Valentine’s Day began as a memorial to a Third Century saint who comforted captive Christians waiting for public torture by the Romans. Now this late-winter holiday is a day for Brach’s conversation hearts, frilly cards, and overpriced chocolates. Saint Valentine isn’t the only tradition we’ve shelved.

A century ago, Valentine’s Day featured another bizarre and sometimes cruel feature, which you’d set aside ONLY for those deserving your “special” disgust. These “no sugar and all spice” sentiments were called Vinegar Valentines.

The Era of the Vinegar Valentine 

Historians have traced these valentines as far back as 1840, where they were immensely popular both in England and the United States (the British called them “mocking valentines”). Usually these loveless notes contained satirical poems and drawings poking fun at a recipient’s looks, intelligence, reputation, or poverty. The insults ranged from a friendly, well-meaning ribbing to Don-Rickles-on-speed cruel. Here’s a quick sample of a vindictive Valentine:

Dang. How ’bout some Neosporin with that STING?

As cruel as they were, vinegar valentines were no rarity. In fact, when Valentine’s Day began to grow in popularity and commercialism during the Victorian Era, these nasty notes were just as popular as traditional valentines. Barry Shanks, an author and professor of comparative studies at Ohio State University, wrote “[Vinegar valentines] were a part of the valentine craze from the earliest years of its commercialization.”


The “joke” behind these valentines was as much practical as personal. In the mid to late 1800s, American post offices required the recipient of the valentine, not the sender, to pay for delivery. For a single penny, you could get a printed copy of a beautifully-illustrated insult, send it to someone deserving, and then have them pay for the libelous sentiment. No wonder they were so popular!

Trolling 150 Years Before Twitter

The popularity of these cards surprised even their printers, and the public soon stopped laughing as the cards became more frequent and darker in their content. The complaints never affected sales, and in both England and America, vinegar valentines profits eclipsed traditional ones. As with modern trolling, people took advantage of the ability to hurl anonymous insults with these inexpensive cards.

There’s no single documented reason for the fading popularity of these cards, which were all but extinct by World War II. Printing costs did increase. By 1930, it cost almost ten cents to purchase and mail a vinegar valentine, enough money to buy a small loaf of bread. The postal service also stepped in and to weed out the worst of the cards, deeming their offensive content “unfit to mail.”

It’s a century-long tradition that has not been picked up again; online trolling in social media now carries the mantle. A 2014 study from the Pew Research Center reported that 40% of adults have been targets of cyberbullying or trolling within the previous year. Since then the problem has only become worse. It seems that vinegar valentines didn’t exactly disappear, just morphed into a digital format that can be “enjoyed” all year long

Want to Know More? 

I steer away from those junk list articles, but “27 Victorian Era Vinegar Valentines” is worth checking out. A nice cross-section of this cultural phenomenon.

BBC Radio published a nice study of these insulting valentines, “Eight Incredibly Offensive Victorian Valentines,”  including an interview with historian Annebella Pollen.