Lickable Cities is a research project that responds to the recent and overwhelming abundance of non-calls for gustatory exploration of urban spaces. In this paper, we share experiences from nearly three years of nonrepresentational, absurdist, and impractical research. During that time, we licked hundreds of surfaces, infrastructures, and interfaces in cities around the world. We encountered many challenges from thinking with, designing for, and interfacing through taste, including: how can and should we grapple with contamination?, and how might lickable interfaces influence more-than-humans? We discuss these challenges to compassionately question the existing framework for designing with taste in HCI.