Embracing a critical pedagogy of play, this paper explores how first-year architecture students can be introduced to the sociocultural complexity of contested urban environments, while simultaneously cultivating their imaginative and creative skills. The pedagogical method adopts play as a colearning tool and situated design methodology to activate spatial performativity and foster community engagement for collectively reimagining spaces of coexistence within contested urban contexts. By positioning play as a critical and exploratory mode of engagement, students can begin to apprehend and interrogate the complexities of urban space through embodied, situated, and imaginative practices, fostering an educational culture that nurtures civic-minded architects.