The rise of malaise, cynicism and disenfranchisement amongst youth has been a widely debated discourse in recent times, especially within the Hong Kong context given recent student protests. In understanding how this collective expression of protest has arisen, this doctoral thesis examines the lives of Hong Kong secondary students, and how their lived experiences influence their perceptions and dispositions of their futures, and their relations to further education and employment. Specifically, the research explores students’ understandings of their schooling experiences in English Medium of Instruction schools in Hong Kong and the broader relational impacts of globalisation, neoliberalism, nationalistic and local identities, middle class familial upbringing, and the nature of English in Hong Kong. The research draws upon Pierre Bourdieu’s theory of practice, together with Arjun Appadurai’s notions of the ‘capacity to aspire’, and Charles Taylor’s concept of ‘social imaginary’, to help make sense of students’ mediations and aspirations for the future. Bourdieu’s relational thinking and his epistemological reflexivity, coupled with the identification of Taylor’s ‘modern social imaginary’ as expressed in the Hong Kong context, and Appadurai’s notion of cultural capacity, informed the methodological approach. The collection of data involved observations and interviews with members of six focus groups across three distinctively situated schools in Hong Kong, together with compilation of publicly available documents produced by these schools. Incorporation of autoethnographic experiences helped to further contextualise the analysis. Analytically, the research shows how aspirational dispositions and logics formed by specific configurations of the broader cultural and social milieu of Hong Kong, middle class familial practices, non-elite EMI schooling experiences, and the place of English in Hong Kong, were complicit - in complex and nuanced ways – in fostering disjunctive dynamics, engendering a sense of ambivalence towards the future for these students. The research is significant because it reveals how aspirational ambivalence has become a dominant logic amongst these students, and arguably contributes to a sense of malaise and collective disillusionment amongst many of Hong Kong’s youth.