This study explored, from a public health perspective, factors that contribute to inconsistent condom use by men in Curacao through semi-structured face-to-face interviews with 21 heterosexual men. The findings show that there is an important disconnect between what is considered culturally appropriate sexual behaviour for men and women and condom use, that diverging from prescribed notions of masculinity and femininity in order to use condoms consistently is difficult, and that condom use is particularly problematic in the context of concurrent partnerships and sexual economic exchanges. Participants further reported that Caribbean family structures, whereby mothers assume the role as primary caregiver and fathers contribute biologically but, to a much lesser extent socially, also have an impact on condom use. Additionally, consistent condom use was reported to be impeded by a cultural taboo on talking seriously about sex and sexual health. In their totality, findings provide important input from men for the development of sexual health promotion interventions that are cognizant of the cultural context in which inconsistent condom use occurs, and that are geared not only to the individual level but also to the interpersonal and structural levels.