Henry VIII and Anne of Cleves: “I Like Her Not”

The political marriage of Anne of Cleves and Henry VIII was short-lived, but Anne was the only one of Henry’s queens to live a comfortable life after her marriage.

Mar 15, 2024By Aloise Sauthier, BA with Honours in Art History and Visual Culture

anne of cleeves annulment henry viii


The marriage turned annulment of Anne of Cleves and Henry VIII has come to be known simply as the marriage that ended because Anne was too ugly for Henry. But this narrative cuts out a huge amount of detail, and the reality of the circumstances surrounding Anne and Henry’s brief marriage is much more complex than a simple lack of attraction.


The Engagement

The Family of Henry VIII, featuring Jane Seymour, by British School, 16th century, Source: The Royal Collection Trust


Anne of Cleves was to be the fourth wife of Henry VIII. While Henry was married to his third wife, Jane Seymour, the idea of a new bride wasn’t at all on his mind. Jane had been able to give him the greatest thing of all: A son. It is because of this that many believe Jane Seymour was Henry’s favorite wife.


Edward Tudor was born on the 12th of October 1537, and with his arrival, Jane made Henry’s dreams come true; finally, he had an heir to the throne of England. Sadly, this was not to be fairytale ending for the royal couple, as twelve days after Edward was born, Jane died due to complications from the birth. Henry was distraught; he was now, once again, without a queen — and he had only one male heir. Everyone knew that having only one son was not enough; a king needed an heir and a “spare” (Henry himself had been his father’s spare). Despite his grief, Henry needed a new queen who could give him another son.


Anne of Cleves was not Henry’s first choice for wife number four. Henry sent his court painter, Hans Holbein the Younger, across Europe to paint eligible princesses who had taken his fancy. One princess Henry set his sights on was Christina of Denmark. However, she was not in favor of the match, and reportedly said “If I had two heads, I would happily put one at the disposal of the King of England.” It seemed that Henry’s ease at beheading his former queen Anne Boleyn was frightening the princesses of Europe off, and with good reason. Despite Henry’s desires, it was advised by Thomas Wriothesley, the English diplomat in Brussels, that Henry should “fix his most noble stomach in some such other place.”

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Christina of Denmark, by Hans Holbein the Younger, 16th century, Source: The National Gallery, London


It was up to Thomas Cromwell, Henry’s chief minister and right-hand man, to turn the king’s mind — and heart — elsewhere. Cromwell’s search for a new queen of England had a pressing political motivation. Overseas, Holy Roman Emperor Charles V and Francis I of France seemed to be getting along better than usual, which was bad news for England. Cromwell knew England needed support in case the worst happened, and the new enemies-turned-allies Charles and Francis decided to wage war on England, their mutual enemy.


Thomas Cromwell sought out Protestant allies that could help England if they found themselves at war. This is where Cromwell came to suggest that Henry consider the daughters of the Duke of Cleves, Anne and Amelia. The Duke of Cleves was no stranger to feeling friction with Charles V, and their display of standing up to the Holy Roman Empire is what solidified them as a logical and strong alliance for England to have.


Flag and Coat of arms, Kleve Germany, Source: Wikimedia Commons


First, Henry sent over an ambassador to Germany to see Anne and her sister Amelia, and to discuss what the terms of a proposed marriage might be. The report from diplomat Christopher Mont was positive enough to convince Henry to send Holbein to paint the two daughters for Henry to see for himself what they looked like. It was not enough for him to hear others recount how beautiful the princesses were — Henry needed to make up his own mind.


Whether or not Cromwell had instructed Mont behind the king’s back to talk highly of the daughters’ beauty and promote the idea of an alliance with the Cleves family is debated — but is not an impossibility. Henry was presented with Holbein’s portraits and was totally enamored with Anne’s. No time was wasted, and plans for the marriage were set in motion. The final agreed-upon details were written up in a treaty, which was signed on October 4th, 1539.


