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The link between romance and the middle of February goes back to the English poet Geoffrey Chaucer. In a 1381 poem celebrating a royal engagement, he linked the mating of birds with the festival of the Roman martyr, St. Valentine.
By the 18th century, the English had established the custom of choosing a friend or sweetheart to receive a valentine, and the practice crossed to North America. Early valentines, which were handmade, were often friendly or playful, but as time went on, they tended to become more serious and sentimental. Poems or extracts, written by the sender or copied from a book, were lushly romantic. There were exceptions: Catharine Parr Traill spent a day in 1838 writing out valentines for her nephews and nieces.
The advent of the printed card in the 1850s commercialized the custom and made it more like the modern practice of sending and receiving many valentines. The cards themselves were often highly decorative (Ward, 92, 96-98).
More Love Messages
Noël, Françoise. Family Life and Sociability in Upper and Lower Canada, 1780-1870: A View from Diaries and Family Correspondence. Montréal: McGill-Queen's University Press, 2003.
Ward, W. Peter. Courtship, Love and Marriage in Nineteenth-Century English Canada. Montréal: McGill-Queen's University Press, 1990.