Empathy is essential in understanding the user’s experience. However, the relationship between the different empathy constructs, such as empathic mental processes and empathic understanding (EU), remains unclear. Therefore, in this study, we explore EU from both the designer’s and the user’s perspectives and how it relates to empathic mental processes. Specifically, we investigate the relationship between the user’s perceived empathic understanding (PEU) and the designer’s actual EU. We also examine the role of mental processes, specifically verbal mimicry, measured as Language Style Matching (LSM), in developing EU during interviews. The results show a relationship between PEU and EU, but no correlation between verbal mimicry and either perceived or actual EU. However, our results show that verbal mimicry indicates the user’s expressiveness during the conversation, which may facilitate the relationship between PEU and EU. We find that when both mimicry is high and the user perceives the designer as empathic, the designer’s EU is almost always high, and vice versa; however, this is less predictable in interviews with low mimicry. We conclude that treating empathic mental processes as a prerequisite for developing and attaining EU might be more useful than investigating a relationship.