Anne Arrives in England

Rochester Castle, by Bertram Nicholls, 19th century, Source: ArtUK.org


It was time for Anne to head to her new home, a strange, foreign land, with a language she did not speak. She had a long and tumultuous journey to England, but she finally arrived in Deal, Kent, on the 27th of December 1539. Anne journeyed through England towards London and was expecting to meet Henry on January 3rd. On January 1st, she was resting at Rochester Castle, when she received some unexpected visitors.


Henry had arrived early at Rochester Castle to surprise Anne. There was a chivalric tradition popular in elite circles where a princess has an unexpected meeting with a young man who she instantly falls in love with, only for her to discover later that he was really a prince in disguise — or in this case, a king. Henry appeared in Anne’s room, wearing a cloak and mask to disguise himself. Anne was alone, quietly looking out of her window, when suddenly Henry approached her and gave her a kiss.


Anne, who was not familiar with this tradition, did not realize it was really her betrothed in disguise. Naturally, she did not react well to the masked stranger kissing her in her room. She said nothing and turned away from her admirer in a state of embarrassment. Henry, who believed he was a handsome man, was mortified at Anne’s rejection. Did she not recognize a king when she saw one? Clearly, their love was not meant to be.


Henry hastily left to change into his regal attire and returned to Anne’s room. She recognized him this time and was respectful and courteous towards him. Unfortunately, the damage was done. Henry’s ego was hurt, and this couldn’t be undone. He left the room and is said to have proclaimed “I like her not.” 


Thomas Cromwell, after Hans Holbein the Younger, 17th-century copy of a 16th-century original, Source: The National Portrait Gallery


Henry pleaded with Thomas Cromwell to find a way out of the marriage. He tried to blame Anne’s appearance for his dissatisfaction, claiming she was “nothing as well as she was spoken of.” There is no record of anyone saying anything negative about Anne’s appearance prior to this, and Henry himself couldn’t deny she wasn’t that hideous, reportedly admitting she was “well and seemly.” It is most likely Henry was motivated by his own embarrassment, after the failure of their first meeting, to alter the narrative to frame Anne as the one who was undesirable.


The sensitive nature of the matter and its urgency placed a lot of pressure on Cromwell to get Henry out of the wedding. Unfortunately, there was no feasible solution to call off the marriage that wouldn’t subsequently offend Anne’s brother, the Duke of Jülich-Cleves-Berg, and inspire thoughts of retaliation through war — exactly what was being avoided with Anne and Henry’s wedding in the first place. Cromwell ran out of time and there was no way out, so the wedding went ahead as planned.


Henry and Anne were married on the 6th of January 1540 at the Royal Palace of Placentia in Greenwich. It is reported that Henry said to Cromwell on the way to the chapel “If it were not to satisfy the world and my realm, I would not do that I must do this day for none earthly thing.” As the day ended and the newlyweds retired to their bed chamber it all started to go very wrong very quickly.


Ditching Anne of Cleeves

Henry VIII, by Hans Holbein the Younger, 1540, Source: The Barbarini Gallery, Rome


Henry was very open in his retelling of events in the bedroom with his new queen. The problem was a lack of events occurring at all. Henry tried for several nights to consummate the marriage but to no avail. Again, the blame for this was placed entirely on Anne’s shoulders. Henry could not possibly be the reason for the lack of success, despite being twice Anne’s age and riddled with health problems that by this time were most likely causing unpleasant odors — it was all Anne’s fault.


The repeated attempts to try and make the marriage work with Anne eventually started to bore Henry, as it became plainly obvious this union was not one to last. Then, in March 1539, Anne received a new lady in her household named Catherine Howard. When Henry first set his eyes on her, the impetus to get rid of Anne gained a new momentum.


Henry was not discreet when it came to his feelings toward Catherine, and Anne herself was also noticing his clear attraction to her. His ministers knew that they needed to free him from his marriage to Anne as quickly and as gracefully as possible; Henry wasn’t one to wait patiently, and the longer he had to endure the situation the angrier he would get.


Portrait of a Young Woman believed to be Catherine Howard, 1540-45, Source the Metropolitan Museum of Art


Then, on the 24th of June 1540, Anne was sent to Richmond Palace in Surrey. Henry told her there were concerns about plague in the city, and it was recommended that she leave Westminster and retreat to the much more rural Richmond. There was promise of Henry joining Anne there soon after but the royal couple were not to see each other as husband and wife again.


Considering that we know Henry himself was terrified of illness, had there been any actual threat of plague, Henry would not have stayed in London as he did. Unsurprisingly, on the 6th of July, Anne was informed of Henry’s intentions to annul their marriage. Anne accepted the annulment without much fuss, which was the smartest thing she could have done. We can never know how Anne truly felt about Henry, and if she was more sad or relieved when their attempt at a marriage ended but the way she responded would ensure her safety and comfort for the rest of her life, which was a lot better than the fate of some of his other wives.


On the 12th of July 1540, the official announcement was made that the marriage of Anne of Cleves and Henry VIII had been annulled. Henry was not one to waste time, and was married to Catherine Howard on the 28th of July 1540.


As Anne was amenable during the annulment process, Henry was very generous and kind toward her in the years that followed, perhaps as a way of showing his gratitude for Anne’s acceptance of the annulment and making things a lot easier for him than they had been before.


Richmond Palace from across the Thames, c.1562, Source: The Ashmolean Museum


Anne received a lavish settlement that included Richmond Palace and Hever Castle — former residence of the Boleyns — as well as earning herself the moniker of the “King’s Beloved Sister.” She held rank above all the women in England, excluding Henry’s daughters and any future wives.


Considering the bitter ends that the rest of his wives met, Anne’s life was considerably better. She was often invited to court and maintained pleasant relations with Henry. The sad irony was that for Catherine Howard, her marriage to Henry very quickly deteriorated, and she became victim to Henry’s axe on February the 13th, 1541. Anne had successfully managed to survive her time with Henry VIII — a fate that Catherine, as well as Thomas Cromwell — could only have dreamed of.


Anne of Cleves by Hans Holbein the Younger, 1539, Source: the Louvre


Henry was not just going to let things go and move forward graciously from all that had happened. He had been poorly advised to pursue a marriage that ended up causing him a lot of stress and embarrassment, and someone had to pay the price for it, and it wasn’t long before the finger was pointing at Cromwell. As the feared alliance between Charles V and Francis I failed to materialize into anything worth worrying about, the reasoning for forming a protective alliance with Cleves that Cromwell had pushed on Henry had now become redundant. This made things much worse for Cromwell; he had put the king through a humiliating ordeal for a purpose that didn’t exist. It wasn’t helped that all of those involved in the marriage negotiations, including Thomas Wriothesley, saw Cromwell’s weakening status, and took their chance to absolve themselves of blame by using Cromwell as their scapegoat.


So, on the 10th of June 1540, Cromwell was arrested in Westminster. His execution was delayed by Henry until his annulment to Anne was complete, and after that, as we know, Henry wasn’t one to waste time. Cromwell was publicly executed on Tower Hill on the 28th of July 1540 — while Henry was happily enjoying his wedding day to Catherine Howard.


Anne of Cleeves’ Legacy

Anne of Cleves, by Bartholomaeus Bruyn the Elder, 16th century, Source: St. John’s College, Oxford


While history likes to remember Anne of Cleves as the “ugly wife,” there was much more to her than meets the eye. Probably the most successful bride of Henry’s, she was the longest surviving of all his wives and lived for 10 years after Henry’s death. She maintained favor with the Tudors and was even part of Mary I’s coronation procession alongside Princess Elizabeth in 1553. She slipped out of the limelight around 1554, after tensions arose surrounding the Wyatt rebellion but as her health started to decline, Mary I allowed her to stay at Chelsea Old Manor. It was here that she would later pass away on July 16th, 1557.


Despite her reduction over time to being known as the ugly fourth wife, Anne’s life and the complexities of her marriage to Henry VIII are these days being recognized with the interest and acknowledgment that they deserve. Anne of Cleves is recognized as a true survivor of the terrors of the reign of Henry VIII.

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By Aloise SauthierBA with Honours in Art History and Visual CultureAloïse comes from the seaside county of Cornwall. She has a BA in Art History and Visual Culture from the University of Exeter, where her interest in writing and research was ignited. Her topics of interest range anywhere from the Tudors to Tarot, and she has a constant desire to find out more.