Conversational agents have made significant progress since ELIZA, expanding their role across various domains, including healthcare, education, and customer service. As these agents become increasingly integrated into daily human interactions, the need for emotional intelligence, particularly empathetic listening, becomes increasingly essential. In this study, we explore how Large Language Models (LLMs) respond when tasked with generating emotionally rich interactions. We analyzed the emotional progression of the dialogues using both sentiment analysis (via VADER) and expert assessments. While the generated conversations often mirrored the intended emotional structure, human evaluation revealed important differences in the perceived empathy and coherence of the responses. These findings suggest that emotion modeling in dialogues requires not only structural alignment in the expressed emotions but also qualitative depth, highlighting the importance of combining automated and human-centered methods in the development of emotionally competent agents.