Measuring empathy as a natural language processing task has often been limited to a subjective measure of how well individuals respond to each other in emotive situations. Cognitive empathy, or an individual’s ability to accurately assess another individual’s thoughts, remains a more novel task. In this paper, we explore natural language processing techniques to measure cognitive empathy using paired sentence data from design interviews. Our findings show that an unsupervised approach based on similarity of vectors from a Large Language Model is surprisingly promising, while adding supervision does not necessarily improve the performance. An analysis of the results highlights potential reasons for this behaviour and gives directions for future work in this space.