This article reports on an empirical study investigating what and how two college-level American learners of Mandarin Chinese developed their own understanding of the Chinese complimenting speech act while participating in a 7-week intensive language study abroad program. A case study approach was adopted with a focus on participants’ self-reflection data supplemented with the researcher’s observation data to unpack each participant’s pragmatic developmental process throughout the program. Guided by sociocultural theory, the study uncovered the dynamic, complex and highly individualized developmental process each participant experienced. The findings revealed that Chinese people’s special treatment of the two American students provided more constraints than opportunities for them to acquire Chinese complimenting. However, the learners’ own motivation and approaches to learning also significantly shaped their learning process and outcomes. Pedagogical suggestions for Chinese pragmatic development in study abroad contexts are provided.