Drawing on the first author’s (Matthew) research with male psychiatric ward security guards whom he worked with for 16 months, we discuss in this case study how bringing masculine status into semi-structured interviews produces gender relations and knowledges about men that would largely be inaccessible to researchers who are gendered outsiders. Matthew’s insider status provided participants with an extra layer of comfort to speak freely about their patriarchal beliefs, which involved positioning women and queer people in security work as risky and less worthy subjects, as well as favoring violence as a means to resolve issues with captive mental health patients. We reflect on the implications of questions changing during the research process, especially when the researcher has powerful feelings and positions on their research question as a result of their immersion. The ways in which Matthew performed gender had changed considerably from the time he was doing security work to when he conducted his interviews. We expose his interview dialogue and questions that led to the production of a visceral knowledge and analysis of the contentious perspectives on gendered violence that were shared. We conclude by emphasizing the role reflexivity and forgiveness play in helping the researcher develop a sense of closure and ability to view participants as allies, not enemies. This case study provides readers with techniques and points of reflection on how to mobilize their emotions and political subjectivities in interview settings to draw out the important tensions and divergences participants may share.