Ideas of gender, sexuality, and subjectivity were in flux throughout the eighteenth century. This chapter places Goldsmith’s comedies She Stoops to Conquer and The Good Natur’d Man at the heart of contemporary gender debates. The theatre was a significant site for the negotiation of gender where women’s sensitivity, modesty, and gentility were touted as positive social forces capable of reforming men and improving manners by conditioning women to please others. Goldsmith’s plays can be seen as part of the ‘feminization debate’ – British discourse which trumpeted the progressive effects of women on modern society while seeking to condemn perceived transgressions of an increasingly binary gender order.