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In early 2019, we developed a workshop that examines changing representations of masculinities and femininities through advertisements from today and from 30 years ago. We employ a pedagogy of discomfort (Boler, 1999) and challenge participants—whether students, teacher candidates, or seasoned educators—to historicize and critique how they co-construct sociohistorical representations and performativity of gender (Butler, 1990). Our hopes are that participants begin deconstructing how and which understandings of gender became normalized to them, as well as how they perpetuate or disrupt “masculinities” and “femininities”. Through regular debriefing, we realized that we do not merely facilitate but also actively participate in each workshop, not just guiding but also being guided by changing discussions with every iteration, suggesting needs to historicize and critique our own discomforts in relation to participants’ engagements. In identifying and reflecting on ‘critical moments’ from our workshops, we conducted a collaborative autoethnography (CAE) to examine not only how participants responded to our call for unpacking their representations, but also how participants caused us to challenge our own representations. In using CAE, our experiences and reflections became our data, and we analyzed interpretations of experiences for commonalities and differences, creating opportunities to deconstruct our relationalities in constructing and historicizing representations (Hernandez, Chang & Ngunjiri, 2017). In this article, we discuss how this process affected the workshop’s evolution and our continued self-analysis. We argue that if students are to interrogate sociohistorical gender constructions, educators must continuously examine how their own discomforts influence their engagement with students’ responses.