Many vinegar valentines from the mid to late 19th century were drawn by Charles Howard, who did absurd caricatures of the pitiful recipient in full color. An issue of Kindergarten Primary Magazine from 1895 worried about the moral implications of these cards for children. A teacher from Iowa wrote that she staved off the “desire to send vulgar valentines” by telling students stories from St. Valentine’s treacherous life. The magazine said that teachers must do what they could to help “make it a day for kind remembrance rather than a day for wrecking revenge.”
Some vinegar valentines were playful or sarcastic, but most could really sting. “Lady Shoppers” and salesmen were sent or handed vinegar valentines admonishing their values. Some vinegar valentines called physicians names like “Doctor Sure-Death” (a character who ran expensive bills), and others even poked fun at the “stupid postman” who was delivering the mail.