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The main aim of this study was to examine the relationship between patients’ self-reported personality characteristics, treatment outcome and therapists’ countertransference reactions. Eleven therapists filled in the Feeling Word Checklist 58 (FWC-58) for each patient admitted to a day treatment program. The patients completed the Circumplex of Interpersonal Problems (CIP) at admission and discharge. Outcome measures were assessed at the end of treatment. At the start of treatment, therapists reported fewer feelings of rejection and being on guard in response to patients who reported high avoidant, exploitable, overly nurturing and intrusive CIP subscale traits. At the end of the treatment, the CIP subscales of being domineering, vindictive and cold correlated with fewer positive and more negative countertransference feelings. The study revealed a strong relationship between improvement and countertransference feelings. This study confirms clinical narratives on relationships between the therapists’ countertransference reactions and patients’ reported interpersonal problems and outcome.