Creating a positive classroom experience for students can be a challenge, especially when teaching a contested topic such as gender studies. Teaching and learning gender is teaching and learning against the grain, which can lead to feelings of comfort and discomfort among students. The objective is to capture different manifestations of dis/comfort and transformation within the classroom by presenting a case based on gender studies. The study builds on course evaluations collected between 2009 and 2019. The findings reveal three appearances of dis/comfort: inexplicit manifestations, explicit manifestations, and a transformation stage in which the experienced dis/comfort operates as a steppingstone leading to possible change through affective dissonance. We suggest that discomfort can be mitigated by openly discussing resistance and by giving students more autonomy over course assessment and lecture content but without watering down the curricula. Thus, it is possible to navigate transformation and reduce compliancy with the ruling regime.