Vinegar Valentines – unflattering Valentine’s Day cards from anonymous haters

Vinegar Valentine, circa 1900 / Public Domain

Vinegar valentines were a type of insulting cards. They are decorated with a caricature, and featured below an insulting poem. Ostensibly given on Valentine’s Day, the caricature and poem is about the “type” that the recipient belongs to—spinster, floozy, dude, scholar, etc. They enjoyed popularity from the 1840s to the 1940s. These cynical, sarcastic, often mean-spirited greeting cards were first produced in America as early as the 1840s. Cheaply made, vinegar valentines were usually printed on one side of a single sheet of paper and cost only a penny.
The unflattering cards reportedly created a stir throughout all social levels, sometimes provoking fisticuffs and arguments. Ironically, the receiver, not the sender, was responsible for the cost of postage up until the 1840s. A person in those days paid for the privilege of being insulted by an often anonymous “admirer.” Millions of vinegar valentines, with verses that insulted a person’s looks, intelligence, or occupation, were sold between the 19th and 20th centuries.
info WIKIPEDIA

Vinegar Valentine by Raphael Tuck, dated 1906 / Public Domain