My research interests focus on natural language generation (NLG) regarding how to make system outputs more intuitive and comprehensible for the human-user and conversational entrainment and alignment from the perspective of how dialogue systems could or should personalize its responses to the human user. As it relates to NLG, my current work focuses on training a system to auto-generate comments for SQL queries produced by a Text-to-SQL parser. The goal is to make the connection between technical SQL language and the user’s question more transparent. My linguistic training lies primarily at the intersection of computational and socio-linguistics. As such, my curiosities in conversational entrainment and alignment focus on the extent to which conversational agents can or should adjust their language based on human characteristics such as age, race, or gender.