The study aims to provide a philosophical and cultural analysis of the problem of the ambivalence of female images in Eugene Vodolazkin's works by means of the concept of time-spiral as developed by the writer (this concept has been proposed and substantiated in his programme novel Laurus). The relevance of referring to this topic comes from the opportunities that such an examination provides for understanding the dynamics of the value bases of contemporary Russian culture. The research materials include E. G. Vodolazkin's fiction prose (novels) and his interviews (in particular, the interview with the writer conducted by one of the authors of the article — O. S. Korkina). The study uses a comprehensive culturological approach combining phenomenological, hermeneutic, and biographical methods. It is concluded and proved that the ambivalence of female images manifests itself at different levels of Vodolazkin's works. This ambivalence is observed by an open opposition of several female types through the prism of their evaluation by the narrator. Women in Vodolazkin’s prose bring the protagonist closer to Eternity, some of them stand by him, tempt him, or leave him. There are those who can give life and those who cannot. The axiological vector of Vodolazkin's prose consists of the opposition between traditional and modern values, embodying active and passive female characters. Meanwhile, the actual reading of the medieval passive type contrasts with the antagonistic image — a contemporary, psychologically and narratively active woman, whose personality has been influenced by feministic ideas and whose character, in a complex way, resonates with the traditional reading of femininity, as if building on it. Thus, the female images exemplify the paradoxical unity of a multifaceted human nature and show how its cultural existence unfolds cyclically in time through the acceptance and repulsion of Vodolazkin's basic values.