This chapter aims to present knowledge about teenage boys’ experiences of singing together in school. The study that the chapter is based on uses a phenomenological, gender theoretical and music didactic perspective. Earlier research shows that singing is practiced, and anticipated to be practiced more often by girls than boys in Western societies and schools. An analysis of interviews with the student Andreas and his music teacher Victor is presented, as they explore co-singing in a music profiled class in elementary school. The interviews were performed in 2013 and 2020, and analysed and presented as a «life story». It entails Andreas’ journey from being a teenage boy who refuses to sing in school to becoming a teenage boy who sings, and the role that Victor, as a music teacher, plays in Andreas’ journey. The chapter shows several gendered and pedagogical aspects in Andreas’ situation that influence him to at first mime and later on sing during choir lessons – especially the perception of singing as feminine coded and singing knowledge in choir.