A wealth of studies has shed light on how the identity and emotions of English as a Second Language (ESL) teachers are formed and interinfluenced. However, very few studies focus on a specific emotion of ESL teachers that adversely affects teacher professionalism. Drawing upon the notion of melancholy (Brady and Haapala 2003), this chapter conducts narrative inquiry and thematic analysis to investigate how melancholy is experienced by early career English teachers in their narratives. The research is conducted through a longitudinal qualitative multiple-case study of three ESL teachers working in secondary schools for seven years in Hong Kong. Specifically, the chapter elucidates how socio-cultural factors, such as self and personality, school culture, peer relationships, and student performance, contribute to the melancholy experienced by ESL teachers. The findings of this study serve to conceptualize the melancholic sense of ESL teachers regardless of institutional changes and provide implications for enhancing the well-being and career sustainability of ESL teachers in Hong Kong. Copyright © 2024 The Author(s), under exclusive license to Springer Nature Singapore Pte Ltd.