For pre-service teachers (PST) entering unfamiliar schools and communities, it is vital to get to know those communities for themselves. Within the “post-truth era” PSTs must interrogate false essentialist narratives and create counternarratives that reflect the complexity of communities in which they work. Drawing from critical aesthetic pedagogy (Medina, 2012) and positioning theory (Davis & Harre, 1990), this paper explores how PSTs in a Master of Arts in Teaching (MAT) program positioned themselves and the communities in which they were immersed throughout a month-long community portrait project. Findings indicate that creating multimodal, aesthetic representations of community facilitated an increased awareness of positioning and expanded notions of community resources for PSTs. Additionally, the collaborative act of curating portraits encouraged dialogic repositioning.