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This article reads Hollinghurst’s The Folding Star through a synthesis of Freud’s theories of transference and the death drive and Jean Laplanche’s theory of infantile masochism. My reading traces the role of masochism in the formation of the gay male subject and in this way contributes towards an understanding of the repressed masochism which is central to psychic life, and more specifically to an understanding of its role within masculinity and gay masculinities. Through this reading I attempt to shed light on the problems of such an identity both for the subject and for a relationality at work within Hollinghurst’s novel which is consistently dependent upon a melancholic preservation of heterosexual masculinity.