Through the thematic analysis of a set of flash fiction stories published by the “Santiago in 100 Words” (Santiago en 100 palabras) literary competition, held in Santiago de Chile since 2001, in this article we discuss the ways in which city inhabitants face the contemporary urban life. The idea of dealing with the city is conducive to describe the problematic relationship that city dwellers have with their urban space. The notion of repertoire enables a global understanding of all the different expressions that this experience adopts. As a conclusion we propose, first, that the ways of dealing with the city adopt three typical ways in flash fiction stories. Second, that the flash fiction stories reveal a causal sequence in the way they subjectively experience the problems of urban life. Third, the production of urban and imaginary representations adopts an aggregative way that seems plausible to extrapolate to other areas.