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Countertransference may reflect the patients' diagnosis and can be used to better understand patients' inner worlds and core conflictual relationship themes (CCRTs). Thus, the changing emotions of therapists can serve as a marker of treatment processes. This exploratory study aims to identify how the interaction between patients' CCRT patterns and their respective therapists' emotions associate with working alliance postsession and patient symptoms. The data analysis is based on 17 subjects who received supportive-expressive therapy. Therapists' emotional reactions were assessed using the Feeling Word Checklist. The Working Alliance Inventory—Short Revised and the Outcome Questionnaire were completed at each session. The relationship between the patients' CCRTs and (a) the therapists' emotional profile, (b) therapists' rated working alliance, and (c) patient symptoms was analyzed using mixed models. Results show that patients' CCRT moderated the correlation between therapists' feeling engaged and time. In addition, patients' CCRTs and therapists' emotions together was associated with therapists' rated working alliance and patient symptoms.