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Modern day St. Valentine's celebrations are said to have been derived from both ancient Christian and Roman tradition. However, it is said that the holiday originated from the ancient Roman festival of Lupercalis/Lupercalia, a fertility celebration that used to observed annually on February 15.

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The rise of Christianity in Europe saw many pagan holidays being renamedfor and dedicated to the early Christian martyrs. Lupercalia was no exception. In 496 AD, Pope Gelasius turned Lupercalia into a Christian feast day and set its observance a day earlier, on February 14. He proclaimed February 14 to be the feast day in honour of Saint Valentine, a Roman martyr who lived in the 3rd century.

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Lupercalia was held in the spring and regarded as a festival of purification and fertility. Each year on February 15, the Luperci priests gathered on Palantine Hill at the cave of Lupercal (supposedly where the she-wolf had suckled and raised Romulus and Remus the twin royal heirs and founders Rome). Vestal virgins brought sacred cakes made from the first ears of last year's grain harvest to the fig tree. Two naked young men, assisted by the Vestals, sacrificed a dog and a goat at the site. The blood was smeared on the foreheads of the young men and then wiped away with wool dipped in milk.

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The youths then donned loincloths made from the skin of the goat and led groups of priests around the pomarium, the sacred boundary of the ancient city, and around the base of the hills of Rome. The occasion was happy and festive. As they ran about the city, the young men lightly struck women along the way with strips of the goat hide. It is from these implements of purification, or februa, that the month of February gets its name. This act supposedly provided purification from curses, bad luck, and infertility.

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Long after Palentine HIll became the seat of the powerful city, state and empire of Rome, the Lupercalia festival lived on. Roman armies took the Lupercalia customs with them as they invaded France and Britain. One of these was a lottery where the names of available maidens were placed in a box and drawn out by the young men. Each man accepted the girl whose name he drew as his love - for the duration of the festival, or sometimes longer.

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The reason behind the current name of this day is a kindly cleric named Valentine who died more than a thousand years ago. Apart from his name, nothing is known for certain of Saint Valentine except that he was supposedly executed on February 14, 270 AD buried on the Via Flaminia the same day. Legend has it that Valentine was a priest who refused an unattested law attributed to Roman Emperor Claudius II, allegedly ordering that young men remain single. The Emperor supposedly did this to grow his army, believing that married men did not make for good soldiers. The priest Valentine, however, secretly performed marriage ceremonies for young men. When Claudius found out about this, he had Valentine arrested and thrown in jail. In an embellishment to the legend, on the evening before Valentine was to be executed, he wrote the first "valentine" himself, addressed to a young girl variously identified as his beloved, as the jailer's daughter whom he had befriended or healed of blindness, or both. It was a note that read "From your Valentine."

Arguably, one could say the very first valentine cards were the slips of paper bearing names of maidens the early Romans first drew. Or perhaps that note Valentine passed from his death cell.​