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History’s Oldest-Known Valentine Was Written in 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.

Valentine’s Day is the one holiday made for showing love and affection. But the history behind the oldest-known valentine involves a tale of royal in-fighting, warfare and imprisonment in a medieval tower.

The “valentine” itself was actually a few lines in a poem, written by Charles, the Duke of Orléans, in 1415, when he was 21 years old. Charles grew up in the fractious French royal family. As the nephew of King Charles VI of France, also known as Charles the Mad (who was believed to be schizophrenic), he was caught in the crossfire between his father, Louis I, who presided over the House of Orléans, and his uncle’s family, which oversaw the House of Burgundy, in their fight for control of France.

Like most royals of the time, Charles’s marital life was a matter of state, not heart. At age 12, he was married off to his 17-year-old cousin and daughter of King Charles VI, Isabella of Valois, already a widow after being first married at age six.

A year later, tragedy struck when Charles’s father Louis I, was assassinated, and his mother died soon after. Charles and his brothers vowed revenge on their first cousin John the Fearless, the Duke of Burgundy, whom they accused of murdering their father in a power grab, intensifying the family civil war.

The marriage of Charles of Orleans and Bonne of Armagnac at the Chateau de Dourdan, from The Book of Hours of the Duke of Berry . (Credit: Online Library of Liberty)

Charles’s young marriage to Isabella ended shortly after it began, when she died giving birth in 1409. The following year, Charles was wed in yet another political alliance—this time to 11-year-old Bonne of Armagnac, daughter of Bernard VII, Count of Armagnac and soon-to-be Constable of France. Their marriage solidified the union of the two bloodlines.

It also put the young duke in his father-in-law’s Armagnac camp in the years-long French civil war between the Armagnacs and the Burgundians. As battle after battle dragged on between the rival factions, Charles was captured and imprisoned by the Burgundians in 1415. While held prisoner in the Tower of London, he penned a poem to his wife the same year that he was captured at the Battle of Agincourt.

View of the tower where Charles was captured, illustrated in “Poems of Charles, Duke d’Orleans” c. 1500. (Credit: Apic/Getty Images)

In the poem, Charles uses the term “Valentine” referring to his wife, but his expression of love was more somber than the holiday greetings that we’re usually accustomed to. However, given the grim circumstances under which the letter was written, that’s no surprise.

My very gentle Valentine,

Since for me you were born too soon,

And I for you was born too late.

God forgives him who has estranged

Me from you for the whole year.

I am already sick of love,

My very gentle Valentine.

Having been imprisoned for 25 years, Charles was never able to see his wife’s reaction to the letter. She died sometime between 1430 and 1435, before reuniting with her husband or bearing any children.

One of the many letters written by Charles Duke of Orleans. (Credit: DeAgostini/Getty Images)

Beyond the Valentine he sent to Isabella, Charles wrote hundreds of other poems while in prison—many about love and nobility. But the longer he was in captivity, the darker his poetry became. His work is now available translated into English in several books, including “The Poems of Charles Orleans,” by Sally Purcell.

Years after Bonne’s death, Charles returned to France and was wed, at age 46, to Mary of Cleves, 14. They went on to have three children. He died in 1465.

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