Mental well-being is a critical aspect of overall health, particularly for college-going students, who face increasing levels of stress, anxiety, and depression. The Oxford Happiness Questionnaire (OHQ) has been a standard tool to assess mental health in multiple contexts, including educational settings. However, the self-reported nature of the OHQ leads to challenges like lack of engagement and the occurrence of biases. Conversely, gamification is a concept that has proven to be effective in increasing engagement. Therefore, this study proposes a novel approach by incorporating gamification strategies with OHQ to enhance user engagement and assess the mental well-being of college-going students. A gamified application called “The Mirror” has been developed using a ‘research-through-design’ approach. The study utilized a mixed-method methodology to compare the traditional OHQ with the gamified application in terms of user engagement and experience. Results from a pilot study indicate that the gamified OHQ increased engagement and provided a more enjoyable and personalized assessment experience compared to the traditional format. The findings suggest that integrating gamification into the OHQ can improve its efficacy as a self-guided questionnaire, making it more effective in assessing mental well-being. Future research with larger sample sizes and real-world testing is recommended to further refine the gamified application and validate its effectiveness.