Emperor Claudius II outlawed marriage for young men when they were thinking they should spend their youth as soldiers. Valentine performed secret marriages for many young couples until he was caught and executed.
Another legend is that St. Valentine sent the first Valentine’s Day card.
While in jail waiting to be executed, he slipped a note to his sweetheart, signing it: “From your Valentine.”
Legend also has it that he cured the jailer’s blindness before being executed. The jailer and his family converted to Christianity.
Source: littlethings.com
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