By examining the descriptions of old things in medieval Chinese writings, this paper finds the appearance of a culture of sentimentality at the turn of the 9th century. This culture of sentimentality indicates a deep-seated anxiety about the blurred boundary, on a conceptual and ideological level, between humans and things, and bespeaks the complex dynamics in the relationship of self and other at a time of profound cultural and intellectual changes. It anticipates and yet remains profoundly different from the Northern Song antiquarianism, thus revealing gaps and fissures in the neat teleological narrative of the “Tang-Song transition.”