This paper addresses issues related to family caregiving, as one of the areas of caregiving in which problems are currently arising in Japan. Family caregiving is presently inseparable from the gender relationship between men as the breadwinners and women as the caregivers. The perspective of gender equality is therefore extremely important when discussing issues related to family caregiving. This paper focuses on the increasing number of male caregivers in Japan, and looks at the actual circumstances of caregiving by male caregivers to investigate what significance the increase in male caregivers may have for achieving gender equality in family caregiving. As men engage in caregiving, they are forced to confront their own masculinities. The difficulties that they experience demonstrate that care and masculinities are not simply conflicting aspects of their identities. In order to achieve gender equality in family care-giving, it is necessary to carefully decipher the complex interplay between care and masculinities.