Commonly referred to as “cougars,” women who date younger men are often imagined as sexually assertive women who actively seek out and seduce younger men, therefore challenging major pillars of the traditional heterosexual dating script. Drawing on 55 semi-structured interviews with women aged 30-60 who date younger men, I explore the relationship formation process women experienced with younger men with the intent of shedding light on women’s behavior in that context. I found that, contrary to common cultural representations of “cougars,” very few women depicted themselves as seductresses who pursued younger men, with younger men passively waiting to be courted. However, the tendency to present oneself as having played a rather passive role during the relationship formation process was more pronounced among participants over 40 than among 30-something women. I argue that in the context of age-hypogamous dating, women’s ability/desire to renegotiate the gendered script for relationship formation is constrained by the common cultural discourse indicating that a woman’s worth declines with age, as well as by the cultural discomfort toward older women’s sexuality.