The paper examines what Nancy Chodorow (2012) calls the ‘paranoid-schizoid fantasy’ in relation to gender which, I suggest, lies in the deep unconscious of both men and women as they attempt to translate anatomical and biological differences into a social and relational mind. The paper concentrates on masculinity and examines the deep anxieties in the male regarding the feminine identification. It argues that the feminine identification in the male makes the innate bisexuality in males a lived reality but, as Freud has demonstrated, bisexuality is full of conflicts and pitfalls and very rarely are human beings at home in their own gendered self. The ‘dread of woman’(Freud 1918, ) is first and foremost the dread of the feminine within the male self which is often experienced as undermining the male identity. Freud’s ‘dialectical’ thinking about masculinity and Klein’s ‘femininity phase’ are examined to look at the deep, infantile, repudiated male wish for femininity and passivity.