In this essay, Gerardo R. López, a non-undocumented immigrant scholar, who has done extensive research with undocumented immigrant communities, has a conversation with Alonso R. Reyna Rivarola, an undocumented immigrant scholar with Deferred Action for Childhood Arrivals (DACA), who writes and researches issues of how undocumented immigrant students experience schooling from a critical situated stance. Their conversation explores a range of topics that interrogate the problematic nature of researching the self/other, while simultaneously examining the broader purpose(s) of research in the academy.