In this chapter, I propose to examine a specific form of self-awareness in which we become aware of our existence in a problematic sense: wistfulness. In thinking about what it means to have a life, one is often haunted by different senses of possibility: of what could or should be, of what might have been, but just as well, of what could never have been. In such latter instances, we become aware of ourselves not in terms of actuality (who I am) or possibility (who I can or could become), but in terms of impossibility, namely, as the impossible selves that nonetheless, in some sense, define and hence belong to us, as attested to in the experience of regret and remorse, not for what we did (or who we have been) but for what was impossible for us to be (or do). Drawing on Georg Simmel’s philosophy of life, I shall explore various senses in which we are responsible for ourselves, of who we have been and could yet be, as well as who it was impossible for us to once have been. In this regard, what Simmel calls the meta-ethical significance of death refers to the responsibility we have for ourselves in terms of what was both possible and impossible for us.