Persons exhibiting narcissistic personality traits are difficult to treat in psychotherapy, in particular because of the problems they have in building up a sound therapeutic relationship. We discuss the hypothesis that the threats to a therapeutic alliance emerge both from patients' maladaptive patterns of behaving towards others and from therapists being affected by these patterns and becoming a part of a dysfunctional dialogue. We examine this phenomenon in terms of Dialogical Self Theory and suggest that a patient can be conceptualised as embodying a cast of characters weaving a problematic dialogue both within the self and with other selves. Via the analysis of the transcripts of the first four audiotaped sessions of a psychotherapy involving a woman with narcissistic traits we identified one early dominant dialogical pattern in which a contemptuous and a contemptible character faced each other, shadowing characters in search for help. Such a pattern is consistent with the literature on interpersonal processes in narcissism. The therapist was involved in the pattern from the third session, suggesting that countertransference with individuals displaying narcissistic personality traits is caused more by the pathology than by their therapist's characteristics. Implications for treatment are discussed.