Listening has always been a challenging skill for students, especially for those who are expected to reach the advanced level. The current study focuses on the impacts of reflective journals, in which third-year students in a tertiary school extensively conduct their listening practice out of the classroom setting, on boosting listening skills. To be more specific, it aims to investigate how students taking the “Listening 5” course responded to writing weekly reflective journals, what benefits they might offer students, and what potential obstacles students faced during a semester. Data were qualitatively collected and thematically analyzed to have an insight into the aforementioned questions. Several pedagogical implications are suggested from the findings of this study.