It took a few years for King Henry to recover enough from Jane's death to consider marriage again. This time it seems he chose to go back to tradition and he looked a Germanic alliance. Anne of Cleves was suggested and a portrait of her was sent for his assessment. Content with what he saw in the portrait he agreed to the marriage.
Anne of Cleves
Upon meeting Anne in person Henry found her unattractive and endeavored to see if the marriage could be avoided, but it would have been impossible without causing offense. The marriage went ahead and lasted for six months before Henry requested an annulment of the on the grounds that it was never consummated.
Anne complied gracefully with his wishes requesting only to be able to stay in England in order to avoid further political marriages and to continue to be able to have contact with the royal children with whom she’d formed strong bonds. Henry granted this and much more. She received a princely income, several properties and he bestowed the honorary title of “The King’s Beloved Sister” upon her. They developed a close friendship and it seems she went on to have a content, happy life.
Back to his old ways almost as soon as he and Anne were married, Henry was lusting after a lady in waiting to his wife again and this time it was Anne Boleyn’s cousin, Catherine Howard. Almost as soon as the marriage to Anne was annulled, Henry married Catherine. By now, of course, Henry was getting rather old (nearly 50) and Catherine was a young, attractive, spirited teenager. Like her cousin before her she ended up on trial for adultery and therefore treason, which ended in the same fateful walk to her execution by beheading. This time, as much as Henry didn't want to believe it, the accusations of adultery were true and to top it off she it was revealed that she wasn't even a virgin when they married.
Furious at being cuckolded by Catherine Howard, Henry put in place a ruling that anyone with any knowledge that any possible new suitor might not be chaste or a virgin had to reveal it under threat of death. This put the fear into everyone as to Henry's next choice for marriage, because how can anyone be certain of the virginity of a lady? So when the twice widowed Catherine Parr caught his attention a collective sigh of relief might very well have gone through court. There was obviously going to be no attempts at pretense of her being a virgin.
Catherine was intelligent, very well educated and had been a devoted step mother to her previous husband's children. Despite having hopes to marry Thomas Seymour, brother of the late Jane Seymour, she dutifully accepted Henry's marriage request. During her time with Henry she managed to talk him into instating his daughters, Mary and Elizabeth, as royal heirs and was very capable as regent when Henry went away on campaign.
Upon his death Henry returned to Jane Seymour's side and they were buried together. Catherine went on to marry Thomas Seymour, the only husband she chose herself, but died shortly after childbirth.
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