Historians have traced the origin of Valentine's Day to the ancient Roman Empire. It is said that in the Rome of ancient times people observed a holiday on February 14th to honor Juno - the Queen of Roman Gods and Goddesses. The Romans also regarded Juno as the Goddess of Women and Marriage. On the following day, February 15th began the fertility festival called 'Feast of Lupercalia'. The festival of Lupercalia was celebrated to honor the Gods Lupercus and Faunus - the Roman God of Agriculture besides the legendary founders of Rome, Romulus and Remus.
An interesting custom was followed in the Feast of Lupercalia to bring together young boys and girls who otherwise were strictly separated. On the eve of the festival names of young Roman girls were written on a slip of paper and placed into jars. Each young man drew out a girl's name from the jar and was paired with the girl for the duration of Lupercalia. Sometimes pairing lasted for a year until next year's celebration.
Quite often, the couple would fall in love with each other and later marry. The custom lasted for a long time until people felt that the custom was un-Christian and that mates should be chosen by sight, not luck.
Reference: www.stvalentinesday.org/