Valentine's Day is actually St. Valentine's Day, created to honor the Saint Valentine. He was a priest in third century Rome. Claudius II, the Emperor, decided that marriages should be outlawed. Valentine decide to marry couples anyway and was later killed for it. (The ban was only on young men because Claudius wanted them to be soldiers.)
The reason that it is celebrated in the middle of February is up for debate. Some believe that is the day Saint Valentine was martyred. Others believe it was placed there to interfere with the Pagan festivals that were during the middle of February.
498 AD was when St. Valentine's Day was officially declared a holiday by the Pope.
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