Gay men living with HIV (GMLWH) who smoke are less responsive to generalized smoking reduction and cessation (SRC) programs than heterosexual persons. This study explored perspectives of GMLWH during the design of a web-based SRC intervention. Participatory design techniques were used to guide the creation of personas that are composite representations of a person who would use the web-based SRC intervention. Researcher-participants (n = 13) created all data. Data analysis involved thematic coding drawing from an ethnographic perspective. Thematic analysis revealed seven intersecting themes related to SRC among participants, and an overarching theme navigating life. Concepts drawn from our ethnographic approach highlight cultural differences between GMLWH and mainstream society. Personas offer a mechanism for interpreting experiences and traditions of GMLWH. SRC interventions with GMLWH must address their social realities that include tools for navigating life, disease, and social identity.