Eliciting user requirements from HIV-positive gay men who smoke can be challenging. This is because of the complex relationship between social stigma and gender identities (e.g., gay, masculine, HIV+, and smoking status). Inspired to engage HIV-positive gay men in the development of a web-assisted tobacco intervention, we used personas as a main communication tool in our participatory design sessions. Personas are characters created by users that embody part of their own behaviours, thoughts, and motivations. In an apparent paradox, this article is a description of how the use of personas to ensure less realistic self-representation provided an impetus for more self-disclosure. Findings and feedbacks from this study reveal that personas are an effective design tool to engage users in sensitive topics. Implications for future work are also discussed.