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The ancient Roman festival Lupercalia took place annually on February 15 and involved primitive forms of courtship and matchmaking.
St. Valentine was also executed on February 14, around 278 A.D. Legend has it that he befriended the jailer's daughter and wrote a letter to her the night before his execution, then signed it, "From Your Valentine."
Two centuries later, Pope Gelasius ordered that Lupercalia be replaced with February 14, observing St.Valentine's Day.
The Romans also constructed the idea of Cupid, a god of love, which was adapted from Eros, a Greek god of passion and fertility.
Valentine's Day first became romanticiced by classic authors.
Chaucer (1300s)
Chaucer's epic poem The Parliament of Fowls referenced "Seynt Valentynes day."
Shakespeare (16th century)
Shakespeare popularised love with his "Sonnet 18" "Shall I compare thee to a summer's day?" In Hamlet, the character Ophelia recites a song about a young lady's experience with the holiday, "Tomorrow is Saint Valentine's day," and "To be your Valentine."
By the 1700s, Valentine's Day made its way to the United States. It became traditional for friends and lovers of all social classes to exchange small tokens of affection or handwritten notes. In England, the Industrial Revolution eventually included the production of fancy valentines.
When American Esther Howland received her first English valentine greeting in 1847, she believed there would be an American market for these formal, English-style greetings. She created the earliest American Valentine's Day greeting cards.