In this chapter, some historical background is presented to the current research on gendered violence and harassment in educational institutions. The focus of the analysis is the fine line between gendered play and harassment in schools. The method was to present the main parts of an earlier article that draws on ethnographic data from lower secondary schools in Helsinki in the 1990s and life history interviews with the same young people a few years later. The second part of the chapter suggests interpretations of changes and continuities, using more recent documents and research. The main conclusion is that the overall patterns have not changed significantly, and the stories told in the article could take place today. The complexity of harassment or violence is evident in the varying interpretations of the incidents by the young women, the perpetrators, the teachers, and the researchers. Moreover, an action can be perceived as a joke while it is happening, but as humiliating later on. Despite overall patterns not having changed very much, it is possible that cyber-based harassment is a new challenge. A challenge for schools and teacher education is still today how to address harassing behaviour, where to report it and how to prevent it, together with students.