Based on 25 interviews with educated and employed never-married men in Japan, this article examines how the diminished social norm to marry by a certain age, never-married men’s beliefs regarding gender in marriage, and the value these men place on individual autonomy all contribute to a trend in late marriage. We argue that the diminished social pressure to marry and the changing age norm do further men’s ambivalence toward marriage by allowing them to rationalize their detachment from the idea of their future marriage, their aversion to the perceived gender constraints of marriage, and the emphasis they place on their autonomy. However, we also argue that the weakening of the social pressure to marry does not relate to changes in employed men’s gendered views of marriage, which remain traditional.