This article focuses on the birth of social networking and digital recommendation technologies and their relationship to current cultures of postfeminism and neoliberalism. These technologies, primarily designed to bring users in touch with other people and consumer goods, are tied to larger cultural movements focused on equating greater consumer choice with greater freedom. Most popular histories of these technologies portray them as being created primarily by and for men, but many of these technologies were actually pioneered by Pattie Maes, a professor at the Massachusetts Institute of Technology (MIT). In the MIT Media Lab, Maes created various programs, including one that could automatically schedule meetings for users, one for prioritizing and sorting e-mails, one of the first matchmaking programs, and Firefly — one of the first online social networks, if not the very first. By focusing on these projects and Maes's reasons for creating them, I will show how they both respond to and further constitute the gender politics of postfeminism.