This paper will critically explore elements of the psychoanalytic paradigm of developmental psychology in relation to the professional practice of working with teenage mothers in an educational setting. Particular focus will be given to the psychosexual and psychosocial staged theories of development. The framework for this critical analysis will examine each stage of psychosexual and psychosocial theory in relation to teenage motherhood. These perspectives have been specifically chosen due to the explicit links between staged childhood experience and adult behaviour in relation to sexual and social aspects of development, both aspects having fundamental links to teenage parenthood. Four case study examples are used to demonstrate how psychoanalytical theory may relate to this cohort. These are taken from my past professional work as a teenage parent programme lead. The examples are given to shed light on the impact of each psychosocial and psychosexual stage of development. This article concludes that whilst both the psychosocial and psychosexual models of development are useful in giving educators a perspective into behaviours that are displayed in adolescence, they are but one of many perspectives that should be taken into account when working with this cohort.