In stark contrast to sentimental valentines, which are in many ways similar to the valentines used in current celebrations of the holiday, vinegar valentines demonstrate that anonymous mean-spirited messages long predate the advent of the internet.

The manufacturer of this cruel valentine is McLoughlin Bros. of New York. The company also printed elegant, richly-colored children’s books comic almanacs, games, and blocks. The crude visual appearance of this valentine is thus clearly purposeful, as it magnifies the meanness of the message. Selling for about a half penny or a penny, these cheaply-made images were more likely to have been quickly thrown away than tenderly preserved by their recipients. They confirm simultaneously the ephemerality of nineteenth-century industrial print culture and the persistence of human cruelty.

The caricature and verse of the following comic valentine are especially vicious. The term "spooney" is defined as a simple, foolish person. In some cases, as in this other vinegar valentine, spooney was used simply to deride an overly sentimental person. In this case, however, it seems that the term may have racial connotations. The black featureless character with wide white eyes and bushy uncombed hair resembles depictions of black people that stretch at least as far back as the creation of the Jim Crow minstrel character in the 1830s, and became more exaggerated over time. Another early example of this trope is this 1830s sheet music cover. While perhaps not directly connected to minstrel shows and blackface performances, an increasingly popular form of entertainment beginning in the early nineteenth century, the dark complexion of the figure reinforces dominant cultural assumptions that African-Americans were simpleminded and foolish. These assumptions lasted beyond the Victorian era; we can see similar expressions of this prejudice in twentieth-century sources, such as in Irving Berlin’s use of "spoony" alongside "coony" in his 1909 song “Wild Cherries”.