This chapter examines the decline of the brothel as a commercial form in the latter decades of the nineteenth century and the recasualization of sex work in the context of women’s changing labor arrangements and the growth of urban leisure culture. Baltimore’s brothels, in keeping with patterns in other US cities, lost their prominence as a sexual labor arrangement as the result of changing land use patterns, new styles of courting, and evolving work and housing arrangements for young laborers. With the rise of new types of urban leisure, young women who sold or traded sex increasingly resorted to concert saloons, dance halls, and amusement parks to solicit men and to furnished room houses to carry out their trysts. Once-taboo forms of sexual exchange became incorporated into the courting and leisure culture of young working people. Brothels, which in many ways reflected an outmoded, domestic model of courtship, had to embrace niche sexual markets in a struggle to compete for labor and customers.