This paper examines the layered nostalgia embodied by one specific spatiotemporal site, the war‐torn Republican capital of Nanjing, in Bai Xianyong’s 1971 collection of short stories Taipei People and in Ye Zhaoyan’s 1996 novel Nanjing 1937: A Love Story. Both Nanjing’s historical reputation as an ancient capital for several short‐lived dynasties and its special role in narrating Chinese identity and cultural traditions across the 1949 divide contribute to the city’s symbolic significance in the literary tradition of ruin gazing. In the two texts under discussion, the layered ruins of Republican Nanjing—reminiscent of the decadent Six Dynasties (220–589) and witnessing the historical violence and physical as well as metaphorical dislocation resulting from World War II and the Chinese Civil War—constitute an ideal site for reflecting upon not only personal and national traumas but also traditional‐modern tensions from diversified stances and angles. The related but divergent trajectories taken by Bai’s and Ye’s nostalgic gaze—one projected from the United States in the 1960s by way of post‐1949 Taipei and the other geographically located in contemporary Nanjing but culturally distanced from it—form an interesting dialogue, which may shed light on the fluidity of ruin gazing at a nexus of identity questions with reference to the embrace of modernity.