In the saga of King Henry VIII and his six wives, Anne of Cleves holds her secrets tight. She gave him no children, they were married for barely half a year, and most surprising of all, she survived. Legend has it that Henry fell in love with Anne’s flattering portrait, took one look at her in real life, and then promptly did the 16th-century version of “Swipe Left.” But was she as ugly as legend says? And what was the real truth behind Henry’s disgust? Read on to find out.
Anne of Cleves Facts
1. He’s No Pope of Mine
Anne of Cleves and her family were politically—and literally—in bed with the Protestant Revolution. Anne was born on September 22, 1515 in Düsseldorf (modern Germany) to the noble House of La Marck. Her father, John of Cleves, was part of the Schmalkaldic League, which was an alliance of princes against the Pope’s authority.
2. Friends With Benefits
Just totally coincidentally, Henry VIII was also opposing the Pope in his own country as Anne was growing up. Thus, he had reason—beyond Anne’s “beauty” or lack thereof—to enter into a marriage alliance with Cleves. Yeah, I know, we’re also shocked that this Henry VIII joint isn’t a timeless tale of love and romance.
3. The Lady Doth Not “Protest” Too Much
Despite her family’s Protestant sympathies, Anne was not deeply anchored to their faith. Instead, she was raised closely under the influence of her mother, Maria—a strict Catholic.
4. Sister, Sister
Though Anne’s tragic tale with the king has gone down in history, few people know the whole disturbing story of their courtship. For one, Henry didn’t just court Anne as his bride—he also considered her younger sister Amalia as his potential Wife #4. Maybe if he’d actually chosen Amalia, the disaster that was his fourth marriage never would have happened.
5. 16th-Century Tinder
In the late 1530s, Henry sent his favorite court painter Hans Holbein on a kind of creepy mission. He told him to go paint both Anne and Amalia and bring the paintings back to him so he could decide which one he liked best. Henry also insisted that Holbein paint the girls accurately and not try to flatter them, because he definitely didn’t want an uggo queen.
6. Face the Facts
When it came time to do portraits of the Cleves sisters, Hans Holbein ran into one big difficulty. Both Anne and Amalia kept their faces covered with veils, as per the modest German customs of the time. The painter had to wheedle his way in and gain their trust before Anne and her sister finally revealed their faces and let themselves be painted.
7. No Inheritance, No Husband
After Holbein returned and Henry saw both portraits of the women, he obviously went with Anne over Amalia—but not necessarily for warm and tender reasons. Many historians agree that the choice probably had less to do with looks, and more because as the younger daughter, Amalia had less hereditary rights than her sister. Aw, true love.
8. A Little Piece of History
Both Amalia’s portrait and Anne’s infamous painting survive in museums to this day.
9. Paint Me Like One of Your German Girls
Henry’s “don’t flatter them” directive to Holbein goes against the common wisdom that the painter deceived the king by painting a beautified portrait of the homely Anne. But hey, as anyone on Tinder will tell you, you don’t know you have chemistry with someone until they’re in the room. And let’s just say, when Anne walked in, Henry was not pleased….
10. The Real Thing Is Never as Good
Almost as soon as he met her, Henry complained about his wife-to-be’s looks. He was a little miffed at Holbein that she didn’t match her portrait, but he put most of the blame on someone else entirely. His chief minister Thomas Cromwell had urged him to marry Anne, and kept talking up her beauty. Henry was not happy she didn’t live up to Cromwell’s hype.
11. Swipe Left
Henry’s exact response after actually seeing Anne has gone down in history for his overwhelming distaste. He apparently grumbled, “She is nothing so fair as she hath been reported.”
12. Doing the Darn Thing
On January 6, 1540, Anne of Cleves married King Henry VIII at the Royal Palace of Placentia, despite all his protests and misgivings. On the day of the wedding, Henry gave his new queen a ring that he had inscribed with her new motto: “God send me well to keep.” It could have been a fairy tale day, but Anne’s nightmare was just beginning.
