Beyond the inevitability of countertransference feelings is the question of countertransference enactments. From a two-person, participant-observer or observing-participant perspective, enactments are inevitable. The analyst becomes influenced by the patient (and influences the patient as well) and enmeshed in the patient's internalized interpersonal configurations. Analysis works not by avoiding such action but by analyzing from within the interactional system. Analysts who are different from one another become engaged in different ways, since the person of the analyst is a significant variable. This article, using case examples, explores two analyst-related variables, age and family configuration, to expand the examination of countertransference enactments and some effects on the analytic process.