With the COVID-19 pandemic testing humanity worldwide in unforeseen ways, wellbeing assessment has stepped to the foreground of individual health status. Conversational User Interfaces (CUIs) prove promising as an assessment tool, but lacking the means to retain users engaged during the process. This research aims to explore a solution introducing a graphical modality to a CUI, that improves user experience during wellbeing assessment. A psychological projective testing technique was researched, the H-T-P test, which exposes one's personality, mood and feelings through drawing. A system was designed that utilizes a simplified version of the test and image classification to provide a new means of wellbeing assessment. The system's performance and usability show that such an approach is indeed feasible. This paper describes the design process of the system, the resulting prototype and possible improvements for future implementations.