Examining the still underexplored elements in educational theorist Paulo Freire's work, this essay begins from his claim that problem-posing pedagogy works as a "kind of psychoanalysis." Situating Freire between the critical philosophical and psychoanalytic traditions, Alex Armonda offers a new reading of the problem-posing dialectic, mapping parallels between Freirean pedagogy and psychoanalysis on the nature of the subject/object relation, while thinking new connections across the philosophical-analytical divide on questions of being, subjectivity, and politics. First, he discusses the onto-epistemic specificity of "the human" in Freire and situates it in relation to the split subject of the unconscious in Lacanian psychoanalysis. Second, he presents the subject/object encounter in Freire, demonstrating that a similar notion of the unconscious informs Freire's account and plays a central role in his understanding of the banking and problem-posing pedagogical experiences. Advancing a Lacanian reading of the problem-posing encounter, Armonda concludes by reflecting on key differences between the dialectical-materialist and psychoanalytical interpretations of Freire, and how the latter opens new perspectives on "reality" as an inconsistent space of contest, generating alternative ways of conceiving political subjectivity and the possibility of radical social transformation in the present.