The newspaper advice column has shaped the American imagination in unacknowledged ways. Using Nathanael West’s Miss Lonelyhearts (1933) as a lens into a wily, underestimated genre, I juxtapose West’s riff on the newspaper advice column with readings of the real thing. I review the lovelorn column’s distinctive features and situate West’s satiric novella in that context. I also examine the racial dynamics of both the novella and the genre, touching briefly on the careers of two lovelorn columnists: the well-known Dorothy Dix, who was white, and the now-obscure Princess Mysteria, who was African American. In the process, I show that literary critics have allowed the misogyny of West’s novella to define one of the most enduring of all women’s popular genres. Advice columns have been dismissed as a morally bankrupt product of consumer capitalism, but they did more than simply render irrelevant the question of genuine emotional expression. Using a complex masquerade of gender and race, columnists shifted counsel outside the bounds of interpersonal exchange, forged an anonymous, recursive imaginative field, and generated glimmers of an ethics of intimacy.