This project looks at the mutually imbricated relationship between space, sex, and technology in cultural output from the last fifteen years. Through an examination of sexual cruising cultures in Samuel R. Delany’s essays Times Square Red, Times Square Blue and John Cameron Mitchell’s film Shortbus, I unpack the ways in which technology is represented as a facilitator and barrier to the formation of spaces that foster queer sexual interactions. This thesis is interested in the ability of different technologies and spaces to promote the formation of heterogeneous relationships that cross categories of social difference—including race, class, and sexuality—following the HIV/AIDS crisis. Alongside an investigation of the potential of technologies of affiliation to support these kinds of interpersonal contacts, I argue that representations of technologically mediated intimacy are often limited to a hesitant ambivalence due to a cultural unease about the new types of non-normative relation offered by technology.