In this paper, we investigate how everyday playfulness can create opportunities for agonism. Playfulness and agonism have only rarely intersected in HCI research, such as using game design elements in Agonistic Participatory Design, or proposing agonism as a theoretical foundation for Political Play. Building on these foundations, our work aims to broaden the design space where playfulness and agonism meet. Drawing on methods from Situated and Emergent Play, we created a design intervention that prompted reflection and empathy among participants, while establishing a shared understanding of the latent conflict the intervention aimed to address. Based on our findings, we propose considerations for designers seeking to use playfulness to create opportunities for agonism. Grounded in Situated and Emergent Play, we furthermore contribute the method of tracing frictions, which offers a new avenue for designing at the intersection of playfulness and agonism.