This paper presents results on the intergenerational transmission of interpersonal problems. Ninety-eight German mothers, fathers, and their young adult offspring completed the German version of the Inventory of Interpersonal Problems (IIP-D64), which is conceptually based on the assumption of a circumplex structure of eight interpersonal problems. Model learning and psychodynamic theories were used to formulate assumptions about possible intergenerational similarity and dissimilarity, as well as about effects of family and societal context. The results showed the highest intergenerational correlations for three of the eight interpersonal problems in the IIP-D64, namely nonassertiveness, overly strong accommodation, and self-sacrificing tendencies. Intergenerational similarity was found only for mother–offspring dyads for two other problems: domineering and vindictiveness tendencies. No significant intergenerational similarity was found for coldness, social inhibition, or intrusiveness. In-depth analyses revealed higher similarities in families in which at least one parent had an overall IIP-64 score equal to or more than one standard deviation from the norm sample mean (as opposed to families where both parents had overall IIP-64 scores closer to the normative German mean). The findings are tentatively interpreted as suggesting that intergenerational transmission occurs only for problems on one axis of the interpersonal circumplex, i.e., the agency axis, but not for problems on the communality axis.