Relationships in the city are much about economic transactions and market exchange, as scholarship about the urban amply documents. Drawing on a film that follows the precarious possibility of sleep in Delhi, India, this essay recognizes the work of ‘sleep entrepreneurs’—ordinary people who offer sleep for a price. Vignettes from Delhi illustrate the theme of empathy in the city as it is pursued here—framed differently from dominant discourses of prescribed care in the city. Viewed as a small motif of life-affirming relationships, these transactions suggest the potential of exploring the city and the urban condition as generative of relationships that are not often analyzed.