Geographic accounts of caving have critiqued the propensity of affects and practices which reinforce EuroAmerican coloniality and hubris, while also finding alternative paths of intimacy and lively relationality. Yet subsurface geographies can also reinforce cliched spatial and moral topographies. This article reflects on the production of an ambivalent affect of “dark humor” in caves, through caver social worlds, and in cave writing and song. I use a Bachelardian phenomenology of the imagination as a method of interpreting the geopoetics of cave space and cave emotion related topologically rather than topographically into easy interior/exterior or surface/depth oppositions. Through Jan and Herb Conn's cave ballads and poetry, imaginative place names, and accounts of irritating struggles with manganese, a different emotional culture of caving is produced than the masculine risk-seeking one might expect. Nonetheless, such phenomenological focus on immediacy of creative imagination risks precluding broader historical-political contexts of settler coloniality. Seeking a position between “ruthlessly critical” or “post-critically evasive” analyses, I consider how the Conns produced an “anti-heroic” attitude useful beyond caving and the politics of the subsurface but without purity or innocence.