When should instructors encourage students to work across ideological differences and within unjust institutional structures in order to affect change? What are the dangers and challenges inherent in working across seemingly intractable differences in the community? And what is the value of such a pedagogical approach? The scholarship on feminist pragmatism, wicked problems, and democratic deliberation offers a set of tentative answers--a means forward--for instructors wrestling with these questions. In this article, Danielle Lake argues that the integrated application of insights from thinkers such as John Dewey and Jane Addams provides instructors with flexible tools that can empower students and foster place-based systemic change. The recommendations presented here emerge through the integration and the application of their philosophical ideas in place-based community engagement efforts with undergraduate students. In place of prescriptions or standardized formulas, Lake presents tentative observations, piecemeal strategies, and practical tools. In particular, she emphasizes the need for mutuality and reciprocity, narrative and perplexity, relationship building and cooperative action, as well as the expansion of our ethical framework in community-based learning practices. Instructors could, for instance, do more to invite others in--and to get out of--the classroom, to broaden their scope, to engage dialogic tools, and to privilege relationships. Collaborative, tolerant activism can create critical spaces for engaging the tension within difference, supporting reflexive action subject to comprehensive oversight. By exploring the value of a hybrid feminist pragmatist approach to engaging across divisions, as well as its dangers and challenges, Lake ultimately offers strategies for mutual and transformational change.