The history of Valentine's Day — and its patron saint — are shrouded in mystery. But we do know that February has long been a month of romance. St. Valentine's Day, as we know it today, contains vestiges of both Christian and ancient Roman tradition. Every February, across the country, candy, flowers, and gifts are exchanged between loved ones, all in the name of St. Valentine. Some experts state that it originated from St. Valentine, a Roman who was martyred and died on February 14, 269 A.D., the same day that had been devoted to love lotteries. In the Middle Ages, people began to send love letters on Valentine's Day. Medieval Europeans believed that birds began to mate on February 14.

Valentine's Day started in the time of the Roman Empire. In ancient Rome, February 14th was a holiday to honor Juno. Juno was the Queen of the Roman Gods and Goddesses. The Romans also knew her as the Goddess of women and marriage. The following day, February 15th, began the Feast of Lupercalia. During festival time, women would write love letters, also known as billets, and leave them in a large urn. The men of Rome would then draw a note from the urn and they would then be partners for the duration of the festival with the girl whom he chose. Sometimes the pairing of the two lasted an entire year, and often, they would fall in love and would later marry. Some 800 years later in 496 A.D., Pope Gelasius wanted the church to distance itself from such pagan rituals and he changed the lottery to have both young men and women draw the names of saints whom they would then emulate for the year (a change that no doubt disappointed a few young men). Instead of Lupercus, the patron of the feast became Valentine. For Roman men, the day continued to be an occasion to seek the affections of women, and it became a tradition to give out handwritten messages of admiration that included Valentine's name.

Under the rule of Emperor Claudius II, Rome was involved in many bloody and unpopular campaigns. Claudius the Cruel was having a difficult time getting soldiers to join his military leagues. He believed that the reason was that Roman men did not want to leave their loves or families. As a result, Claudius canceled all marriages and engagements in Rome. The good Saint Valentine was a priest at Rome in the days of Claudius II. He and Saint Marius aided the Christian martyrs and secretly married couples, and for this kind deed Saint Valentine was apprehended and dragged before the Prefect of Rome, who condemned him to be beaten to death with clubs and to have his head cut off. He suffered martyrdom on the 14th day of February, about the year 270. Legend also says that St. Valentine left a farewell note for the jailer's daughter, who had become his friend, and signed it "From Your Valentine".

It was Chaucer who first linked St. Valentine's Day with romance, according to UCLA medieval scholar Henry Ansgar Kelly, author of Chaucer and the Cult of Saint Valentine,. In 1381, Chaucer composed a poem in honor of the engagement between England's Richard II and Anne of Bohemia. As was the poetic tradition, Chaucer associated the occasion with a feast day. In "The Parliament of Fowls," the royal engagement, the mating season of birds, and St. Valentine's Day are linked: "For this was on St. Valentine's Day, When every fowl cometh there to choose his mate."

Many historians believe the custom of sending poetic verse on this day originated with the capture of Charles, Duke of Orleans, during the Battle of Agincourt. From his prison cell in the Tower of London, Charles sent his wife a rhyming love letter. Gradually, February 14 became the date for exchanging love messages and St. Valentine became the patron saint of lovers. The date was marked by sending poems and simple gifts such as flowers. There was often a social gathering or a ball. Valentine cards became popular in Great Britain in the nineteenth century. Noted artist Kate Greenaway created cards which featured joyful children and beautiful gardens. Other card manufacturers emphasized Cupid, the pudgy, winged son of Venus, the goddess of love. In Roman lore, Cupid is known as Eros, the son of Aphrodite.

Esther A. Howland (1828-1904) of Worcester, Massachusetts, became one of the first U.S. manufacturers of valentines. As an impressionable young student at The Mount Holyoke Female Seminary, Class of 1847, and a contemporary of the young poet Emily Dickinson, Esther had been exposed to the annual Valentine festivities, which were later banned by the college for being too frivolous! After graduating at the age of nineteen, she received an elaborate English Valentine from one of her fathers' business associates, and was confident that she was capable of making similar — even better ones. She convinced her father to order lace paper and other supplies from England and New York City and, with characteristic determination, made a dozen samples, which her brother added to his inventory for his next sales trip. Secretly hoping for as much as $200 In orders, they were stunned when her brother returned with more than $5000 in advance sales — more than she could hope to make herself. Recruiting friends and creating her now-famous assembly line, her business was born. Advertising and word-of-mouth, based on a beautiful product and a wide range of prices, led to a $100,000. per year business, and assured this ingenious woman a place in history. Her valentines were known from Maine to California, and today's collectors can often recognize them by their characteristic refinement and detail.

Many valentines of the 1800's were hand painted. Some featured a fat cupid or showed arrows piercing a heart. Many cards had satin, ribbon, or lace trim. Others were decorated with dried flowers, feathers, imitation jewels, mother-of-pearl, sea shells, or tassels. Some cards cost as much as $10. Verses and Valentine greetings were popular as far back as the Middle Ages, when lovers said or sang their valentines. The oldest "valentine" in existence was made in the 1400's and is in the British Museum. Paper valentines were exchanged in Europe where they were given in place of valentine gifts. Paper valentines were especially popular in England. Early valentines were made by hand and were made with colored paper, watercolors, and colored inks. There were many different types of handmade valentines, including:

Acrostic Valentines - had verses in which the first lines spelled out the loved one's name

Cutout Valentines - made by folding the paper several times and then cutting out a lace-like design with small, sharp, pointed scissors

Pinprick Valentines - made by pricking tiny holes in a paper with a pin or needle, creating the look of lace.

Theorem or Poonah Valentines - designs that were painted through a stencil cut in oil paper, a style that came from the Orient.

Rebus Valentines - verses in which tiny pictures take the place of some of the words (an eye would take the place of the word "I").

Puzzle Purse Valentines - a folded puzzle to read and refold. Among their many folds were verses that had to be read in a certain order.

Fraktur Valentines - had ornamental lettering in the style of illuminated manuscripts of the Middle Ages.

Penny Dreadfuls - From the mid-1800's to the early 1900's, many people sent comic valentines called penny dreadfuls. These cards sold for a penny and featured such insulting verses as: 'Tis all in vain your simpering looks, You never can incline, With all your bustles, stays, and curls, To find a valentine.