Resumo: This article aims to discuss the consequences of simulating the individual’s experience with out-of-home advertising through a computer screen. It means, it is an essay focused on the debate and reflection about applying digital narratives as resource to preserve, to explore and, even, to optimize our relationship with this kind of media (so related to the city space). There is no intention to replace any real world action, but yes to preserve it (memorizing the past), to understand it (studying the present) and to optimize it (testing the future) by the digital ways. In resume, the work launches a tecnoliberal thought, because it looks to new technologies as a potential instrument to improve our relationship with the city space. The debate goes beyond theoretical references (Baudrillard, 1994, Negroponte, 1995; Kerckhove, 1995; Castells, 1999; Lévy, 1999; Virilio, 2000, Manovich, 2001; Jenkins, 2003; Mesquita, 2006; Viana, 2009; Martins, 2010; Zagalo, 2010; Pires, 2010; Zilles Borba, 2013) when makes use of a specific digital prototype, developed by the authors as part of a doctoral degree program about the virtual reality transposition of the physical communication experience among observer, advertising and urban space. On this way, as basis for extracting qualitative data, this digital model is empirically investigated. As a walker who observes billboard images in the streets, the authors carried on an exploratory observation, which was fundamental to get the receptor feelings in the synthetic scenario and, in consequence, to reflect about the paradigm of time, space and materiality in technological simulations. We do underline those three example: a) preserving ephemeral images which do reflect cultures, costumes and technologies of the people in some time of History (with binary technics); b) exploring the advertising in a digital model who allows to visualize the city space through the avatar’s eyes (with visual, graphics and immersive technics); and c) optimizing the communication experience by testing and researching variables in the virtual world before applying it in the physical one (design and programming technics).