In the last decades of the nineteenth century, intimate affairs flooded into the expanding classified pages of the mass press. Marriage, sexuality, romance, pornography, and hygienic services and goods were offered or requested in long columns of text-based ads. This article analyzes the motivations and mechanics of this much-contested commodification of the intimate, marked by the uneasy meeting of market and morality. Indeed, the relationship between the press and the ads that appeared in its pages was an ambiguous one in which opportunistic pragmatism and efforts at moral control coexisted. The study of these « intimate » ads reveals the emergence of forms of self-expression in which the publicly unspeakable became speakable as advertisers communicate about private matters while abiding by the rules of public engagement.