This paper examines and analyzes the records of two Lis: Li Zhongjue 李鍾玨 from Shanghai who visited Singapore in 1887, and Li Qinghui 李清輝, a Singaporean who visited Shanghai in 1888. Both Lis seemed to be quite impressed by the cities they visited and had left their impressions, observations and reflections in print. Li Zhongjue's Xinjiapo fengtu ji 新加坡風土記 (A Description of Singapore in 1887) is a widely circulated and well known treatise among students of Singapore history, but Li Qinghui's Dongyou jilue 東游紀略 (A Brief Record of the Travel to Eastern Countries) is a historical document "re-discovered" by the author in recent years. It was published only once in the form of serialized essays in a local Chinese newspaper in Singapore, the Lat pao 叻報, from February 12 to March 5, 1889. This paper examines the family and cultural backgrounds of the two Lis and the setting upon which the journals were written, comparing their perceptions and impressions of the "Other" as reflected in their writings. From there we could learn about the living conditions and politico-cultural environment of the two cities in the 1880s. But more importantly, this paper attempts to show that the Lis' gazing at each other not only revealed what they saw in the new environment, but also initiated a process of self reflection and self evaluation in the two men about their own community and their home city. These reflections in turn deepened their commitment of reform in improving the conditions of their own city.