Drawing upon Professor Higgins in George Bernard Shaw's Pygmalion as a template, and making use of clinical material, I will reflect upon the painful, poignant and self-inflicted inner loneliness of the narcissistic individual. In order to master early trauma, the narcissistic person constructs an outwardly substantial self in which he seeks to control others and the way he is perceived by others. In so doing he renounces the more emotionally vulnerable parts of himself, the very parts he needs in order to develop a more authentic self and emotionally connect with others. Sometimes a crack appears in his defensive narcissistic structure with the possibility of something more life-enhancing emerging.