Caring is typically constructed as a feminised practice, resulting in women shouldering the burden of care-related work. Health-seeking behaviours are also constructed as feminine and men have poorer health outcomes globally. Employing men as carers may not only improve the health of the men they assist but also be transformative with regards to gendered constructions of caring. Using semi-structured interviews and observational home visits, this study explored the techniques that community care workers employ when working with male clients. The empirical analysis draws on the perspectives of eight care workers and three of their male clients from the Cape Town area. Interviews reveal how care workers and clients perform and negotiate masculinities as they navigate hegemonic masculine norms that require men to act tough, suppress emotions and deny weakness and sickness. Both parties bump up against ideals of what it means to be a man as they strive to provide care and receive support. Community care workers avoid rupturing client performances of hegemonic masculinities which inhibit confession and support. To do this, they use techniques of indirectly broaching sensitive subjects, acting in a friendly way and being clear about the intention of their work.