The History and Evolution of Valentine's Day
TLDR Valentine's Day originated as a Christian feast day for St. Valentine, but its association with love and romance began in the 15th century. The tradition of giving Valentine's cards started as love letters and eventually evolved into the modern greeting card industry, with over 20 billion dollars being spent on Valentine's Day in the United States alone.
Timestamped Summary
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Valentine's Day has its roots as the Christian feast day of St. Valentine, but there isn't much known about him or whether there were multiple St. Valentines.
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Valentine's Day was originally a feast day for a saint, but some researchers have tried to link it to the Roman Festival of Lupercalia.
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The earliest known association of the Feast of St. Valentine to romance was in a poem by Geoffrey Chaucer titled Parliament of Fowls from 1382, where he mentioned St. Valentine's Day as the day when birds would start mating.
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Valentine's Day became associated with love and romance in the 15th century, with the tradition of giving Valentine's cards starting as love letters, and it even received a mention in Shakespeare's Hamlet.
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In the 19th century, the popularity of creating Valentine's Day cards exploded in England, with over 400 cards being sent in 1840, and pre-made cards eventually replacing handwritten letters. American Esther Howland sold the first mass-produced Valentine's cards in the United States, leading to the modern greeting card industry.
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Over 20 billion dollars is spent on Valentine's Day in the United States, with 75% of the money being spent by men.
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Valentine's Day is not an official holiday in any country and the Catholic Church removed it from the calendar in 1969, but you can visit the Basilica di Santa Maria in Rome to see the exhumed skull of the original Saint Valentine.