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There are more tales of the "origins" of Valentine's Day than arrows in Cupid's quiver. As expected, most have something to do with pagan ritual (pretty much every holiday—from Christmas to Mother's Day—has something to do with pagan ritual). Four centuries before Christ, Romans had a day called Lupercalia. Without going too much into it, I'll sum it up as a sexual lottery. Pull names out of a box at random and couple with a young member of the opposite sex. After a year, you get to pick another name.Supposedly, this went on for centuries until the Christians had to go and ruin it with their whole morality thing.
But apparently Christians didn't think the practice was all bad. They (Pope Gelasius, according to my source) liked the box idea, and so initiated a custom of drawing saints names out of a box. Whoever's name you drew, you were supposed to emulate for the year. Pity the poor person drawing Simeon Stylites, who spent his life on the top of a pillar, never leaving it for any reason.
But who is this Valentine guy, anyway? Probably he was a martyr buried on February 14 with little or no connection to the dispersal of romantic love. Nevertheless, there are legends.
One story is that Valentine was a priest who secretly performed marriages when Emperor Claudius II reportedly forbade marriage (in an effort to ensure he had soldiers without family ties). Another story says that he was a Christian imprisoned for his faith, and cured his jailer's daughter of blindness. The day before his execution (supposedly Feb. 14, 269), he sent a farewell message to the daughter signed "From your Valentine."
True or not (skeptics are forgiven), Valentine's Day has been a big deal at least since the Middle Ages. In his Pariliament of Foules, Geoffrey Chaucer adds another legend: "For this was sent on Seynt Valentyne's day / When every foul cometh ther to choose his mate." About that same time, the first modern valentines were produced. The first card was sent by Charles, duke of Orleans, to his wife in 1415 when he was a prisoner in the Tower of London. It's still on display at the British Museum. ...