13. Bad Second Impression
After all, once the unhappy couple finally married, there was still the dreaded wedding night. Though it was a chance for Anne to rise in Henry’s estimation, it went horribly. On the morning after the wedding, the king reportedly complained, “I liked her before not well, but now I like her much worse.” So what actually happened? Well…
14. Kissing and Telling
When her ladies questioned Anne about her night with the king, Anne’s reply was revealing in all the wrong ways. She told them, “When he comes to bed he kisseth me, and he taketh me by the hand, and biddeth me ‘Good night, sweetheart’; and in the morning kisseth me and biddeth ‘Farewell, darling.'” So…just kisses then.
Did poor and sheltered Anne even know how to consummate her marriage? There is a fair chance that Anne believed these smooches were all it took to seal the deal.
15. Age Isn’t Always “Just” a Number
At the time of their marriage, Anne was literally half Henry’s age. She was just 24 years old; he was 48 and, by most accounts, looked like it hard.
16. Hot or Not
It’s the question we’re all here to learn: What did the legendary “ugly one” of Henry’s wives really look like? Was she really that ugly? Or was she secretly hot and just awkward? The answer probably lays in “attractive enough, I guess?” Though Anne was tall with pretty blonde hair, she also apparently had a “solemn face” that aged her beyond her 24 years.
17. Something’s off
It wasn’t just about looks; Henry accused Anne of even worse sins. He claimed that in addition to her plain face, she also had “very evil smells about her.” Oh, but then he really took it up a notch.
18. Fast and Loose
Henry didn’t only gripe about his plain new wife or her weird smells. He also threw her virginity into question, which was a serious allegation during a time when a woman’s worth was all about her “purity.” Henry’s evidence for this? “The looseness of her breasts and other tokens.” As you might tell from his way with words, Henry was a poet and songwriter in his youth.
19. Previous Engagements
After their disappointing meeting and wedding night, Henry was desperate to get rid of Anne. So he came up with an ingenious plot. In 1527, an 11-year-old Anne had been briefly betrothed to another man. Though her parents quickly cancelled the match, it would bite her in the well-clothed back in January, 1540.
20. Wife Strife
Henry’s councilors, looking for a way to weasel their king out of his ill-fated match, tried to use Anne’s childhood pre-contract to Francis of Lorraine as “proof” that she was not free to marry. Um, guys, we’ve all had exes. And maybe even this wasn’t enough, because they later took the divorce proceedings to a disgusting climax.
21. Not Hard to Believe
Henry held a full-blown trial for his divorce from Anne, and it was an absolute three-ring circus. You see, the king wanted to cut off the marriage on the grounds that they had never consummated the union—except he didn’t want anyone to think he was impotent or anything less than a macho man. To prove his vigor, he made an incredibly crude claim.
22. I Could If I Wanted
Get this: Henry hired a doctor to come in and defend his, er, male desires. According to the medic, His Majesty experienced an entire two “nocturnal pollutions” (i.e. wet dreams), even as he slept with Anne for days without consummating the marriage. In other words, the king was not impotent, it was only the marriage itself that was bad. He just needed you to know that.
23. It’s About Quality, Not Quantity
Anne and Henry were married for only six months—the briefest of his many marital adventures. They officially annulled their short and ugly union on July 9th, 1540. It only takes a little artistic license to assume that Anne was pretty relieved to leave the marriage with her head still squarely attached to her shoulders.
24. One Ring to Rule Them All
After the annulment was official, Henry and Anne had to go through the relatable awkward stage of giving their possessions back to each other. Anne’s wedding ring was one of the very first items to go, and she returned it in absolute style. When Anne sent it back, she told Henry to break it apart, since it was of little worth. Do I detect some shade?
25. Waste No Time
Even as he was married to Anne of Cleves, Henry committed a cold-hearted betrayal. Certain that Anne wasn’t The One, Henry started immediately casting about for his next wife. He quickly honed in on the young Catherine Howard, and married the new girl within a few weeks of his official annulment from Anne. Yep, sounds like Henry.
