The function of female figures in Hermann Hesse's work has often been approached from a biographical point of view with reference to the actual mother and to women in Hesse's life. Most women in Hesse's work are seen as either saints or whores: ideal, inhuman entities not unlike statues of the Madonna, which signal their author indebtedness to German Romanticism. A different approach is attempted in this paper which takes as its point of departure the protagonist inability to have a meaningful and lasting relationship with them. This involves analysing the rhetorical and allegorical language with which women are introduced, leading to consideration of the male-female relationships in terms of British object relations psychoanalysis and attachment theory (Klein, Winnicott, Bion, Bowlby) and recent research at the Tavistock Centre. The premise here is that Hesse's male protagonist is unable to achieve a secure attachment to his mother The trauma of the unavailable mother in infancy is not broached directly in the novel; instead, her striking absence is complemented by examples of the melancholic genre where the hero often does not know what he has lost or is missing. Hesse provides extreme experiences of total consciousness and mental transcendence or total sensuality without a real connection to the woman-(m)other. A split personality is found in several of the later novels.