Empathy, originally a psychological term, is applied to research fields of communication, rhetoric, and narration. A few papers touch on the relation between empathy and translation. However, few studies integrate empathy and communication with translation to deal with out-going translation and communication of Chinese culture. This paper breaks through the disciplinary barriers among psychology, translation, and communication, puts forward a new concept of empathetic trans-communication, constructs its mechanism of "guidance-contagion-cognition-behavior," and explores its practical approach to the translation of Chinese classics by taking Tsai Chih-chung’s comics as a case study. The mechanism is a two-way cultural communication process in which the translator adopts specific translation strategies to guide and infect the target audience's emotion according to the communication effect to develop their empathy towards Chinese culture and enable them to engage in a second communication. The mechanism has both theoretical and practical significance for the improvement of the translation theory system and the out-going translation practice of Chinese culture.