In this paper, I use comparisons of Freud, Loewald, and Plato to explore what it means to individuate and to desire in a world of frustration, pain, and loss. The metaphors of the “wheel” versus the “ladder” present basic images for Freud's tragic conception of a person's emerging into a world of pain, transience and loss, in contrast to Loewald's sense of individuation as an increasing attainment of individual ego and world enrichment, constructed from metabolized grieved objects. I then argue that Plato's Symposium offers comparable visions of the possibilities of love, and that the juxtaposition of Freud and Loewald can be connected to ancient philosophical considerations. The paper begins by examining the implications of the two thinkers' treatments of the “oceanic state” (primary narcissism), then compares these to the speeches of Aristophanes and Socrates/Diotima. The conclusion touches on the relevance of the juxtaposition to the Platonic distinction between philosophy and poetry.