Some believe Valentine actually sent the first 'valentine' greeting himself wile in prison.  They say he fell in love with a young girl -- possibly the jailer's daughter -- who visited him during his confinement. Before his death, it is alleged that he wrote her a letter, which he signed “From your Valentine.”

Other stories suggest that Valentine may have been killed for attempting to help Christians escape harsh Roman prisons where they were often beaten and tortured.

Many dispute these tales, however. Today, the Catholic Church recognizes at least three different saints named Valentine (or Valentinus), all of whom were martyred.  It is unclear which, if any, of these three Valentines is the namesake for the romantic holiday.

What we do know is that February had been regarded as a month of romance long before the legends of Valentine surfaced.  In ancient Rome, February 14th was set aside to honor Juno, the goddess of marriage.  The next day was Lupercalia, a fertility festival dedicated to Faunus, the god of agriculture, and to the Roman founders Romulus and Remus.  

To begin the festival, members of the Luperci, an order of Roman priests, would gather at the cave where the infants Romulus and Remus, the founders of Rome, were believed to have been cared for by a she-wolf or lupa. The priests would then sacrifice a goat, for fertility, and a dog, for purification.  The goat's hide would be cut into strips and dipped in the sacrificial blood.  The priests would then take to the streets and gently slap both young women and the crops with the strips. Roman women welcomed being touched with the hides because it was believed the strips would make them more fertile in the coming year. 

Later in the day, all the young women would place their names in a large jar. Then the bachelors would each draw a name out of the jar and were paired for the year with the woman whose name they drew. These matches often ended in marriage.