This study examines characteristics of stay-at-home father (SAHF) families in Hong Kong and factors contributing to their increase. Based on two decades of census data (1991–2011), we find father's older (relative) age, lower education relative to their spouse, and lower household income increase the probability of having SAHF arrangements, leading us to believe that some fathers enter SAHF arrangements because of their inability to work or due to unemployment. Younger age of children, which often implies more intensive work, lowers the probability of unable-to-work SAHF arrangement, while increases the probability of caregiving SAHF arrangement. While childcare gap between caregiving SAHFs and stay-at-home mothers has narrowed, the effect of the number of young children on caregiving SAHF households has become negative over time. These results imply the conflicting forces SAHF families face: notions of masculinity that exclude childcare are at odds with the increasing value of paternal participation in the lives of young children.