Creating conversational systems for niche domains is a challenging task, further exacerbated by a lack of quality datasets. We explore the construction of safer conversational systems for guiding patients in preparing for colonoscopies. This has required a data generation pipeline to generate a minimum viable dataset to bootstrap a semantic parser, augmented by automatic paraphrasing. Our study suggests large language models (e.g., GPT-3.5 and GPT-4) are a viable alternative to crowd sourced paraphrasing, but conversational systems that rely upon language models’ ability to do temporal reasoning struggle to provide accurate responses. A neural-symbolic system that performs temporal reasoning on an intermediate representation of user queries shows promising results compared to an end-to-end dialogue system, improving the number of correct responses while vastly reducing the number of incorrect or misleading ones.