This thesis is an exploration of the shame that inheres in not being able to self-admire. I call this incapacity to admire oneself ontological shame, and I argue that it is the source of the masquerades, concealments and negative emotions that surround the pursuit and defence of a self-esteem founded on an impoverished form of pride. I argue that there is a radical asymmetry between our admiration and esteem for others and how we evaluate our own sense of self-worth. Where admiration at its highest pitch is the wonderful agape experience of apprehending preciousness in others, our own sense of self-worth is limited to experiences of pride and other forms of self-affirmation; none of which allow us the joy of seeing ourselves as wonders in the world. Because we can admire and want to be admired, not being able to self-admire amounts to a limitation of a sort which carries with it a primordial resentment against life itself. It is largely how we respond to our ontological limitation and to our resentment that determines the positive or negative manner in which we interact with others, and whether or not we are likely to have an envious or humble disposition. In the first three chapters I lay the groundwork for the main argument of the thesis by highlighting the difficulties self-esteem theorists have in agreeing upon the value of ‘high’ self-esteem, introduce the relation between self-esteem and shame, argue for a distinction between self-esteem and public esteem, and provide an account of the gift-exchange nature of admiration which explains why we cannot self-admire. In the central chapters I focus on shame; on acts of concealment that can be either appropriate covering for, or deceitful denial of our ontological limitation; how self-worth is created through a reconciliation to shame, and why the ‘self-act dissociation’ theories of guilt fail to capture the shame attached to ‘being guilty’ of a wrongdoing. In Chapters Seven and Eight I examine envy, first in how it can be disguised as moral resentment; how it differs to admiration in its role in emulation, and finally how as a disposition it stands in stark contrast to humility. It is in humility that we grasp the benefits associated with our own incapacity to self-admire through our need to interact and exchange gifts with others.