Based on Self-Determination Theory, our study examined the associations of maternal perspective taking (PT), clear expectations (CE), and their interaction during mother–male adolescent conflict with sons’ externalizing and internalizing problems. Fifty-one mothers and their 16.5 year old sons were observed while conducting a revealed differences task. Maternal PT and CE during the interaction were assessed using new scales derived from the individuality and connectedness Q-sort. Sons’ externalizing and internalizing problems were measured using the Youth Self Report. We found that higher maternal PT was associated with fewer externalizing problems of sons only when mothers also showed high levels of CE. Thus, in situations involving parent–adolescent conflict, parents’ sensitivity to adolescent opposing perspective coupled with clear statements regarding the expected adolescent behavior may relate to better socio-emotional functioning of male adolescents.