This article aims to identify the gender stereotypes conveyed by male teachers and male high school students in their stated perceptions of their teacher-student relationships (TSR). Using an interpretative qualitative approach, this study highlights the statements of 18 teachers and 86 boys in high school collected through three data collection strategies, namely the semi-structured interview, the focus group and the survey questionnaire. The qualitative data obtained were analyzed using the conceptualizing categories. The main results highlight that some teachers mention communication with boys is based on stereotypical male interests. In counterpart, some boys report the teachers being emotionally distant from them.