Crying is generally understood to be an expression of emotion and is therefore, considered a useful activity within the therapeutic relationship; yet little is written about why this is so. This dissertation explores the ways in which crying has been thought about in therapeutic theory and practice. The methodology used is a modified systematic literature review with clinical illustrations. This work seeks not to look at the causes for crying per se, rather it addresses what happens between individuals when crying occurs, and how crying impacts on and is influenced by the therapeutic relationship. The literature reviewed lends itself to three main areas for investigation from a macro-to-micro view of tears. Firstly, literature provides a historical context for the notion that crying can be cathartic, which leads to an exploration of what in particular might be needed in the therapeutic relationship for catharsis to occur. Secondly, crying as attachment behaviour from infancy to adulthood is explored. This lays the basis for specifically looking at how attachment styles and crying behaviour might play out in the therapeutic relationship. Thirdly, the literature from a more inter subjective viewpoint on crying is examined and the occurrence of the therapist crying with the client is considered. Findings indicate that catharsis through crying may create intrapsychic change through the interpersonal relationship in which it occurs. Clinical implications and areas of further research are proposed.