This study entails a qualitative cultural film analysis of single women characters in six contemporary US-American movies released between 1999 and 2008. On the one hand, the focal point is the assessment of character portrayals and their embedding into their everyday lives. On the other, it focuses on the correlation between age, gender, and marital status. Results show that an acknowledgement of different kinds of single older women seems prevalent, yet also reveal a dominance of hetero-normativity. It is concluded that Hollywood offers a so called counter world of single women and aging, particularly with regard to socio-economic strains, health, and an active aging process where one can look ‘younger’.