Tradition holds that the first Valentine was sent in 270 A.D. by St. Valentine himself on the eve of his execution for refusing to renounce Christianity. Signed "from your Valentine", it was a note of appreciation from the young cleric to his jailer’s blind daughter who had brought him food and delivered messages for him.

The Romans celebrated St. Valentine’s Day as the Feast of Lupercalia, dedicated to the pastoral god Lupercus and to the Goddess of Love, Juno. The birds of Italy began mating on February 14, the oracles observed. Roman maidens placed their names in an urn set up in the public square and courageous bachelors drew from it to obtain their "blind date" for the coming year. The Christian Church denounced these "love lotteries" as pagan rituals. During the Middle Ages, "love lotteries" persisted in France as "chance boxes" that allotted couples one year to get married or part company and, in England, men wore the name of the girl they drew on their sleeve encircled with a heart.

Written Valentines appeared around the year 1400 as quaint love missives and many were anonymous. Church opposition gradually declined and, by the 1700s, the familiar "roses are red, violets are blue…" verses were popular and in France, Valentines grew in size and elegance featuring ribbons, lace, gilt and other intricate effects made by hand.

The first Valentines in America were exchanged during the Revolutionary days and were mostly handmade with sentimental verses written in a flowing script. In 1840, Miss Esther Howland, an imaginative artist and entrepreneur became the first regular publisher of Valentines in the United States. She became a successful businesswoman heading her own publishing firm specializing in Valentine cards.

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