by Randal C. Hill
It may seem hard to believe, but once upon a time, nearly half of all Valentine’s Day messages sent contained grotesque caricatures of the intended recipient and mean-spirited, hurtful notices intended to drive in the knife.

By the 1840s, people in both England and America were creating Valentine’s Day missives of heartfelt poetry, often illustrated by elaborate flourishes and mailed in quilted-paper cards bound in festive ribbons. Improvements in the printing process and paper production heralded a boom in the sale of mass-produced valentines.
Then things began to change. It started quietly, a ripple that gradually swelled into a tidal wave. Some pranksters had enjoyed mailing valentines that involved gentle teasing—a little joke here, a little poke there—meant to produce a smile. But, over time, the mood of such messages soured and slowly turned increasingly crass. Sent anonymously, such vitriol could easily sting with insults that would normally never be spoken to another’s face.
These “vinegar valentines” were the popular evil twin of the traditional, positive gesture. Printers, of course, were delighted with the extra revenue, and produced the penny-a-piece cards on cheap, flimsy sheets of paper, folded, and sealed with a dab of wax. Cards could be mailed without a stamp, which meant that someone receiving such cruelty would also have to pay the postage (also one penny) before reading the snarky contents.

Anybody, it seemed, could be considered fair game—neighbors, relatives, employers, friends and colleagues, people from all walks of life and placement on the social hierarchy. Sometimes the cards targeted unwanted suitors, but many others made fun of one’s age, weight, looks, occupation, or marital status, as well as any number of human foibles.
One often-maligned group was the suffragettes, women attempting to secure voting rights:
Your vote from me you will not get
I don’t want a preaching suffragette.
But sometimes the mailers (assuming that the original sender could be identified) got their comeuppance, as a popular retort might simply be a terse but powerful threat:
No vote, no kiss – So take that, fella!
In time, people tired of the relentless negativity, and vinegar valentines slowly disappeared, giving way to “normal” February 14th cards that featured positive communication. Today, collectors of 19th century ephemera have little trouble in locating traditional Valentine’s Day cards, but finding surviving vinegar valentines is much more difficult, as resentful recipients usually burned them after reading.