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Valentine’s Day appears to have originated in the Middle Ages to honor Saint Valentine. However, several “Valentines” have been proven to exist, so which one is being honored is sort of a guess. One unfortunate
Valentine was imprisoned (for who knows what crime) and fell in love with the jailer’s daughter. He sent her romantic letters, which were exquisitely hand decorated and signed “From Your Valentine.” Even today, perhaps
modeled on such a fellow, St. Valentine is the patron saint of dating or engaged couples.

However, the actual custom of secretly sending valentines or of putting them in something belonging to a person (hopefully, to be found) comes to us from the Romans. While celebrating the feast of Lupercalia, honoring the pastoral god Lupercus (who repelled wolves), maidens’ names were drawn from a box and paired with the names of young men. These couples had to stay “paired” for a year and participate in ceremonies, games, etc., together. The French later embellished the early Roman practice by having both men and women draw the opposite sex names from boxes. In England, between 1660 to 1685, women drew men’s names in a type of lottery and then the man had to give the respective woman a present. During the later years of the Roman empire, Valentine was a priest (supposedly) who married soldiers in the Roman army despite (and in spite of) orders that stated soldiers could not marry while actively serving. (Some legends say he was put to death for that activity.)

Earlier, in the Middle Ages, young English women followed the superstitious practice of trying to cast spells to locate true loves, while young Italian women rose before dawn and peeked out of their bedroom windows hoping to espy their true loves. German maidens planted onions and placed slips of paper, with men’s names written on them, near the holes. Whichever onion grew first indicated which man a girl would/should marry. Valentine messages’ popularity also grew and fully flowered when, in 1723, valentine writers made booklets which contained a variety of sayings, short poems, and messages which people could copy (designed for the hopelessly unromantic and unimaginative). By 1800, valentine “cards” appeared for sale-pre-decorated. For a person with a mean streak, in the early to mid-1800s there were “Penny Dreadful” and “Rude and Crude” valentines to send to people one disliked. They were “all the rage,” but some post offices in the United States refused to deliver them because they
were emotionally cruel and/or obscene. On a sweeter note, sugar candy valentines with little sayings (made by Necco) first were sold in 1902. At present, it is estimated that Valentine’s Day cards are second in number sent yearly only to Christmas cards.

Sources: various encyclopedias and folklore books, PTA newsletters, newspaper articles, etc.