Valentine’s Day has a long history that dates back to the birth of the Roman Empire. According to legend, two twins named Regulus and Romulus were cast out as newborns. A servant was supposed to place them in the Tiber River to drown, but instead placed them in a basket which swept them away safely. They were initially cared for by a she-wolf before being taken in by a shepherd and his wife. The twins went on to found Rome and the festival of Lupercalia emerged in the name of a god worshipped by the shepherds: Lupercus. The festival took place in mid-February and festivities commenced in the den of the she-wolf, Lupercal cave, with a sacrifice. There are multiple slightly altered accounts of the festival, but at its simplest: the sacrifice is followed by a feast that would conclude with at least two Roman priests, running around in some state of indecency while slapping women with strips of goat hide, thought to promote fertility. The festival also included pairing off couples by lottery who were to remain together for at least the duration of the festivities.
Lupercalia eventually met its demise in the fifth century CE. The Roman Catholic church replaced the festival with the Feast of Saint Valentine, a holiday to commemorate the martyrdom of a certain Saint Valentine.

Christianity was criminalized in the early eras of the Roman Empire. Its theology did not worship the pagan gods nor recognize the deified emperors of the empire’s past, such as Augustus Caesar, along with its mythological founders Regulus and Romulus. Christianity also valued holy matrimony, a sacred covenant that overpowered a soldier’s obligation to the state, the root of the legend of Saint Valentine.
Legend has it that Saint Valentine was a priest who married couples in secret during a time when the empire had outlawed marriage. Valentine was caught, and executed for his crimes on February 14. Another legend says that while he was imprisoned, Valentine befriended the daughter of his prison guard and wrote her a letter before his execution, which he signed “from your Valentine.” In some tellings the daughter was blind and Valentine was attributed to miraculously curing her sight.
It was not until the poets got a hold of the holiday that it became associated with love, as opposed to Saint Valentine himself. The earliest evidence of this connection dates to the 14th-century poet Geoffrey Chaucer and his poem “Parlement of Foules.” At this time, February 14 was acknowledged as the beginning of spring which brought forth the birds and commenced mating season. Chaucer sets his poem at this moment and refers to the date as Saint Valentine’s Day.
Written valentines began to emerge in the 15th century. Charles d’Orléans, the grandson of King Charles V of France is commonly accredited with the earliest surviving written valentine: a letter he wrote to his wife while imprisoned in England. The letter read: “Je suis desja d’amour tanné, ma tresdoulce Valentinee:” translated to English, “I am already weary of love, my very sweet Valentine.” However, the letter is not a letter, but a fictional poem he wrote after he was released, regarding the old Lupercalian practice of matchmaking lotteries.
The trend of valentines increased in literature and by the 18th century, the exchange of handwritten valentines cards emerged. It was not until the industrial age and inventions such as the printing press emerged that commercialization struck which led to the holiday that we know today.