This article provides a critical sociological examination of how Hong Kong youth's relationship towards Chinese identity and China is negotiated vis-a-vis schooling, language policy, and the broader Hong Kong postcolonial condition, and how this mediates these students' aspirational imaginations regarding possibilities of studying and working in mainland China. Through focus group interviews with middle-class senior secondary school students studying in English as medium of instruction (EMI) Hong Kong government schools, we highlight the conflicted relationships students had towards China, which is embedded within historical memory, but complicated by the contrasting values inherent in Hong Kong as a global financial hub and neoliberal node. Despite the school's active policies promoting Chinese cultural identity, deep ambivalences associated with Chinese sociopolitical values affected aspirational capacity. Furthermore, language policy and language acquisition are implicated in the formation of Hong Kong students' spatiotemporal aspirations towards China.