In 2012, THAT Theatre Troupe performed two site-specific works, Paintings and Private Letter, in the former residence of the painter Kuo Po-Chuan. The first work was the first time for this place to combine the theatre with outdoor performance space, and performance space of the second work was actually inside Kuo's previous residence. Both of these works combined a specific historical space with a site-specific performance, and they represented real-life stories about the characters who actually lived in the place before. Moreover, they also focused attention on the Japanese official residences of the Japanese colonial period, which are now in Alley 321, Park Road in Tainan City, leading to serious discussions on preserving historical and cultural heritage. The performances of these two works promoted the cultural value of these monuments to the government, and in the following year the area was formally designated as ＂Art Alley 321 settlements＂, becoming a place for artists' creation and life. In this paper, the author separately discusses the two main characters: Zhu Wan-Hua and Kuo Wei-Mei who play females from two different generations within the post-colonial diaspora society, and investigates how to they narrate their sensitive and delicate life stories in the theatre. Inevitably they produce a tight-knit relationship alongside the important male figure, Kuo Po-Chuan. The two works chosen for performance in the residence of Kuo Po-Chuan echoed the dramatic core of the artist, and won the attention of the audience. Finally, they lead the spectators to consider, take interest and develop an understanding of site-specific performance.