Valentine's Day was named after its patron saint, St. Valentine, but there's actually at least two men named Valentine that could've inspired the holiday, including one Valentine who was a priest in third century Rome. As the story goes, this Valentine defied Emperor Claudius II's ban on marriage (he thought it distracted young soldiers), illegally marrying couples in the spirit of love until he was caught and sentenced to death. Another legend suggests that Valentine was killed for attempting to help Christians escape prison in Rome, and that he actually sent the first "valentine" message himself while imprisoned, writing a letter signed "From your Valentine."
The medieval English poet Geoffrey Chaucer, author of The Canterbury Tales, often took liberties with history, placing his poetic characters into fictitious historical contexts that he represented as real. No record exists of romantic celebrations on Valentine’s Day prior to a poem Chaucer wrote around 1375. In his work “Parliament of Foules,” he links a tradition of courtly love with the celebration of St. Valentine’s feast day–an association that didn’t exist until after his poem received widespread attention. The poem refers to February 14 as the day birds (and humans) come together to find a mate. When Chaucer wrote, “For this was sent on Seynt Valentyne’s day / Whan every foul cometh ther to choose his mate,” he may have invented the holiday we know today.
Cupid is often portrayed on Valentine’s Day cards as a naked cherub launching arrows of love at unsuspecting lovers. But the Roman God Cupid has his roots in Greek mythology as the Greek god of love, Eros. Accounts of his birth vary; some say he is the son of Nyx and Erebus; others, of Aphrodite and Ares; still others suggest he is the son of Iris and Zephyrus or even Aphrodite and Zeus (who would have been both his father and grandfather). According to the Greek Archaic poets, Eros was a handsome immortal played with the emotions of Gods and men, using golden arrows to incite love and leaden ones to sow aversion.
Americans probably began exchanging hand-made valentines in the early 1700s. In the 1840s, Esther A. Howland began selling the first mass-produced valentines in America. Howland, known as the “Mother of the Valentine,” made elaborate creations with real lace, ribbons and colorful pictures known as “scrap.” Today, according to the Greeting Card Association, an estimated 145 million Valentine’s Day cards are sent each year, making Valentine’s Day the second largest card-sending holiday of the year (more cards are sent at Christmas).
While valentines are traditionally known for being affectionate and sweet, another option was also common. For those not on good terms, or who wanted to fend off an enemy or unwanted suitor, “vinegar valentines” offered a stinging alternative.
Weirdly enough, the story of conversation hearts first began when a Boston pharmacist named Oliver Chase invented a machine that simplified the way medical lozenges — used for sore throats and other illnesses — could be made. The result was America's first candy-making machine, because the pharmacist soon started shifting his focus from making lozenges to candy instead! Chase founded the New England Confectionery Company, or Necco, and the candy lozenges soon became what we know today as Necco wafers. It was Oliver's brother, Daniel Chase, who started printing sentimental messages on the Necco sweethearts.
The first heart-shaped box of chocolates was introduced in 1861. It was created by Richard Cadbury, son of Cadbury founder John Cadbury, who started packaging chocolates in fancy boxes to increase sales. Today, more than 36 million heart-shaped boxes of chocolates are sold each year. That's 58 million pounds of chocolate!
Giving red roses may be an obvious romantic gesture today, but it wasn't until the late 17th century that giving flowers became a popular custom. The practice can be traced back to when King Charles II of Sweden learned the "language of flowers", which pairs different flowers with specific meanings, on a trip to Persia, and subsequently introduced the tradition to Europe. The act of giving flowers then became a popular trend during the Victorian Era, including on Valentine's Day, with red roses symbolizing deep love.