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Conversational agents have become ubiquitous in assisting with daily tasks, and are expected to possess human-like features. One such feature is lexical entrainment (LE), a phenomenon in which speakers in human-human conversations tend to naturally and subconsciously align their lexical choices with those of their interlocutors, leading to more successful and engaging conversations. As an example, if a digital assistant replies “Your appointment for Jinling Noodle Pub is at 7 pm” to the question “When is my reservation for Jinling Noodle Bar today?”, it may feel as though the assistant is trying to correct the speaker, whereas a response of “Your reservation for Jinling Noodle Baris at 7 pm” would likely be perceived as more positive. This highlights the importance of LE in establishing a shared terminology for maximum clarity and reducing ambiguity in conversations. However, we demonstrate in this work that current response generation models do not adequately address this crucial human-like phenomenon. To address this, we propose a new dataset, named MultiWOZ-ENTR, and a measure for LE for conversational systems. Additionally, we suggest a way to explicitly integrate LE into conversational systems with two new tasks, a LE extraction task and a LE generation task. We also present two baseline approaches for the LE extraction task, which aim to detect LE expressions from dialogue contexts