How did Valentine’s Day start? Having a particular Valentine’s Day is a very old tradition, thought to have originated from a Roman festival. The Romans had a festival called Lupercalia in the middle of February — officially the start of their springtime. PenguinsGetty Images It’s thought that as part of the celebrations, boys drew names of girls from a box. They’d be boyfriend and girlfriend during the festival and sometimes they’d get married. Later on, the church wanted to turn this festival into a Christian celebration and decided to use it to remember St Valentine too. Gradually, St Valentine’s name started to be used by people to express their feelings to those they loved.