This paper provides an in-depth analysis of a group of young rural men's and women's understandings of 'the city' and 'the country', and the relationship between this and their educational decision making. The analysis adds to a growing body of literature on young rural people's experiences and the emerging research on education in a rural context. Drawing on participant observation and interviews with a group of Grade 10 students in a rural Tasmanian high school, I argue that the everyday life of the young respondents is characterised by a high degree of ambivalence towards urban living which sits at the heart of their educational choices. They depicted living in a small rural town as involving a daily trade-off between a welcome familiarity and a problematic lack of privacy. Their perception of the city was that this relationship would be reversed, and that while they might be free from the constraint of everyone knowing your business, they would struggle to negotiate the alien environment. Using Simmel's (1950) ideas on how rural and urban environments produce different worldviews as well as Bourdieu's (1990) concept of habitus, this analysis captures this ambivalence and the sense of risk involved in exchanging the known difficulties of the town for the unknown risks of the city. This sense of the city as 'too risky' informed many of the participants' decisions to 'not make a choice' and remain in their familiar environment rather than moving to the city to continue their education and risk failure. The analysis also draws on Bourdieu's concept of cultural capital and Connell's (2005) theory of hegemonic masculinity to emphasise that although the young people shared common experiences, these were mediated by aspects of cultural knowledge and gender relations.