The occupational choice of young people still varies sharply by gender. Following the rise in demand for qualified workers in the care sector, the educational policy goal of “cliché-free occupational choice” and the idea of attracting more men are frequently put forward as a possible solution. But what motivates men to embark upon training in care occupations, where women make up the majority of new entrants? And what significance do they attach to gender-related perceptions of a person’s characteristics? This article uses interviews with trainees in three different care occupations to highlight the occupational perspectives being pursued and to discover how they come to terms with aspects of gender and masculinity. Is it possible that they are constructing new concepts of masculinity?