Certain holidays are so simple on the surface that we never dive too deeply into how or why they came to be, and we housesellers think Valentine's Day qualifies as one of those holidays. But the history of the day celebrating love, lovers and friendship is far more strange and unusual than what the holiday has become. The main thing most scholars agree on is that the holiday has its origins in the ancient Roman festival of Lupercalia, held in mid-February, which celebrated the coming of Spring and included fertility rites and the pairing off of women with men by lottery. Oh, and the men sacrificed a goat and a dog and then whipped women with the hides of the animals they had just slain. So... not quite as romantic as roses and dinner at a fancy restaurant. 

At the end of the 5th century, Pope Gelasius I replaced Lupercalia with what would become St. Valentine’s Day. The Pope expelled many of the Pagan rituals such as the rampant nudity and drunkenness, and the holiday was then named after not one, but two men named Valentine (there are actually at least three St. Valentines throughout history). Both were executed by the Roman Emperor Claudius II on February 14, one in 269 A.D. and the other in 270 A.D. It is believed that Claudius didn’t want Roman men to marry during wartime (married men were thought to make lesser soldiers) but one of the Valentines went against his wishes and performed secret weddings, leading to his arrest and execution.

The other Valentine, and the one most associated with the spirit of the modern day version of the holiday, was thought to have been killed for attempting to help Christians escape harsh Roman prisons, where they were often beaten and tortured. As legend has it, an imprisoned Valentine actually sent the first “valentine” greeting himself after he fell in love with a young girl–commonly thought to be his jailor’s daughter–who visited him during his confinement. It is alleged that he wrote her a letter shortly before his execution and signed it “...from your Valentine,” thus inspiring the expression that is still in use today. By the time of the Middle Ages, and with help from writers such as Chaucer and Shakespeare, the stories all emphasize his appeal as a sympathetic and heroic romantic figure.