This chapter explores the reflexive activity of participants in the gay sexual marketplace with a focus on the websites and apps designed specifically for sexual and intimate networking. I want to suggest that a pragmatist approach to markets and market devices has the potential to move us beyond the critical impasse of sexual commodification—so often levelled at digital sex—to enable a more constructive engagement with the design of sexual networking services on the part of sex researchers and service-users. Online hookup apps and websites are producing new sexual subjectivities, cultures, and practices among the growing number of men around the world who use them to seek connections with other men. Now operating as the most common way men search for and meet intimate partners in many locations, these devices have become part of the infrastructure of sex and intimacy for many men who have sex with men around the world (Race, 2015, 2018). As a result, gay cruising is taking new forms, assuming new genres and proceeding through new avenues—practices that are largely mediated by the design and affordances of gay sexual networking services. Following Callon and colleagues (2002), this article explores the sense in which the digital sexual marketplace “evolves, and . . . becomes differentiated and diversified” because actors in the digital economy (including tech developers and service users) “are caught in a reflexive activity: the actors concerned explicitly question their organization and, based on an analysis of their functioning, try to conceive and establish new rules for the game” (Callon et al., 2002, p. 194). In other words, these market actors are engaged in activities of “problematization” (Foucault, 1985)—a concept I will elaborate in further detail below. My suggestion is that the reflexive and experimental character of these activities provides some basis for constructive collaboration between sex researchers, tech developers, and consumers on how best to design, organize, and enact the sexual marketplace.