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In order to grasp the complexity of the events in Hong Kong leading up to the imposition of the National Security Law in 2020, a feminist critique inspired by Lauren Berlant’s notion of “cruel optimism” provides a productive place to expand the conversations about the role gender plays in the territory’s political culture. Concentrating on the period between October 1 and December 31, 2019, this analysis examines this more violent but also more optimistic period encompassing the lead up to the District Council elections and subsequent events before COVID-19 upended the city in early 2020. A feminist lens magnifies the discourses circulating through mass and social media. Attention turns to forms of political expression in films, cartoons, literature, and the other arts, which highlight the ways in which gender and sexuality play their parts in the cruel optimism of Hong Kong’s protest culture.