The authors present a research based on metaphor analysis applied as a means of unveiling human experience encoded in various aspects of language use. More precisely the study explores the feminine imagery as represented in American pop songs by leading female pop singers proposing a hypothesis that, within a single culture, the socio-cultural perspectives of a particular social group may alter significantly within a relatively short period of time. After the presentation of a consistent theoretical background, the qualitative contrastive analysis of conceptual metaphors is set within the framework of Conceptual Metaphor Theory, and by means of the Metaphor Identification Procedure developed by Pragglejaz Group and P.A.N., a poetry analysis software. Findings based on the examination of 522 conceptual metaphors reported in two periods of time (80s-90s and 2000-2015), related to ‘love’, ‘life’, and ‘time’, interestingly demonstrate that, while in both periods the female image is represented as a strong, persistent and self-dependent, the earlier period is characterized by more positive views on love while in latest times women are depicted as competitive and concrete, but flexible and able to adapt to a leading role in relationships. Data also support the idea that most recently women have acquired a more pragmatic attitude in considering love relationships, time and daily life in general.