The detailed interview is a classic method of qualitative data collection. To be conducted effectively, interviews demand considerable skill and judgment. Nowhere is this more critical than when working with participants from disadvantaged and marginalized populations and when the research examines stigmatized conditions and taboo issues. To explore the techniques involved in researching these issues, this case study unpacks the approach taken for the Caribbean Masculinities Project. The Caribbean Masculinities Project used in-depth interviewing to explore ‘coming of age’ and ‘becoming a man’ among 138 diverse young Caribbean men from eight countries. The practical experiences and the lessons learned are outlined. While the techniques described here can be applied in any interview-based research, they are especially important when working with taboo issues (such as sexuality and gender non-conformity), stigmatized conditions (such as HIV) and marginalized populations (such as young gay black men growing up in homophobic settings).