Through an exploration of the notion of “the gaze” and its relation to psychopathological experience, this chapter investigates from a phenomenological perspective the connection between the sense of possibility (Ratcliffe 2012a; 2015), affectivity, and narrative self-understanding. Drawing on the work of Jean-Paul Sartre, I start by suggesting that the concept of the gaze can provide a powerful metaphor for the characterisation of the alterations of experience which mark certain forms of psychiatric illness, and I argue that this is exemplified in particular by disruptions of the sufferers’ sense of what it is possible for one to experience and achieve. Having highlighted how disruptions of one’s sense of possibility have been associated with transformations of background affects, and, more specifically, existential feelings (Ratcliffe 2008; 2015), I move to investigate how these can be modulated through the engagement with certain forms of narrative self-understanding. To do so, I establish a parallel between the way in which we relate to ourselves as the protagonists of our self-narratives and how we respond emotionally to fictional characters, highlighting some of the dynamics through which we can come to experience affects which are narrated. This enables me to provide an account of how certain self-narratives can trigger emotions which are in contrast with one’s existential feelings, engendering changes which can lead to an expansion of one’s possibility space.