Amy Heckerling's two most recent films as writer/director, I Could Never Be Your Woman (2007) and Vamps (2013), constitute a slight departure from her family and teen comedies. The first follows the conventions of the romantic comedy genre with elements of fantasy, and the second is a hybrid narrative, mixing the basic structure of the female friendship film with elements of horror. In this essay, I will examine the ways Heckerling negotiates issues of female aging and sisterhood in these two texts, using textual analysis as well as analysis of specific cinematic codes—mise-en-scène, editing, and cinematography—to reveal Heckerling's preferences and style, while utilizing gender theory to assist in the contextualization of the narratives. I will be basing my arguments mainly on Samantha Holland's Alternative Femininities (2004), and Rosalind Gill and Christina Scharff's collection New Femininities: Postfeminism, Neoliberalism and Subjectivity (2011), because I find the use of the term “femininities” that the books’ authors use inclusive and appropriate in contemporary discussions on gender. Instead of femininity being treated as a monolithic and absolute concept, its plural avoids “notions of essentialism,” and “ideas that femininity equates with young, white, slim, heterosexual, ablebodied women.” I would add that the plural also assists in the exploration of various fictional feminine performances created by the same agent, in the case of this study a single filmmaker. Heckerling's heroines may share common traits, yet they also contradict themselves and differ in interesting ways, more often than not in the same narrative, performing various aspects of femininities. Second, Gill and Scharff draw useful connections between postfeminism and neoliberalism, stressing that “the autonomous, calculating, self-regulating subject of neoliberalism bears a strong resemblance to the active, freely choosing, self-reinventing subject of postfeminism.” Because the representations I will be discussing were produced and consumed in the same sociopolitical context, it will be useful to examine the interconnections, if any, among the subtle yet pervasive influences of neoliberal principles on female agency. Indeed, as Gill and Scharff argue, “to a much greater extent than men, women are required to work on and transform the self, to regulate every aspect of their conduct, and to present all their actions as freely chosen.”