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The legend of St. Valentine is not absolutely clear, which is also why we refer to this history as "legend." One legend portrays him as a priest who refused the Roman Emperor Claudius II's law, ordering that young men remained single. It is argued that Claudius II 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 Catholic men. When Claudius found out about this, he had Fr. Valentine arrested and thrown in jail. Claudius had meetings with Fr. Valentine and grew fond of him and even attempted to get Fr. Valentine to convert to the Roman paganism which he practiced. Instead, Fr. Valentine refused and attempted to convert Claudius to the Catholic faith. This enraged Claudius, and he sentenced Valentine to death. While imprisoned, one of the jailors had a blind daughter, whom he brought to the jail often, and she spoke at length to Fr. Valentine. Just before he was put to death, he sent her a small card and signed it, "From your Valentine."
Another story has it that while Fr. Valentine was imprisoned, people would leave him little notes, folded up and hidden in cracks in the rocks around his cell. He would find them and offer prayers for them.
Either way, the origin of the modern "Valentine Card" came from notes either to or from Fr. Valentine while he was in prison.
Fr. Valentine was put to death on February 14, 270 AD (some sources say 269, others 273 AD).