Wu Zao and Liu Qingyun both are renowned writer in the Quing Dynasty. Wu Zao expresses her feelings and goals via a self-portrait disguised as a male in her work Qiao ying, while Liu Quingyun faces herself and pursues emotion reposing in In Mirror Circle. In these two dramatic works, the interaction between the author, the lead and the self-portrait as well as the thoughts and feelings is definitely worth exploring and analyzing. Though Wu Zao and Qingyun had differing life experiences and different situations, they both had unsatisfying fortune in reality. As a result, they relieve and comfort themselves by painting portraits. This paper based on the two works looks into their life experiences and discusses the impact of social climate then on their creation. With the paper coming along with their poetry works, I’m willing to find out the meaning behind them by utilizing their self-portraits and their dramatic works.