This chapter understands masculinity and its relation to homophobia as a process that moves from a focus on individuals and psychologising towards an understanding of the relationships that connect between individuals and contexts. It situates homophobia and investigates some central areas and empirical fields, such as male peer groups, education, sport and different national contexts where people tend to find expressions of this form of intolerance. The chapter discusses the connection that is often made between the construction of masculinity, homophobic sentiments and different strategies to regulate sexual boundaries and sustain heterosexuality. It also discusses the problematic relation between visibility—coming out as a homosexual in public—and violence. Violence against lesbian, gay, bi, transgender (LGBT) people is a central issue in discussions on homophobia. Although there are social and cultural changes towards a more liberal and open attitude towards LGBT people in many countries, risks of violence and abuse are still unreasonably high.