Viscious, Rude and Crude: Vinegar Valentines and Penny Dreadfuls

Not all Valentine cards once received were a warm welcome of sweet sentiments from your adoring admirer. If you were the unlucky recipient of a vinegar valentine, these cards expressed everything except love. Filled with bitterly sarcastic illustrations, these vicious, rude and crude sentiments that were meant to spike humor were so penny dreadful.

A day dedicated to love and romance, Valentine’s Day dates back to Roman times. The holiday dedicated to St. Valentine, a martyr who died for this faith in early Christian history, has little to do with the love and romance traditions we practice in modern times. A priest named Valentine defied imperial rule to perform marriages during the reign of Emperor Claudius. The Emperor wanted to wage war but is male subjects refused to leave their lovers and battle for their ruler. In anger, the Emperor forbade marriages and cancelled all engagements. Valentine found the order unreasonable and therefore performed secret marriages. Valentine was thrown into prison in 269 AD. Valentine fell in love with the jailor’s daughter and began sending her love notes signed, “From your Valentine”. Even though Valentine was beheaded, his sacrifice for love won him sainthood and a day named for him.

Relic of Saint Valentine in the church of Santa Maria in Cosmedin, Rome. The remains have lain since the 1700s. –

The practice of sending a valentine was embedded in the lover’s legends. Charles Duc d’Orleans is credited with sending the first valentine card. D’Orleans was a prisoner in the Tower of London in 1415 and sent love poems to his wife while he was held in confinement. The first commercially produced valentine was created in 1809 in England. By 1840 valentine cards comic valentine cards became all the rage during the Victorian era. Before valentine cards were commercially produced, they were made by hand-decorated with elaborate frills and flowers that carried sentimental significance.

An English Victorian era Valentine card located in the Museum of London. –

But the funny elaborate valentines took a savage turn between 1840 and 1910. Insulting valentines became popular and only cost a penny which became referred to as “vinegar valentines” or mistakenly called “penny dreadfuls”. Penny dreadfuls was a term that referred to a form of literary works known as dime novels with cheap sensational storylines and featured such characters as Sweeney Todd and became a part of pop culture among young people in 1890s Europe. The rude and crude hate mail was so dreadful, the cards were rarely signed but made their point. Vinegar valentines were introduced in 1858 by John McLaughlin, a Scotsman with a New York City publishing business. But what made these slanderous and downright offensive valentine greetings become so popular? Perhaps it was a reaction to the repression and stuffy morality of the Victorian era. Some of them were so vicious, the Chicago post office refused to deliver 20,000 cards calling them too vicious and obscene. But despite their barbarity, vinegar valentines became wildly popular.

Valentine, c 1909 – Missouri Historical Society

Lacking the ornate refinement of traditional valentine cards, the image they carried was designed to caricature the shortcomings of the recipient and encapsulated the spirit of the Victorian era.

Insulting sentiments in the card would contain such phrases as:

“You hateful, despicable wretch, you lie whenever you draw breath. Deceitful, cunning slandering devil, always trying to do evil. Beware that your lying tongue is not from your vile mouth wrung.”

Valentine, c 1875 – Royal Pavilion & Museums, Brighton & Hove

Despite the sting of cupid’s arrow, thousands of these mannerless missive cards were exchanged. In blaring colors, printed on an 8×10 sheet of cheap, rough paper, was an unflattering caricature of a “loudmouth”, “the big spender”, “the great athlete”, “the old maid”, and “hen-pecked husbands”. During the 1920s and 1930s, they were very popular among schoolboys who were more than happy to give their cranky teacher, their grouchy neighbor and bullish school girls. Every trade or profession was represented in terms far from flattering including politicians. These rivaling rude sentiments were popular for many years until around 1910 when public taste began to turn away from the vinegar valentines. It wasn’t until the 1950s that similar vinegar valentines hit the market again in the form of “offbeat” modern versions. The once nasty sentiments became bittersweet slams such as:

“Dear Valentine, I’ve grown accustomed to your face – it wasn’t easy”.


“Dear Valentine, Tell me, if you had it to do all over again, would you still fall in love with yourself?”

Very few vinegar valentines have survived because of their unsentimental flair, some recipients tore them up or even burned them. There are accounts from memoirs and newspapers that show fist fights, court cases, suicide and attempted murder that resulted from sending vinegar valentines. In 1885, the Pall Mall Gazette of London published a story about a husband who shot his estranged wife after she sent him a vinegar valentine. In 1847 and deemed the “fatal valentine” a woman in New York City overdosed on laudanum after receiving a vinegar valentine from a man who had led her to believe that he was interested. At one point, vinegar valentines were so popular they were blamed for taking over and ruining a once sacred, romantic holiday. When tragedy hit the newspapers, the tradition was perceived as having gone too far and gradually faded out.

“I’ll treat you with scorn whenever I pass, you deceitful, oily-tongued snake in the grass.”

Psychologists claim that people looking for relief from their pent-up frustrations and emotions sent vinegar valentines anonymous to relieve their impulses to violence by telling off their obnoxious teachers, nosy neighbors, and tyrannical bosses. Vinegar valentines reflected the spirit of the times between the late 1800s to 1920s with rising taxes, wartime, and the women’s suffrage movement. When vinegar valentines made a comeback in the late 1950s, they reflected housing shortages, the atomic era and rockets to the moon. The malicious vinegar valentines that used to break hearts and leave pillows wet the tears, faded into history with the moustache cups and the spinning wheel. Modern versions of vinegar valentines are milder in humor compared to the hideous insults that once flourished.

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Hope Thompson
Hope Thompson

Hope Thompson is the editor and publisher of Unmasked History Magazine. She has been a freelance journalist for seven years and has published articles for popular media websites such as Her focus has been on the hidden history, Native American culture, Appalachian and Southern folklore traditions.

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