Nothing says Vinegar Valentines like: “Everyone thinks you an ignorant lout.”
People sent Vinegar Valentines as far back as at least 1840. Back then, they were called “mocking,” “insulting,” or “comic” valentines—“vinegar” seems to be a modern description.
They could be sent to neighbors, colleagues, and members of the local community as well as to wanted and unwanted partners. They often featured garish caricatures of men like the “Dude” or women like the “Floozy.”
The nasty valentines were produced by the same companies as the lace-and-roses kind. At a penny a piece and a penny for postage, they were affordable insults.
Vinegar valentines could be lightly teasing or truly nasty—such as those that suggested the reader commit suicide.
Some warded off unwanted suitors, while others made fun of people for drinking too much, putting on airs, or engaging in excessive public displays of affection.
There were cards telling women they were too aggressive or accusing men of being too submissive, and cards that insulted any profession you could think of—artist, surgeon, saleslady, etc.
In Civil War Humor, Cameron C. Nickels wrote that vinegar valentines were “tasteless, even vulgar,” and were sent to “drunks, shrews, bachelors, old maids, dandies, flirts, and penny pinchers, and the like.”
He added that in 1847, sales between love-minded valentines and these little notes of in-affection were split at a major New York valentine publisher.
By the mid-19th century, vinegar valentines represented about half of all valentine sales in the U.S.
Yet not everyone was a fan of these mean valentines. In 1857, The Newcastle Weekly Courant complained that:
“the stationers’ shop windows are full, not of pretty love-tokens, but of vile, ugly, misshapen caricatures of men and women, designed for the special benefit of those who by some chance render themselves unpopular in the humbler circles of life.”
One of the famous artists working in the Vinegar Valentine genre in the late 1800s and into the 1900s was Charles Howard, who was with the McLoughlin company.
According to Nancy Rosin, president of the National Valentine Collectors Association: “He was very depressed about it….He felt he was inflicting pain on people.”
Ironically, the receiver, not the sender, was responsible for the cost of postage up until the 1840s. A person in the very early days paid for the privilege of being insulted by an often anonymous “admirer.”
In later days, the more surly cards weren’t always welcomed by postmasters. About 25,000 valentines were held in a Chicago post office for being unfit to send, due to the many rude and vinegar valentines in the haul.
We don’t know how many of them were sent as a joke – or how many were meant to harm. It’s clear that some people took their message seriously.
In 1885, London’s Pall Mall Gazette reported that a husband shot his estranged wife in the neck after receiving a vinegar valentine that he could tell was from her.
Scholar Annebella Pollen also says there was a report of someone committing suicide after receiving an insulting valentine—not completely surprising, considering that’s exactly what some of them suggested!
The instinct to anonymously shame fellow members of society dates to a much earlier time. In 16th-century England, for example, townsfolk in masks, beating pots and pans, might converge on the house of someone they believed to be guilty of adultery.
Contemporary trolls bash and belittle via the Internet.