–Photo Credit Missouri Historical Society

Valentine’s Day cards were not always sentimental. In the 19th century, as many as half of the valentines mailed in some places were not love notes at all but anonymous insults. 

By the 1840s, in both England and the U.S., the holiday was already taking on familiar trappings. People exchanged cards filled with romantic verse, often decorated with ornate flourishes on quilted-paper cards tied with festive ribbons. As printing and paper production improved, mass-produced valentines became widely available, making it easier and cheaper to send a message of affection.

Some early jokesters mailed teasing valentines meant to provoke a laugh, a gentle jab among friends. But over time, the tone of the messages soured. The jokes became cruder. And because the cards could be sent anonymously, the sender could say things they would never dare say face to face.

These mean-spirited messages became known as “vinegar valentines,” a bitter counterpart to the traditional valentine. Printers had little reason to discourage the trend. The cards were cheap to make, often printed on flimsy paper, folded and sealed with a dab of wax. Sold for a penny, they were easy to churn out and profitable in volume.

In the mid-1800s, the cruelty sometimes came with a second sting: Mail could be delivered without a prepaid stamp. That meant the recipient had to pay the postage before reading the message. In other words, you could be billed for your own insult.

Anyone could be a target: neighbors, relatives, employers, friends, colleagues. Some cards were aimed at unwanted suitors, but plenty mocked a person’s age, weight, appearance, occupation or marital status. Others latched onto whatever flaw or insecurity the sender could exploit.

Suffragettes, women pushing for the right to vote, were a frequent punching bag. One vinegar valentine might sneer:

Your vote from me you will
not get,

I don’t want a preaching
suffragette. 

But recipients and their allies sometimes fired back, especially when the sender could be identified. A popular retort made the stakes clear:

No vote, no kiss

So take that, fella!

Eventually, the appetite for spite wore thin. Vinegar valentines dwindled and mainstream February 14 cards returned to sweeter themes.

Today, collectors can easily find traditional Victorian valentines, but surviving vinegar valentines are harder to come by. Many recipients destroyed them as soon as they were read, either burned or tossed away.

Still, the impulse behind them never fully disappeared. The modern equivalent thrives online, where anonymity can once again embolden people to bully, insult or threaten with little fear of consequences. It is an ugly echo of a forgotten Valentine’s Day tradition and a reminder that not every message sent in the name of love is loving.