This chapter examines the theoretical and discursive construction of homoeroticism and its alignment to both homosexual and heterosexual masculinities. It critically locates the discourse of the homoerotic through cultural norms, hegemonic power relations and, perhaps most potently, how desire between men is articulated. It details homoeroticism’s relationship to romance, effeminacy and narcissism and how this can be allied to homosocial contexts and settings. The chapter further unpacks more detailed terms and concepts connected to new ways of articulating and performing masculinity which in turn inform new ways of conceptualising and thinking about homoeroticism and masculinity.