This weekend, couples across the country will celebrate the day of romance, also known as Valentine’s Day. A 1600-year-old holiday, here are five surprising facts about the history and origins of St. Valentine’s Day.

The Original St. Valentine is Still a Mystery

Although Pope Gelasius I initially established Valentine’s Day in the 5th century, there are actually three different so-called “Valentines or Valentinus’” who inspired the holiday. One Valentine lived during the reign of Emperor Claudius II, who decreed that no young man could marry in order to bolster his troops.

St. Valentine defied the order and continued to marry young couples in secret. He was put to death for his acts of love.

The other strong possibility is Saint Valentine of Terni. It must have been something in the water of the ancient Romans as this Valentine also lived and was put to death outside Rome during the reign of Emperor Claudius II.

In Terni’s Basilica di San Valentino, Saint Valentine of Terni’s remains are enshrined in glass on top of the main altar of the cathedral (though apparently his skull resides in a glass reliquary in Rome’s Basilica di Santa Maria). Visitors can also descend below the altar to see his original resting place. People have been known to leave notes behind of “gratitude and love to the saint.”

Valentine’s Day Was Initially a Pagan Holiday

There may be three so-called “Saint Valentines” in the history of the Catholic church, but there was only one pagan celebration of Lupercalia, which took place in order to honor the she-wolf who took in Rome’s legendary founders Romulus and Remus and to please Lupercus, a Roman fertility god. Initially celebrated on February 15, the day is described as a “bloody, violent and sexually-charged celebration awash with animal sacrifice, random matchmaking and coupling in the hopes of warding off evil spirits and infertility.”

As with so many other pagan holidays, the early Christian church tried to work within that existing structure and create new, religious holidays focused on faith. Eventually, the pagan event was labeled “un-Christian” and outlawed, being replaced with Valentine’s Day, which grew in popularity over the centuries.

The First Valentine is 600 Years Old

Want to impress your loved one this holiday? Try using a line from the oldest preserved Valentine, written in 1415 by Charles, Duke of Orleans from his prison cell in the Tower of London after the Battle of Agincourt between the French and the English

From his prison cell, he wrote in part, “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.”

Sadly, like the somberness of the note, this relationship didn’t have a happy ending. Charles remained in prison for 25 years and was released after his “very gentle Valentine” had died. His Valentine is now preserved in the British Library in London.

“Mother of the Valentine”

Even in the early 1700s, Valentine’s Day was already a popular holiday in the United States. By the 1840s, Esther Howland was the first to mass produce Valentine’s Day cards. She made them often with “real lace, ribbons and colorful pictures known as ‘scrap.’”

An entrepreneur, she sold her father, who owned a stationery factory, on the idea of producing Valentine’s Day cards similar to one she had from Britain. She went out expecting maybe a couple of hundred orders, but instead, she received 5,000. In order to fill every request, she hired an army of women to help.

Howland herself never married but did eventually sell her business 40 years later to her greatest competitor, George C. Whitney. If any of her original Valentine’s Day cards hit the market, they can sell anywhere from around $300 to $400.

St. Valentine’s Day Massacre

One of the most famous events associated with Valentine’s Day is the St. Valentine’s Day Massacre, which most believe was orchestrated by the legendary gangster Al Capone.

In the 1920s and 1930s, Chicago was well-known as a popular hangout and destination for a variety of gangsters. From Capone to John Dillinger, the Windy City was no stranger to violence. However, the St. Valentine’s Day Massacre shocked the world, when seven Irish gangsters associated with George “Bugs” Moran were gunned down by several men dressed as police officers.

It remains one of the biggest unsolved crimes in the history of the country.

From a 600-year-old Valentine to the St. Valentine’s Day Massacre, the world’s most romantic holiday has a long and sordid history. But as couples gather this frigid Valentine’s Day, hopefully they can find a little romance and less animal sacrifice or gangster related shootouts.

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