anne Boleyn’s name appears for the first time in history. Hers falls neatly alongside some of the most prestigious names at the Tudor court. Anne (very appropriately) played Perseverance, one of the Graces.

 

Others taking part in the Chateau De Vert included King Henry’s sister Mary (Beauty), Jane Dormer (Constance), and Mary Boleyn (Kindness).

 

mary tudor and charles brandon
Wedding portrait of Mary Tudor and Charles Brandon, Duke and Duchess of Suffolk, by Jan Gossaert, c. 1515. Source: Wikimedia Commons

 

King Henry and his gentlemen, (including his friend the Duke of Suffolk), played the parts of Nobleness, Youth, and Liberty. They were to invade the Chateau De Vert and set the Graces free. Naturally, it was King Henry himself who was selected to play the part of Ardent Desire.

 

The chronicler Edward Hall (1496-1547), who appears to have been present at the pageant, gave a thorough description of what the Chateau De Vert might have looked like. “In the nether end of the same chamber was a castle, in which was a Principal Tower, and inside was a cresset burning and two other lesser towers stood on each side.”

 

After the appropriate signal—probably a noise replicating the firing of a canon—King Henry’s entourage of sword-wielding heroes charged at the castle.

 

Edward Hall records that after a long battle, “… at last the place was won.” He goes on to describe what happened next: “… then the Lord took the Ladies of honour as prisoners by the hands, and brought them down, and danced together very pleasantly, which much pleased the strangers, and all danced their fill.”

 

Could it have been that, in the midst of all this chaos, King Henry laid eyes on the mysterious, satin-draped Anne Boleyn for the first time in his life?

 

anne boleyn sketch
Portrait of Anne Boleyn, after Hans Holbein the Younger. Source: The Wellcome Collection

 

In the television series The Tudors, this scene portrays the moment at which King Henry and Anne Boleyn experience a slowed-down, once-in-a-lifetime, heart-stopping rush of love at first sight.

 

As they touch hands for the first time, as part of the rescue operation, King Henry in particular is overcome with the feeling that nothing in his life will ever be the same again. Recovering only a little, he then leads her onto the floor to dance. “What is your name?” he asks, mid-dance. She smiles meekly as she answers, introducing herself to both the King and the audience, “I’m Anne Boleyn.”

 

Little wonder King Henry fell in love with one of the actresses in the pageant — a roomful of white-satin-women to rescue must have been difficult for the young and chivalrous king to resist.

 

Although we all like to believe this romanticized version of events, it is equally as likely that King Henry began to notice Anne Boleyn’s presence much more gradually.

 

Anne Boleyn: Reasons to Support the Theory That She Was the Favorite

henry and anne boleyn hunting
King Henry and Anne Boleyn Deer Shooting in Windsor Forest, by William Powell Frith, 1903. Source: Wikimedia Commons

 

Now that we have reviewed Anne Boleyn’s early life, and rediscovered her first meeting and eventual marriage to King Henry, we may finally address the question of whether or not she could have been his favorite wife.

 

As you might already have guessed, there are many reasons to support the theory that Anne Boleyn was the woman he loved most — perhaps more convincing reasons than any of his other wives could scrape together.

 

The first reason to support the theory that Anne Boleyn was the love of her husband’s life was that—whether we like it or not—he pretty much proclaimed the fact himself. Between May 1527 and October 1528, King Henry composed and sent a series of love letters to his new sweetheart. These letters are passionate, intense, and borderline obsessive. To be fair to the king of England, he was nothing if not persistent.

 

Of course, as these were written during a condensed period of only around 18 months, they cannot be used as proof that he felt such strong emotion for any prolonged amount of time. However, when read one after another, no historian can be left in any doubt of the intensity of his feelings at the height of his longing.

 

henry viii hans holbein
Henry VIII, after Hans Holbein the Younger, 1537. Source: WGA

 

The last words of each letter reveal much of his devotion. On many occasions, he signs in varying romantic ways. “Written by the hand of him who is and always will be yours; written by the hand of your loyal servant and friend; written by the hand of him that longs to be yours; written by the hand of him that was, is, and ever shall be yours, by his own will.”

