Taiwanese masculinity was not defined only by young intellectuals and social elites. Rather, it was constructed, expanded, and complicated by ordinary men as represented by household heads and their family members. This chapter explores their masculinity by revealing the ways in which they continued to negotiate with judges over the treatment of brides and adopted daughters. Household heads had traditionally been free to choose their sons’ brides and preside over any adoptive deals, and thus they established masculinity as tied to household authority. Yet, this unchallenged image of patriarchy began contradicting judicial calls for a more equitable form of the family from the late 1910s. What involved those household heads in judicial reforms was the situation in which two or more household heads competed over the better treatment of brides and adopted daughters, establishing a protective form of masculinity. However, this did not end with the emasculation of male household heads in terms of their preexisting authority; instead, they shifted to a type of masculinity involving collusion between two or more household heads and colonial judges, undermining efforts to address women’s difficulties after the 1920s.