Academic scholarship hasn’t engaged seriously with adolescent love and romance. The only discourses within which adolescent subjectivity is spoken about are those of protection, consumption and risk. Romance among middle-class urban adolescent boys is viewed by schools, teachers and parents as either not serious – as ‘puppy love’ – or as ‘dangerous’, thus a reason for moral panic. In this chapter I critically engage with young people’s narratives about their romantic lives in an attempt to unsettle the discourse of adolescent love as puppy love and rethink gender relations. I examine adolescent male romance and consumerism, experiences and ideas of heterosexual romance, the relationship between sex and romance, and experiences of indeterminacy, failure, and uncertainty. These, I argue, question our ideas of male desire and allow me to re-conceptualize adolescent male desire.