This article argues for conducting emancipatory narrative research with the explicit intent of transforming participants’ lives by opening up new subjective possibilities. Drawing from Megan Boler’s pedagogy of discomfort and Gubrium and Holstein’s active interviewing, a narrative research method called an inquiry of discomfort is proposed. An inquiry of discomfort emphasizes the proactive and transformative potential of research projects for both researcher and participant. The aim of an inquiry of discomfort is to identify and promote a beneficial shift from dualistic, categorical, and entrenched subjective positionality to a more ambiguous engagement with social reality. The argument is considered in light of preliminary empirical findings from a narrative pilot study of masculine heterosexual subjectivity in graduate education, conducted in the fall of 2003. Based on theoretical and empirical evidence, the general features of an inquiry of discomfort within an emancipatory narrative study are presented.