At least three recognized saints bear the name Valentine and the true explanation of which one is celebrated on Valentine’s Day is a mystery lost to the ages. Scholars do know that the holiday began as a liturgical celebration, or feast day, in the Roman Catholic Church. It’s likely - though we may never know for certain - that the day was intended to honor Valentine of Rome, a priest who was executed for his actions against the Roman Empire and buried on February 14.
Saint Valentine, or Valentinus as his associates would have known him, was a priest who lived during the period of the Roman Empire. Emperor Claudius II believed that single men were better soldiers than married men and he made it a crime for young men to marry. Valentine was imprisoned and sentenced to death for performing the marriage ceremonies of young soldiers and for ministering to Christians. It seems Saint Valentine had another divine skill - healing. During his imprisonment, Saint Valentine is said to have healed the daughter of his jailor. He may have been smitten with her as well; before was put to death, Valentine wrote her a farewell letter and signed it, "Your Valentine".
About 200 years after the death of Valentine of Rome, Pope Gelasius named February 14 St. Valentine Day. Some scholars believe that the date was chosen not because of Valentine’s alleged burial date, but as an alternative to a mid-February pagan holiday known as Lupercalia, a fertility festival in which young, unmarried women would place their names in an urn and the town’s bachelors would chose a name of a girl to be paired with for the rest of the year – an early form of dating. Sometimes marriages would result.
Despite the fact that Saint Valentine was executed for uniting forbidden lovers (kicking off the whole notion of someone being your "valentine") and that the pagan holiday rumored to be the inspiration for the date’s selection also paired off couples, the romantic connotation of Valentine's Day didn't emerge until the Middle Ages. By the 18th century in England, February 14 had become a day when people expressed their love for one another by exchanging presents, handmade cards (known as valentines) and, of course, sweets.
Here are some other legends associated with the day: