(6 January 1540 - 9 July 1540) (annulled)
Henry wished to marry once again to ensure the succession. Thomas Cromwell, created Earl of Essex, suggested Anne, the sister of the Protestant Duke of Cleves, who was seen as an important ally in case of a Roman Catholic attack on England.
The king agreed to wed Anne. On Anne's arrival in England, Henry is said to have found her unattractive, privately calling her a "Flanders Mare". Although other people have thought to have found her rather pretty.
Negotiations with Cleves were in full swing by March 1539. Cromwell oversaw the talks, and a marriage treaty was signed on 4 October of that year.
Henry valued education and cultural sophistication in women, but Anne lacked these: she had received no formal education but was skilled in needlework and liked playing card games. She could read and write, but only in German. Nevertheless, Anne was considered gentle, virtuous, and docile, qualities that made her a suitable candidate for Henry.
Anne was described by the French ambassador, Charles de Marillac, as tall and slim, "of middling beauty, and of very assured and resolute countenance". She was fair haired and is often said to have had a lovely face. She appeared rather solemn by English standards, and looked old for her age. Holbein painted her with high forehead, heavy-lidded eyes and a pointed chin.
Henry first went to meet her at Rochester on her journey from Dover. According to the sworn testimony of his companions, he was promptly disappointed with her appearance, although there are many documents from the time which describe how Henry and some of his courtiers sneaked into the room where Anne was watching bull-fighting, wearing masks and cloaks, when Henry boldly kissed her. Henry, being of tall stature and well-built in his youth, had been instantly recognised by his past wives when acting out this courtly-love tradition, although Anne had never met her husband-to-be before, and pushed him away startled, cursing in German. Henry did then reveal his true identity to Anne, although he is said to have been put off the marriage from then on. Most historians believe that he later used her 'bad' appearance and incapability in bed as excuses, saying how he felt he had been misled, for everyone had praised Anne's attractions: "She is nothing so fair as she hath been reported," he complained. Henry urged Cromwell to find a legal way to avoid the marriage but, by this point, doing so was impossible without endangering the vital alliance with the Germans.
Despite Henry's very vocal misgivings, the two were married on 6 January 1540 at the royal Palace of Placentia in Greenwich, London by Archbishop Thomas Cranmer. The phrase "God send me well to keep" was engraved around Anne’s wedding ring. Immediately after arriving in England, Anne conformed to the Anglican form of worship, which Henry expected. The couple's first night as husband and wife was not a happy one. Henry confided to Cromwell that he had not consummated the marriage, saying, "I liked her before not well, but now I like her much worse".
Anne was commanded to leave the Court on 24 June, and on 6 July she was informed of her husband's decision to reconsider the marriage. Witness statements were taken from a number of courtiers and two physicians which register the king's disappointment at her appearance. Henry had also commented to Thomas Heneage and Anthony Denny that he could not believe she was a virgin. Shortly afterwards, Anne was asked for her consent to an annulment, to which she agreed. The marriage was annulled on 9 July 1540.