Adolescence is a dynamic period of transition, and interaction with parents is important for successfully passing through it. This article presents results from a study of three transactional analysis theory personality constructs of adolescents and their parents—functional ego states, life positions, and stroke economy. The sample included 215 students from 12 to 16 years old and 215 parents from 30 to 55 years old. The results show significant differences between the ego states Adult, Adapted Child, Nurturing Parent and Normative Parent of the adolescents and their parents, which are more expressed in the parents. It was found that the life position, “I am OK—you are OK” is more strongly expressed in parents, while the life position, “I am not OK—you are not OK” is leading in adolescents. In their interactions with others, adolescents express modesty, self-doubt, and underestimation of their own success, while parents are more assertive, confident, and resilient in their behavior. The obtained results can be used in different programs to improve social interaction and increase the effectiveness of adolescent-parent relationships.