In this article, I employ a psychodynamic lens to describe how women's fantasies of time as standing still, which is encouraged by sociocultural forces, is used to undermine the notion of the biological clock. These fantasies, also fueled by the timeless nature of the unconscious, can lead to hesitancy in not only initiating fertility treatment but also in complying with fertility treatment recommendations. When this happens, hesitancy is often unconsciously utilized in a conflict about becoming a mother. Once these hesitancies are worked through in therapy through a focus on previous losses, fertility treatment often moves forward. I present the psychotherapy treatment of a 45-year-old woman with both fertility treatment hesitancy and fertility compliance hesitancy, who had not only significant childhood losses but also significant losses in her ongoing fertility treatment. I also comment how my countertransference, which urged me to work through issues quickly in therapy, was informed partly by my experience as a former obstetrician and gynecologist and hindered my work with this patient.