Despite growing research on mainland Chinese international students’ intercultural language learning and adjustment experiences in Anglophone countries, few studies have delved into these students’ socially constructed language learning practices as an essential component of their study-abroad journey, especially in Singapore which shares linguistic and cultural affinities with China. As such, building on Darvin and Norton’s (2015) theory of investment at the intersection of identity, capital, and ideology, this case study focuses on Chinese foreign talent students in Singapore and aims to understand how they invest in learning English as an additional language (L2) and assert their legitimate place in the transnational context. Based on the analysis of data collected from two focused students (Baoyu and Gongcai, both pseudonyms), this study reveals the varied, complex, and agentive ways in which the two cases invested in English learning and English-mediated social interactions. It showed that both participants developed different investment pathways, which were shaped by their endeavors to reconstruct desired identities and their motivation to actualize capital conversion. Their investment in English language learning was also largely impacted by dominant ideologies and institutional policies. This study contributes to the field by highlighting the role of social networks in shaping learners’ investment practices, the influence of cultural capital on their investment choices, and the role of agency in challenging prevailing ideologies and navigating sociocultural dynamics in the study-abroad context. This study also proposes educational and policy implications concerning Chinese foreign talent students in Singapore and points out directions for future research.