Motivational factors play a significant role in weight loss. Providing appropriate support based on an individual’s motivational level could be a deciding factor in weight loss success. Considering the high cost of obesity to public health care, a system with the ability to assess motivation could benefit individuals and the public alike. As self-report measures are not always available and would be tedious to use on a regular basis, one way to achieve this understanding could be the interpretation of natural language. This project studies the feasibility of using conversational agents to measure motivation by engaging users in natural conversation during weight loss. This approach could be a good means of tracking motivation, as it is cheap and accessible and can model motivation in a more natural and engaging way than self-report measures.