Henry VIII
Marriage to Anne of Cleves

Having considered the matter, Cromwell suggested Anne, the 25-year-old sister of the Duke of Cleves, who was seen as an important ally in case of a Roman Catholic attack on England, for the Duke fell between Lutheranism and Catholicism. Other potential brides included Christina of Denmark, Anna of Lorraine, Louise of Guise and Amalia of Cleves. Hans Holbein the Younger was dispatched to Cleves to paint a portrait of Anne for the King. Despite speculation that Holbein painted her in an overly flattering light, it is more likely that the portrait was accurate; Holbein remained in favour at court. After seeing Holbein's portrait, and urged on by the complimentary description of Anne given by his courtiers, the 49-year-old King agreed to wed Anne.

When Henry met Anne, however, he was much displeased with her appearance. The King was reportedly taken aback and told his courtiers "I promise you, I see no such thing as hath been shown me of her, by pictures and report. I am ashamed that men have praised her as they have done, and I love her not!" Despite his protests, Henry knew that the situation was too far gone and he would have to wed his bride.

The marriage took place in January 1540, but it was never consummated. The morning after their wedding night, Henry complained about his new wife to Cromwell, stating:

"Surely, my lord, I liked her before not well, but now I like her much worse! She is nothing fair, and have very evil smells about her. I took her to be no maid by reason of the closeness of her breasts and other tokens, which, when I felt them, strake me so to the heart, that I had neither will nor courage to prove the rest. I can have none appetite for displeasant airs. I have left her as good a maid and I found her."

Henry wished to annul the marriage as soon as possible so he could marry another. Anne did not argue, and confirmed that the marriage had never been consummated. Anne's previous betrothal to Francis of Lorraine provided further grounds for the annulment. The marriage was subsequently dissolved in July 1540, and Anne received the title of "The King's Sister", two houses, and a generous allowance.
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