This article focuses on the early Republican theater as a popular site of experiments with love and discusses the significance of pengjue courtship between actresses and male patrons. It argues that while the literati still played a role in shaping theater patronage culture, employing the discourse of qing and the scholar-beauty romance, the popularization of pengjue enabled a more flirtatious mode of love that combined male homosociability and heterosexual desire. Male patrons’ courtship of actresses was marked by frivolity and performativity, as well as economic calculations. It deviated from the traditional ideal of qing and the New Culture notion of romantic love and thus aroused intense criticism from conservatives and reformists alike. However, this article argues that the practice of pengjue created an alternative affective sphere for performing gender, contesting social norms, and exploring new forms of love in the public space of commercial theater and in everyday life.