Women’s agency was contingent on the multiple parties concerned with it, and they formed its gendered understandings and practices. This chapter traces those understandings and practices in the courtroom, where Taiwanese women in premarital sexual relationships expressed their interests. From the early 1920s, more women made their voices heard in civil cases on marital affairs and divorce, which revealed changing attitudes toward marriage and premarital sexual relationships among themselves, their partners and family members, and Japanese judges. The judges joined the male litigants in highlighting the formal state of marriage and wifehood against women’s informal personal status and their sexual histories. Meanwhile, Taiwanese women continued to react against the discriminatory treatment of premarital sexual relationships and eventually won the more flexible treatment of premarital relationships as if they were formal marriages in the mid-1930s. However, this result was achieved only when those women agreed to be submissive to their male partners or otherwise considered promiscuous. Changing the direction of their sexual, marital, and family lives took on a gender-specific tone.