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In this article I examine aspects of the relationship between mothers and sons from an attachment perspective in an Irish context. Through the works of Irish writers such as Seamus Heaney, John McGahern, and Colm Tóibín, I focus on particular aspects of this relationship, which fails to support the developmental processes of separation and individuation in the many men who come to me for psychotherapy. I illustrate key points concerning this attachment dynamic through the use of clinical examples of my work with two men from my practice. While acknowledging that many other cultural factors play a significant role in the emotional development of children, integrating the work of our poets, novelists, and scholars with an attachment perspective, offers an exciting lens through which to view many of the issues discussed in this article.