After the death of Jane Seymour in 1537, Henry VIII was once again single and looking to mingle. But he was a man with a bit of reputation by then, and perhaps the daughters of England weren't in a hurry to roll those particular dice. Artist Hans Holbein was dispatched to Europe to paint the portraits of eligible royals and nobles for Henry's consideration. In the Duchy of Cleves (part of modern Germany), Henry found both his next bride and a Protestant ally against increasing pressure from a French-Spanish Catholic alliance.

But it's Henry VIII, so you know the relationship didn't go as was expected. Though Anne of Cleves came to England and was wed to the king, she committed a faux pas in their first bizarre meeting, which hurt Henry's feelings. Henry never recovered, the marriage was annulled after six months, but for whatever reason, the famously vengeful king gave his would-be wife an extremely generous settlement. Anne of Cleves, notably among Henry's wives, was able to live her best single life well into the reign of Queen Mary I.

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