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First Valentine Was Written From a Prison. History’s first valentine was written in perhaps one of the most unromantic places conceivable: a prison. Charles, Duke of Orleans wrote the love letter to his second wife at the age of 21 while captured at the Battle of Agincourt. As a prisoner for more than 20 years, he would never see his valentine’s reaction to the poem he penned to her in the early 15th century.

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