TRADITIONALLY, mid-February was a Roman time to meet and court prospective mates. Valentine’s Day probably derived from the ancient Roman feast of Lupercalis (February 15), also called the Lupercalia. In an annual rite of fertility, eligible young men and women would be paired as couples through a town lottery. Scantily clad or naked men would then run through the town carrying the skins of newly sacrificed goats dipped in blood. The women of the town would present themselves to be gently slapped by the skins, and marked by the blood, to improve their chances of conceiving in the coming year.
After Christianity came to dominance in Europe, pagan holidays such as Lupercalia were frequently renamed for early Christian martyrs. In 496 AD, Pope Gelasius officially declared February 14 to be the feast day of two Roman martyrs, both named Saint Valentine, who lived in the third century. Neither of the Saints Valentine seems to have had an obvious connection to courtship or lovers.

The Lupercalian lottery
Under penalty of mortal sin, Roman young men instituted the custom of offering women they admired and wished to court handwritten greetings of affection on February 14. The cards acquired St. Valentine’s name.
As Christianity spread, so did the Valentine’s Day card. The earliest extant card was sent in 1415 by Charles, Duke of Orleans, to his wife while he was a prisoner in the Tower of London. It is now in the British Museum.
In the sixteenth century, St. Francis de Sales, Bishop of Geneva, attempted to expunge the custom of cards and reinstate the lottery of saints’ names. He felt that Christians had become wayward and needed models to emulate. However, this lottery was less successful and shorter-lived than Pope Gelasius’s. And rather than disappearing, cards proliferated and became more decorative.

Proliferation of cards
By the seventeenth century, handmade cards were oversized and elaborate, while store-bought ones were smaller and costly. In 1797, a British publisher issued ‘The Young Man’s Valentine Writer’, which contained scores of suggested sentimental verses for the young lover unable to compose his own. By the 18th century, it was common for friends and lovers to exchange handwritten notes on Valentine’s Day.
Printed cards had largely replaced written sentiments by the 19th century. In 1840, Esther Howland of Worcester, Massachusetts, created the first line of mass-produced Valentine’s Day cards for sale.
Cupid, the naked cherub armed with arrows dipped in love potion, became a popular Valentine’s Day image. He was associated with the holiday because, in Roman mythology, he is the son of Venus, goddess of love and beauty.
Printers had already begun producing a limited number of cards with verses and sketches, called “mechanical valentines”, and a reduction in postal rates in the next century ushered in the less personal but easier practice of mailing Valentines. Today, Valentine’s Day is second only to Christmas as the most popular card-sending holiday.