In the postmodern era, sadness is represented, circulated, and transformed from a personal experience into digital attention. This study examines emotional representation and gender negotiation in Indonesian popular songs, the circulation of sad songs on Instagram, and the conversion of users’ emotional expressions into digital engagement. It uses netnography and gender-informed descriptive and thematic analyses of the valence scores of ten Indonesian popular songs, engagement with a post featuring “Hilang Tanpa Bilang”, and 21 purposively selected comments. The analysis examines language, subject positions, and gender norms without inferring users’ gender. Findings show that: (1) eight of the ten songs are categorised as sad or very sad, representing loss, waiting, caregiving, and life pressures that reproduce and negotiate femininity and masculinity; (2) over 1,000 posts featuring “Hilang Tanpa Bilang” demonstrate the circulation of an emotional narrative performed by a female singer; (3) 12 of the 21 comments are negative, expressing vulnerability, loyalty, self-blame, and emotional responsibility, while positive comments demonstrate agency and personal boundaries; and (4) comments constitute digital affective labour that transforms private sadness into public expression, engagement data, and visibility. The commodification of sadness on Instagram emerges through gender representation, music circulation, and digital affective labour. Instagram is ambivalent: it supports emotional recognition and solidarity while transforming gendered emotions into attention and engagement with potential promotional and economic value. By integrating valence analysis, gender perspectives, and digital affective labour, this study illuminates the commodification of sadness in Indonesia’s digital culture. .