 

The whole collection is now owned by the Vatican Library.

 

Reason number two: Anne Boleyn got whatever she wanted, whenever she wanted it.

 

It may seem to the modern historian that Anne Boleyn could achieve whatever she desired with only the click of her fingers. This is because, to an extent, that is how it was. She had absolutely no doubt of how rich and powerful her husband was, and she had no qualms about taking advantage of that luxury.

 

hampton court palace photo
Hampton Court Palace, by KT Likes Coffee. Source: Unsplash

 

Anne Boleyn wanted to live at Hampton Court. Fine, Cardinal Wolsey would have to move out. Anne Boleyn wanted certain friends and advisors out of the picture. Okay, King Henry allowed himself to be forbidden contact with the chosen gentlemen. He even went so far as to send some into exile, or worse, to execution. Anne Boleyn wanted a royal wedding, a sensational coronation, and the title of queen of England. That could be arranged — even if she had to wait seven years for the pleasure.

 

As well as showering her with personal gifts and unthinkable privileges, King Henry went to extreme lengths to ensure that she was seen as superior to any other queen that England had yet known.

 

One example of this behavior can be found in the records of Anne Boleyn’s coronation. Unlike any other queen Consort, Anne Boleyn was crowned with Saint Edward’s Crown. This particular crown—named after Saint Edward the Confessor—had previously only been used to crown monarchs.

 

The historian Alice Hunt suggests that this was done to honor the child that Anne Boleyn was already carrying during the time of her coronation. This baby, who turned out to be the future Queen Elizabeth I, was originally assumed to have been a boy and the next king of England. However, it is entirely possible that Anne Boleyn wished to be crowned with the Saint Edward’s Crown herself, perhaps to make a point of receiving something better than her predecessor, Catherine of Aragon. Nonetheless, to make the strong point that Anne Boleyn was the most special of consorts, King Henry happily allowed her the privilege.

 

anne boleyn anonymous portrait
Portrait of Anne Boleyn, 1584-1603. Source: National Portrait Gallery, London

 

Reason number three: Anne Boleyn was not considered beautiful. Beauty has been used as a reason for us to believe that King Henry favored a particular wife, whether it be Catherine of Aragon, Jane Seymour, or Catherine Howard. King Henry famously enjoyed the company of beautiful women, and all these wives were notably attractive. However, the fact that Anne Boleyn was not considered particularly good-looking in her era tells us that she relied on much more than her appearance to attract a man.

 

Unlike the many other wives and mistresses of King Henry, it was not likely to have been her beauty that he initially fell for. Anne Boleyn was not pretty—at least not in the typical sense—but King Henry was driven mad with desire for her, nonetheless.

 

One of the most influential descriptions of Anne Boleyn was given by Nicholas Sander, around half a century after her death, in 1586. He claimed that Anne was “… of a rather tall stature, with black hair, and an oval face of sallow complexion.” He also described Anne as having “a projecting tooth under the upper lip,” although he also admitted that she was fairly “handsome to look at, with a pretty mouth.”

 

A slightly more reliable account of Anne Boleyn’s appearance comes from the Venetian diarist, Marino Sanuto, who made her acquaintance in Calais in October of 1532. He gave a more favorable, but not particularly flattering description. According to Sanuto, Anne was “not one of the handsomest women in the world, but of a middling stature, swarthy complexion, long neck, wide mouth, bosom not much raised.” On the other hand, he did admit that she possessed “eyes which were black and beautiful.”

 

anne boleyn coat of arms
Anne Boleyn’s Coat-of-Arms as Queen of England. Source: Wikimedia Commons

 

Despite a few positives that stand out among the insults, the general consensus seems to have been that she was not beautiful in comparison with the other ladies at the Tudor court.

 

Luckily, Anne had her charm, elegance, grace, intelligence, passion, sensuality, mental ability, vitality, and general attractive disposition to fall back on. It was probably these qualities, in place of her looks, that King Henry initially fell in love with.

