This paper is a theoretical study exploring Winnicott’s concept of ‘holding’ and Bowlby’s concept of ‘secure base’ and their implications for the therapeutic relationship. Particular attention is given to the parallel maternal metaphor in both providing a ‘holding’ environment and a ‘secure base’ in the role of a therapist. This paper further explores how Attachment Theory echoes and expands upon Winnicott’s work with a particular focus on John Bowlby’s work. Bowlby posits that the secure base provided by the mother in infancy mirrors the manner in which a therapist provides a secure base for clients to facilitate internal exploration. The secure base mirrors Winnicott’s concept of ‘holding’ which also facilitates exploration and ultimately, the move ‘towards independence’, both in early relationships and the therapeutic dyad. This paper includes an exploration of the research on these concepts and concludes with an examination of the convergences and divergences between Winnicott and Bowlby as theorists, both personally and professionally, and a critical examination of the implications for the use of both theories in practice. It is hoped that examining the parallel maternal metaphor within these theoretical frameworks will further illuminate the inner workings of the therapeutic relationship and ultimately, the primacy of human connection and relationship.