With the question of what is between psychoanalysis and pedagogy, this essay presents a psychoanalytic frame for thinking about the study of uncertainty in teaching and learning from the vantage of the education of the author and her notion of “difficult knowledge.” I review my body of research through these dilemmas to picture a theory of learning curious about the fate of uncertainty and affected by the object of study namely, the human subject of education. Two problematics are explored: the theoretical impetus for representing a learning matrix through the vicissitudes of uncertainty, and second, commentary on an affected research. The essay suggests a research and writing style that returns to what could not be known from the immediacy of felt experience and that only later can be narrated as a story of the disparities, accidents, vacillations and fragmentary impressions that come to compose the problem that education as an emotional situation and as such difficult to know.