How Vinegar Valentines Infused Love Letters with a Bitter Twist

February 14th, 2024

“Pity a Poor Wounded Heart”, vinegar Valentine’s card, circa 1875. Public domain image (detail)

Valentine’s Day is upon us- the day of love and romance. Americans send out an estimated 145 million Valentine’s cards annually- in an industry valued at $20 billion. Yet, despite its modern relevance, the original festival- or feast- of St Valentine has a curious history.

The two legendary saints associated with that particular day, both date from the 3rd century and seem to have no connection with love- although the historical details are decidedly sketchy. Saint Valentine of Rome, the patron saint of beekeepers (and later the patron saint of lovers), is said to have cured the daughter of his jailer from blindness and was martyred for his faith on February 14, 269 AD. Curiously, a second Saint Valentine, a Bishop from Terni in Italy, is supposed to have been martyred on the same day: some historians think that the two saints may be the same person. But in 496 AD, the Papacy established February 14 as the Feast of Saint Valentine- and we’ve never looked back.

Dr. František Ehrmann, Saint Valentine is healing an epilepsy, circa 1899. Public domain image

By the late Middle Ages, with its ideal of courtly love, the tradition that Valentine’s Day heralded the first day of Spring took hold, and with this idea came the notion that birds mated on that day. In his 14th-century poem, Parlement of the Foules, Geoffrey Chaucer writes how birds gathered to mate on ‘seynt valentine’s day’. Certainly, by the 18th century, couples exchanged flowers, candy, chocolates, and hand-made tokens- and these earlier valentines make desirable collectables. In November 2016, a framed Valentine inscribed in ink with verse, birds, love hearts and naive figures in 18th-century dress- formerly in the collection of The Colonial Dames of America, sold for $2,000 at Freeman’s, Philadelphia. And in 2019, a hand-drawn Valentine, dating from 1790, sold for a remarkable £7,192 at Hansons of Derbyshire, the British auction house.

The world’s oldest Valentine card, dated 1790, sold at Hansons of Derbyshire in 2019. Image © Hansons

But by the 1840s, the invention of the affordable, pre-paid postage stamp meant that love-sick hopefuls could send anonymous cards to their romantic crushes. By 1841, the newly reformed British postal system coped with as many as half a million Valentine cards and in 1846 alone, over 30,000 valentines passed through the New York City post office in a single day. Advances in printing also reduced the cost of printed cards. In 1847, Esther A. Howland, an enterprising artist and entrepreneur from Worcester, Massachusetts, began selling some of the first commercially produced, or mass-produced, Valentine cards.

Howland’s bookseller father initially sold Valentine cards imported from England. Esther took this idea and quickly built a thriving business, employing young women to make her cards at home, using pretty paper scraps, tinsel, ribbons and lace. Esther deliberately priced her cards as luxury objects, selling some for as much as 75 cents a piece- a considerable sum. The New England Valentine Company (NEVC) remained in business for thirty years, with estimated annual sales in the region of $50,000-75,000 a year- a remarkable achievement. In 1880, Howland sold her business to a competitor, George Whitney, and the George C. Whitney Company continued to prosper until 1942, when wartime paper shortages caused its liquidation. Esther Howland- ‘The Mother of the Valentine’- died unmarried in 1904.

Left: Cloth and lace Valentine card made by Esther Howland, ca. 1870s. Public domain image | Right: Valentine Card by Esther Howland. Image Wikimedia Commons / Licence CC BY-SA 4.0 DEED

Esther Howland’s cards are delightful, avidly collected by ephemera enthusiasts, and recognized by the red ‘H’ stamp to the top left corner of the back page- a device Howland used to distinguish her cards from her rivals. The Metropolitan Museum of Art holds several Howland cards in its collection, all typical examples of her work, with cut-out scroll work superimposed against colorful backgrounds in red, yellow, pink and green, embossed gilt and printed lithographic cut-outs depicting cherubs, roses, and song-birds. Although produced in large numbers, Howland’s cards can be valuable. In 2018, an especially beautiful example with the words ‘Token of Love’ hidden beneath ‘pop-up’ lace decoration and chromolithographic prints of love hearts and butterflies sold for $450 on eBay. This card- seemingly in excellent condition- was from Howland’s later production period, with the red ‘H’ stamp printed on the bottom.

“Pity a Poor Wounded Heart”, vinegar Valentine’s card, circa 1875. Public domain image

Unfortunately, Valentine Mania also produced a backlash, creating the ‘Vinegar’- or ‘Reverse’- Valentine. The Vinegar Valentine was a humorous or offensive card, often a comic caricature accompanied by a coarse ditty, limerick or poem, sent anonymously to an innocent victim the sender disliked. During the second half of the 19th century, many thousands of Vinegar Valentines were sent out in Britain and the United States, received by unfortunate men- and women too: a bit like a 19th century ‘troll’- similar, in a way, to the dark side of our own social media today. A middle-aged man might be teased for his baldness, an older woman accused of being a gossip, or a young girl a shameless flirt.

A “Vinegar Valentine” for a “Simpering Miss”. Public domain image

The earlier Vinegar Valentines- dating from the 1860s- are rarer and harder to find- as, unsurprisingly, many of the unlucky recipients threw them away- and who can blame them? Some of these Valentines are really unpleasant: crude, simple affairs of a reasonably large size, printed on cheap paper, folded in the centre (to be sealed with wax), and illustrated with mocking lithographic caricatures.

An 1870s “Vinegar Valentine” where the sender declares that she would never marry a superficially-attractive male “snake” who would make her miserable as a wife. Public domain image

One card accused a man of being a ‘Society Idiot’, accompanied with a caricature of a monocle-wearing gentleman in striped pants, and the ditty: ‘You go in good Society, or at least, you say you do / In fancy clothes you love to shine / But heads that run so much to nose, have little room for brains! ‘ This card sold on eBay for $150 in 2022. Another card encourages a young man to ‘commit suicide’ by smoking ($100, eBay 2022). And a card in the collection of the Victoria & Albert Museum in London depicts a young man as ‘A Snake in The Grass’. According to Ruth Webb Lee, author of ‘A History of Valentines’ (1952), by the mid-19th century, vinegar valentines represented about half of all valentine sales in the United States.

“Vinegar Valentine” for your local saleslady, 1910. Public domain image

But by the late 19th century, Vinegar Valentines had fallen out of favor- at least in Britain, with The Graphic (February 17 1894) reporting: ‘St Valentine’s Day attracts very little attention nowadays in England, but across the Atlantic, the Saint is still honoured’. And after the Second World War, Valentine’s Day underwent a significant revival- influenced, in part, by America’s commercial card manufacturers. These days, Valentine’s Day is big business- and the trend continues unabated, with no sign of decline. Cynics sometimes complain of a commercialization, but we are, at least, spared the misery of the Vinegar Valentine. That one’s best left to the collectors.

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