This article concerns the complex negotiation of ageing and femininity in Amy Heckerling’s two most recent films: I Could Never Be Your Woman (2007) and Vamps (2012). These films are positioned as part of the contemporary postfeminist media culture, (Gill, 2007) noting the scrutiny received by the ageing female body, and its changing status under the prevailing cultural norms of femininity. However, Heckerling’s films also demonstrate a sense of play with these gender norms, and so calls to be read also in terms of Judith Butler’s theorisation of performativity (1990; 1993; 2004). This article contends that Heckerling’s representation of liminality and indeterminacy—in her teen movies, and later work alike—provides a way for women to carve out an autonomous identity that humorously demonstrates the absurdity of mediatised constructions of femininity. Her work, then, is more complex than has hitherto been acknowledged, and the piece concludes by calling for the director and screenwriter to be repositioned as a significant female voice in 21st century screen media.