Wild pedagogies invites educators to engage with more-than-humans as co-teachers and co-researchers. In collaborating with city grass, this paper blends rhizomatic thinking, literary ecocriticism, and the rewilding of pedagogy within severely constrained circumstances. Citing cognitive, emotional, and physical benefits of engaging with free and flourishing nature, this research asks: How can the severe constraints of particular sociopolitical circumstances and disciplines, such as postsecondary literature courses, be creatively encountered to support engagement with flourishing more-than-human kin? It also asks: What would grass do? This paper walks readers through many barriers faced by city college humanities courses and suggests practical, creative work-arounds that, while focused on college literature classes, can be adapted to educators in diverse disciplines and contexts. Because we need playful thinking to think creatively — even on the brink of catastrophes — this paper is written as a choose-your-own adventure game. Educators will be invited to consider the institutional, geographic, academic, political, personal, and social barriers impacting their pedagogical choices. Ecologically concerned educators need pragmatic, creative, and compassionate support to envision how wild pedagogies pathways can be applied to their course loads. Here, these explorations are designed to be experiential and experimental, open-ended, and ultimately mutually liberating.