When Henry wanted to remarry after Jane Seymour, he sent his favored and well-respected painter Hans Holbein to travel to different courts of ladies he might marry to take their portrait. Holbein was considered well-able to paint portraits that represented the life-like image of the subject, and after a bit of trouble he was able to paint Anne. Holbein had been specifically instructed to make it as accurate as possible, but it wouldn’t do to insult the hosts by painting her poorly even if she were ugly, and there is a small argument that he gave her a strange look and expression to show that. Put a pin in that.

Moving on, Thomas Cromwell was especially eager for the marriage because he wanted an alliance that would aid them against Spain and France. The Duchy of Cleves was also a member of the Schmalkaldic League, which was an alliance of Protestant territories, and well-liked by Cromwell as a reformer. Henry would have been aware of those reasons, and considered them whether or not it was his first priority. He found Anne’s portrait to his liking and was eager for the marriage to commence.

Henry was a big fan of the ‘ideals’ of the day, including chivalric tradition and courtly love. Behind the saccharine poems, over-the-top gestures, jousting favors, sweet songs, gushy love letters, etc…was a long-standing tradition and set of etiquette for how to behave and court. Henry showed himself to be a man who could be very caught up in the fantasies of who he wanted to be and what he imagined his relationships with people were, as well as who he was to the people around him. So he got himself very worked up about Anne coming after the death of the wife who’d given him a son, and what a great love he’d have with this new, fetching bride.

The meeting of the King and his new bride was supposed to be a very planned affair and she was to have met him at Greenwich Palace in a formal reception.

Henry as part of his courtly love enjoyment was a fan of masques and roleplaying, he had surprised Catherine of Aragon during their marriage with a pretense of being Robin Hood. So Henry got it in his head that he would surprise Anne and she would immediately recognize him as her true love and it would be a big, wonderful thing. By that time he was around forty-eight years old, three-hundred pounds, had an oozing and ulcerous leg that smelled terribly, and Anne did not expect to see Henry where she stayed in Rochester.

Anne mostly spoke only German, her court wasn’t about the courtly love and dramatic romances, she had been educated to by a wife and house-manager. The showy displays of the English court would have been wildly foreign to her.

There are a few accounts from different men. One essentially said they had a lovely and sweet meeting filled with kisses and humility, another said that he found Anne not at all like her portrait and that Henry did also and was very uncomfortable being physical with her. But another has a more detailed account that tends to be regarded as correct.

Anne was sat by a window watching a spectacle outside when men with hooded cloaks came in. Henry went and embraced and kissed Anne and then presented her with a token from ‘the King’. She handled it politely but proceeded to more or less ignore Henry as he attempted to engage her. He left and returned in kingly attire and was announced for who he was, Anne realized [sort of] what had just happened and the two went off together and apparently had a sweet time despite the language barrier.

It’s speculated that Anne was, reasonably, mortified and confused and that her expression would have shown her disgust/upset/shock. The meeting was absolutely not what Henry envisioned. Henry was king, no matter how his body decayed the people of the court were supposed to pretend he was as pristine as the day he was coronated. But Anne had looked at him without that pretense, he had seen exactly the way an outsider saw him, and he didn’t like it all. Not to mention it ruined the whole idea of instant romantic connection and her just ‘knowing’ him as her love.

Although Henry was sweet to her face despite that, he made statements after like, ‘I like her not!’, and ‘I have not been well-handled!’. He felt, or said he felt, as though he’d been tricked into a marriage with someone totally unlike what he’d been described. Henry said that she was ugly, that she smelled, that her breasts were saggy such that he was sure she was no maid and that he couldn’t do his manly duty. But he assured his doctor it was her fault, not his, because he had had a nightly emission on his own.

During this, for different reasons depending on who is writing the account, Catherine Howard had become a member of Anne of Cleves’ household and Henry was besotted.

There are some speculations that Henry also decided he didn’t need the German alliance so much, certainly not more than he wanted a bride he liked better, but he also had planned at some point while trying to annul his marriage to Anne how to handle it. Henry eventually made Anne his ‘beloved sister’, granted her a bunch of benefits, gave her high court status, and said she could only keep it if she stayed in England. He also made her write to her brother and basically say that the marriage was out but the alliance was in.

Was Anne ugly and did Henry think so?

Holbein was an accomplished painter and he was never punished for the way he painted Anne. If the portrait were truly not a fair likeness, there should have been some reprimand. Also, Holbein himself would have known Henry wasn’t a king to cross with a false portrait, no matter how polite he had to be to the German court.

Although Anne didn’t ever claim to be prettier than Catherine Howard [that we know of], she was miffed when Henry married Katherine Parr and said he’d married someone ‘less pretty than herself’.

I forgot the position of the man off hand, he may be an ambassador, but the man said that Anne was of ‘middling’ beauty, which is also how he described Catherine Howard and seems to be his temperament.

Anne switched from German to English [or rather French] fashions during her attempts to fix the marriage with Henry and people found her surprisingly fair and noted that it did much to improve her appearance.

Going with the courtly love meeting, Henry had been perfectly content to embrace and kiss Anne and showed no signs of displeasure even when she was bundled up in conservative German fashion. And once the marriage was annulled, he stopped insulting her.

Rumors also sprang up later that he might remarry Anne, or that she'd had illegitimate children with Henry. If she were 'so ugly' or he'd kept speaking ill of her, then those rumors would have been less likely. Henry and Anne got on quite well after the annullment. Anne was also involved with Henry's own children.

Henry’s displeasure at the humiliating meeting, the fact that Anne had a language barrier and wasn’t someone he could discourse with intellectually as he liked, the fact she was not accustomed to the ways of his court, the fact that he found a way to keep the alliance without keeping her, and that he’d found Catherine Howard so desirable were the more likely causes of the break than that he simply thought she was ugly. Ultimately he may have, even if only because he convinced himself of that, but there was a lot that went into the split. Also, not all of his wives were considered very attractive even in their own time, and it’s noted that if Henry didn’t consider them ugly then it was odd to consider Anne so.