The aim of the article is to discuss, from the psychodynamic point of view, some of the problems that appear during individual and out-patient-facility-located therapies of adolescents with varied symptoms that give rise to the anticipation that their development may be directed towards pathological personality formation. The symptoms are often dangerous for their health or life (suicidal thoughts and attempts, self-injuries, eating disorders), or create severe conflict with their natural environment (social isolation, abandoned education, antisocial tendencies, etc.). Based on the presented cases, diagnostic issues are discussed, for example: to what extent does the diagnosis of personality disorder make sense in the developmental age? What arguments can be used for and against the use of this category in a developmental age? To what extent is an adolescent's personality type determined in the period of adolescence? How can one understand and diagnose the presence of often dramatic symptoms in adolescents using psychodynamic categories? The aim of the author is to indicate the usefulness of describing difficulties appearing in the adolescence period, in the developmental categories. Another area that is discussed describes difficulties appearing during the therapeutic process. The examples of such difficulties involve: connecting and maintaining a relation, lack of motivation for therapy, counter-transference phenomenon, and dangers presented by teenagers' destructive acting out to themselves.