Self-alienation is curiously both a condition that is pervasive as a felt phenomenon but also seemingly paradoxical. As a relation to the self, how can we be distant from ourselves? From what standpoint can we occupy such that we can be alienated from ourselves? That standpoint would just be the self that we inhabit. Another aspect of this paradox is that for some moral theories it would be seemingly impossible for an agent to intentionally undermine themselves. Self-alienation puts the agent in a position where they are not only distant from themselves, but also hostile to themselves. Despite this paradox, self-alienation is a common feature of both literature and various philosophical treatments on alienation. This dissertation is an exploration of how self-alienation can be possible. There are two main arguments I am going to make: (1) that most traditional explanations of self-alienation try to get around the paradox via an “othering” process whereby a part of the self is transformed into an “other.” I argue that this is a kind of “weak” self-alienation where the agent is not really alienated from herself but alienated from a part of herself she no longer identifies with (and in consequences, she does not see that as part of herself). (2) That a stronger form of self-alienation involves two wholehearted practical identities mutually undermining each other. These identities have to be tied to the essential features of a rational agent, and in their undermining of each other, create a kind of absurdity that the agent cannot reconcile. Finally, I will consider both how this strong form of self-alienation is possible under formalist contexts, and what some possible resolutions are to this kind of alienation.