Who would have thought men running through Roman cities slapping women with goat hides would lead to a modern romantic holiday filled with lacy hearts and chubby, arrow toting, winged boys? But St. Valentine's Day is indeed thought to have its roots in the ancient Roman holiday Lupercalia. The celebration, thought to ward off evil and secure fertility, included the hide slapping fun along with the tradition of putting all eligible women's names in an urn so men could pick one out to romantically couple up for the following year. Historically, Lupercalia was celebrated on February 15th, but in an attempt to re-invent a Pagan holiday as a Christian one, Pope Gelasius I declared February 14th to be St. Valentine's Day in A.D. 496. Which St. Valentine the Pope meant to honor with the holiday remains unclear although there are three widely recognized candidates, one a priest in Rome, one a bishop in Terni, and one that almost nothing is know about other than that he died in Africa.

The most popular legends surround the St. Valentine from Rome. His story has different variants but the most common themes include St. Valentine defying the Roman Emperor Claudius II by refusing to give up Christianity and by continuing to marry young men who were going off to fight as soldiers after Claudius declared no soldiers were to marry, thinking single men make better warriors. St. Valentine was put in jail and sentenced to death. While in jail he is said to have sent a letter to the jailor's daughter on the eve of his execution, signing it "With love, from your Valentine". The jailor's daughter was thought to either have been the betrothed of St. Valentine, the subject of a miracle the Saint performed while in jail to cure her blindness, or both.

St. Valentine was executed on February 14th, hence the date chosen for the holiday. Others link February 14th to the date when birds choose a mate. This idea most likely comes from Chaucer's "The Parliament of Fowls", a poem written for England's Richard II and fiance, where he links St. Valentine's Day with romance and the pairing up of birds.

While St. Valentine is still the namesake of this romantic holiday, common symbols associated with the day also include Cupid (in Roman mythology the son of Venus, in Greek mythology the son of Aphrodite), heart shapes, and the color red. St. Valentine's Day is the second largest card sending holiday (Christmas being number one) according to the Greeting Card Association. Common celebratory practices include exchanging "valentines" with friends and loved ones and giving candy and flowers to ones sweetheart. Most countries have a "day of love" they recognize but not all coincide with the February 14th holiday. St. Valentine's Day as it is known on February 14th is practiced by most western countries and has gained recent popularity in places such as United Arab Emirates, India, Japan, and China. It is a particularly popular holiday in South Africa where it is celebrated with great fervor. It is not an official government holiday anywhere.