26. Ex Marks the Spot
In public, Anne held no hard feelings about Catherine Howard replacing her on the throne and in the royal marriage bed. For the New Year in 1541, Anne gifted her ex-husband and his wife two fine horses. She also joined the couple for dancing. Pretty cordial—but as we’ll see later, Anne’s reaction was much different when it came to Henry’s sixth wife.
27. Maybe Baby
Just because Anne was free of Henry doesn’t mean she was free of controversy, and soon a dark rumor started going around the castle. In November 1541, people started whispering that Anne of Cleves had given birth to a secret child. Just to thicken the plot, some sources even said it was King Henry VIII’s own son…
28. Don’t Say That About My Ex
Though the baby scandal was almost definitely a rumor gone wrong, the crown still took disturbing action. Henry launched a serious investigation into the whispers, and even detained two people for alleging that Anne was Henry’s true wife after all. Nothing turned up, thereby banishing this gossip to the trivia halls of history.
29. Someone’s Got to Pay for This Mess
Anne “survived” her term as Henry VIII’s fourth wife, but others suffered a much darker fate. Henry had Thomas Cromwell, the engineer behind the match in the first place, executed for treason on the same day he married his fifth wife, Catherine Howard. The man Anne had to thank for her crown lost his head on July 28th, 1540.
30. Red Tape Tragedy
The big question in all this is: Why the heck didn’t Henry get out while he still could? He was a super powerful King of England; surely he could snap his fingers and the wedding would be off? Well, it all goes back to the fact that Anne and Henry were a political match: There was simply no way to call the wedding off without offending his German allies.
31. School Doesn’t Prepare You for This
Anne had a perfectly functional education for a European princess. She was even innately clever enough to become fluent in English within a very short time. Unfortunately, however, her conservative family discouraged Anne from frivolities such as music, singing, and dancing. This was actually more of a problem than you might think.
32. Nothing in Common
Although Anne was accomplished in her own right, Henry was a lifelong geek of the arts—including all the things Mommy and Daddy Cleves forbid Anne from taking part in. So even if Anne could speak to the king in English, the pair probably had very little to actually talk about. Reminder, guys: emotional chemistry is just as important as physical chemistry.
33. The Greatest Escape
Henry proved to be a generous ex-husband to Anne of Cleves, even though most of his ex-wives couldn’t say the same. After she agreed to the annulment, Henry hooked Anne up with a severance package that included great manors, estates, and a sexy royal income. Not bad to keep your head and your financial independence.
34. Sister From a Different Mister
After their divorce, Henry kept the random acts of kindness rolling. He ruled that Anne would be England’s highest-ranking lady, with only the King’s wife and daughters ahead of her in precedence. He even adopted her in name as “the King’s Beloved Sister.” Did that make up for all the torment he must have put her through? Gonna go with “no.”
35. I’m a Cool Stepmom
Anne got along with all of Henry’s kids. She even sent gifts to the king’s heir, the future Edward VI, which indicated a friendly relationship, and was close with the future Queen Mary I. She also made an impression on the future Elizabeth I; when Anne passed on, she left her younger stepdaughter the “second best” jewel in her collection. Noice.
36. Say Neigh to This Name
Anne’s oft-repeated and cruel nickname, “The Flanders Mare,” did not originate from Henry. In fact, it didn’t even originate from the Tudor period! The name only emerged in the late 17th century, when the history of Henry VIII grew into legend. Anne was luckily spared the hurtful moniker during her lifetime.
37. Hitting Her 40s Hard
Anne’s later life was the picture of idyllic living in many ways. For a time, she enjoyed good favor in court under Henry’s daughter Queen Mary I, and eventually retired to a quiet life away from court. According to one source, the middle-aged Anne was “courteous, gentle, a good housekeeper” and generous to all her servants.
38. Switching Sides
Anne had to make more than a few trade-offs when she married Henry VIII. For one, he expected her to convert to Anglicanism when she married him, and Anne obediently agreed.
