This paper presents the analysis of over 4,000 chat questions from 2019-2020. Each chat question was individually categorized into broad level topics, and analyzed using sentiment analysis. During the COVID pandemic, there was an increase in the number of questions about accessing the physical collection, and a large decrease in questions about using the library space. The overall sentiments of the chat questions were much more negative during COVID. Tagging and analyzing chat questions in this way can offer unique insights for all types of libraries to appropriately staff the service and best support patron needs in times of crisis.