The tradition of Western painting is organized in part by the unspoken assumption that men actively look and women are objects to be looked at. Unsettling Femininity probes the politics of viewing and questions the ways we habitually look at images of women, through the particular lens of the Frye Art Museum’s collection and the aesthetic preferences of the Museum’s founders, Charles and Emma Frye. The exhibition examines historical conventions of representation and the deeply entrenched beliefs and power structures they reflect—especially concerning gendered expectations around appearance and behavior. The exhibition focuses primarily on portrayals of white women by German artists from the late 19th and early 20th centuries. The depicted women assume specific postures, gestures, and expressions that highlight the performative nature of gender as specific sets of socially learned and patterned behaviors. Many of the works emphasize traits such as submissiveness, vulnerability, and sexual availability that corresponded to pervasive 19th-century cultural attitudes about what constitutes an ideal feminine nature and body. Others deliberately challenged more conservative Christian sensibilities prevalent in cities like Munich by creating confrontational images that eroticized female religious figures. Whether these images associated women with virtue and beauty or danger and sex, they re-inscribed moral boundaries that ultimately upheld the patriarchal status quo. Many of these female figures strike the contemporary viewer as “unsettling,” their postures or facial expressions seeming to demand a narrative explanation that the painting does not supply. From pairing portraits in ways that highlight the artifice of painting or contrasting constructed ideals of natural femininity against portrayals of seductive performers, the exhibition asks viewers to reconsider the very act of looking, in all of its positive and negative connotations.