The present paper aims to explore the performance of Sympathize as a speech act by advanced learners of Chinese as a foreign language (CFL). We collected data from both 16 advanced CFL learners and 16 native speakers of Chinese through a DCT, and we then asked 10 native speakers of Chinese to rate the appropriacy of the DCTs provided by the two groups. The results of our analysis show that the language use of native speakers and advanced learners only differed significantly when they employed three strategies “Minimize the negativity of the events,” “Analyze the negative events objectively,” and “Look at problems from a positive perspective,” while their behavior only marginally differed when it came to the two strategies of “Release the listeners’ negative emotions” and “Encourage.” However, learners received overall lower scores than native speakers regarding the appropriateness of their sympathizing expressions.