 

Finally, reason number four: Anne Boleyn’s memory is permanently engraved into the walls of Hampton Court.

 

To celebrate his marriage to Anne Boleyn, King Henry instructed that his carpenters should engrave her personal coat of arms into the roof of Hampton Court’s Great Hall. He also desired that their entwined initials — a neatly joined pattern of H&A, should be added onto the wooden screens that border the same room. These reminders of King Henry’s love for Anne Boleyn can still be clearly viewed today.

 

Also featured on the roof is Anne Boleyn’s badge of the falcon, and the initials AR, standing for Anna Regina.

 

The fact that King Henry chose to mark his favorite palace with permanent reminders of his second wife makes two clear points. Firstly, he loved her; secondly, he intended that love to last a lifetime.

 

The Death and Legacy of Anne Boleyn 

anne boleyn in the tower
Anne Boleyn in the Tower, by Edouard Cibot, 1835. Source: Wikimedia Commons

 

It was on May 2, 1536, that Anne Boleyn’s removal as Queen of England truly began. She had been accused of treason in the form of adultery and therefore was arrested and installed in some private apartments at the Tower of London.

 

The unfortunate gentlemen who had been named as her lovers were Henry Norris, Francis Weston, William Brereton, the Court musician Mark Smeaton, and, perhaps most shockingly of all, her brother George Boleyn.

 

Just a few weeks later, on May 19th, Anne Boleyn received her ultimate punishment and was beheaded before a crowd at the Tower of London. When she appeared at eight o’clock in the morning, she was said to have been strangely calm, unexpectedly composed, and as dignified as a queen should be on any occasion. One eyewitness account tells us that she “… went to her execution with an untroubled countenance.”

 

Just a handful of people known to have been in the audience at this solemn event were Thomas Cromwell, Charles Brandon (Duke of Suffolk), the illegitimate Henry FitzRoy, and the Mayor of London.

 

She delivered her final speech as expertly as if she were talking not before a crowd awaiting her execution, but to a group of friends back home at Hampton Court. She finished with the words, “… and thus I take my leave of the world and of you all, and I heartily desire you all to pray for me.” Following that, she repeatedly uttered the words, “O Lord have mercy on me, to God I commend my soul,” as she was prepared for her death.

 

princess elizabeth
Portrait of a teenage Princess Elizabeth, future Queen Elizabeth I, by William Scrots, 1546-7. Source: RKD Images

 

The body of Anne Boleyn was buried in an unmarked grave in the Chapel of St Peter ad Vincula at the Tower of London. Over three centuries later, during the reign of Queen Victoria, Anne Boleyn’s skeleton was reportedly identified during renovations of 1876. Anne’s grave is now clearly marked on the marble floor. However, some historians believe the bones might have belonged to Anne’s cousin, Catherine Howard.

 

Anne Boleyn’s most important legacy is undoubtedly her daughter, Queen Elizabeth I, who reigned between 1558 and 1603 and is now remembered as one of the greatest monarchs England has ever known.

 

Anne Boleyn: The Wife King Henry Loved Most?

anne boleyn and percy
Anne Boleyn and Percy, by David Wilkie Wynfield, 1866, photo by Gandalf’s Gallery. Source: Flickr

 

So, was Anne Boleyn the wife King Henry loved most? Well, although history lovers may continue to speculate, and although academics may continue to debate, a definite conclusion will never be possible to achieve.

 

However, the majority of Tudor enthusiasts would agree that the first three of King Henry’s wives—Catherine of Aragon, Anne Boleyn, and Jane Seymour—would have a more realistic chance than the last.

 

Anne Boleyn was the wife with whom King Henry was most infatuated, for the longest period of time. Some respected historians even name Anne Boleyn as the first and only love of King Henry’s life.

 

Even if Anne Boleyn was not the favorite wife of King Henry VIII, it would certainly be difficult to argue with the idea that she is now the favorite queen of Tudor history lovers living today.



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