Generation Z (Gen Z) represents something of a quintessence for the broken promises that now seem to make up the promise of higher education. But if despair indicates the dark side of generational malaise around things like civic engagement, community, and student learning, the dark humor that has emerged out of these generations points to modes of democratic citizenship that are more about reconciliation than resignation. This essay offers a critical reflection on Gen Z humor, its place in college and university classrooms, and its usefulness as a resource for reconsidering how teaching and learning might be tied to a comically examined life. It proceeds with a fresh look at pedagogies of hope as developed by Paulo Freire, Martha C. Nussbaum, bell hooks, Henry A. Giroux, and others. This examination allows for the conceptualization of a comic poësis for understanding how instructional practices that meet students on uncommon ground contribute to the production, creation, and care for personhood as well as public culture. Ultimately, this essay balances theories of a comic teaching praxis with actual activities from the classroom to meditate on a pedagogy of reconciling curricula with who and where students are, beginning and ending with feedback loops.