39. Game Recognize Game
Anne was so close to Queen Mary, she likely even attended the monarch’s coronation at Westminster Abbey, and she even converted back to Roman Catholicism for the Catholic queen.
40. Fresh Fruit From the Family Tree
Even from her far away homeland, Anne was a distant cousin to Henry VIII. Like all his wives, Anne of Cleves is a descendant of King Edward I “Longshanks” of England. Yep, King Henry sure did have a type when it came to his wives. Edward was Anne’s nine-times great-grandfather, for those who care to keep exact count.
41. The Last Laugh
Anne is the longest surviving of Henry’s wives; she outlived not only the other queens, but also the king himself. On July 16, 1557, just months shy of her 42nd birthday, she passed on in her adopted country of England, mostly likely from cancer. When the former queen died, her family gave her a heartbreaking tribute.
As Queen Mary I’s beloved “aunt,” Anne of Cleves was buried in the legendary Westminster Abbey, albeit not in a very prominent place. Despite her annulment, her grave reads “Anne of Cleves, Queen of England.” Even more impressive? Anne of Cleves is the only one of Henry’s wives to be buried in the hallowed Abbey.
43. Petty Theft
In 1542, Anne found herself in hot water with King Henry VIII all over again. By then, the king believed Queen Catherine Howard had been unfaithful to him, and the poor girl was awaiting execution for treason. Not content to suffer through yet another of his breakups on his own, Henry lashed out at Anne instead.
The hurting Henry sent Anne a terse letter, ordering his adopted sister/ex-wife to return a royal ring, which Catherine had given to Anne as a gift. Way to strike at two exes in one swoop. But the mess was just getting started…
44. Never Settle for Less Than Me
History has tended to paint Anne as a humble and shy woman, but the truth is much different. When Henry executed his fifth queen Catherine Howard in 1542, Anne harbored a dark secret. There are hints that she held some hope of becoming queen again, with her brother even trying to pressure Henry into taking her back. Instead, it all kind of blew up in Anne’s face.
45. Age Before Beauty
Just when Anne thought her time had finally come as the permanent Queen of England, Henry went and chose Catherine Parr as his sixth wife. But that wasn’t even the worst part. Parr was an English widow who was actually a few years older than Anne of Cleves. Ouch, that’s one’s gotta hurt…and Anne did not take the news well.
46. A Great Burden
We don’t know how exactly Anne reacted to Catherine Howard’s execution, but she reportedly detested the idea of the upstart Parr as her replacement. I mean, Anne did think of herself as the more attractive option, but she also remarked, “Miss Parr is taking a great burden on herself.” Is it just me or does that sound like more of a swipe at Henry?
47. Mystery Man
Anne is now infamous as Henry’s rejected queen, but modern historians suggest a more disturbing reason for his disgust. Anne’s first meeting with Henry was a diplomatic blunder: Making their way to London, Anne’s party stopped on New Year’s Day 1540 at Rochester, where she took time to look at bull-baiting from the window. Suddenly, an old burly stranger entered the room—and everything went horribly wrong.
48. Love Is Blind
You see, this stranger was really Henry VIII in disguise. He had wanted to creep in and get a sneak peek of his new bride-to-be. He also expected that she would see through his costume via the power of “true love”…or something. Spoiler: This was not a good idea. When he approached Anne, her response made his blood run cold.
49. Why Don’t You Understand My Cosplay?
Depending on the account, either Henry tried to get Anne’s attention and was politely ignored, or he outright tried to kiss and grope her, which understandably caused the young woman to ring the alarms about a strange dude harassing her. Either way, it was utterly disastrous, and Henry left the encounter angry, embarrassed, and possibly ready to take revenge…
50. You Don’t Fire Me, I Quit
Some modern historians believe that this ill-fated early encounter between Anne of Cleves and Henry VIII sealed her fate. According to them, Anne’s lack of enthusiasm for Henry (even in disguise) made the king put up his defenses. If she was unimpressed with him, he may have decided to be unimpressed with her no matter what. And the rest, as they say, is history.