Stefano emerged as an innovative fitness companion app designed to challenge the conventional approach to health tracking by addressing a critical psychological barrier: users' compulsive tendency to obsess over metrics rather than focus on genuine lifestyle improvement. The mobile application transforms fitness tracking into an interactive experience, where a mischievous digital companion requires users to complete physical challenges before revealing their health statistics. By generating random object detection challenges via smartphone camera, the app strategically prompts users to move and engage with their environment, with challenge difficulty increasing as users request more data. This deliberate friction mechanism serves to combat metric-driven anxiety while indirectly encouraging positive behavioural changes. The app restricts data access during busy periods, further reinforcing the goal of promoting actual physical activity over passive tracking. Designed for individuals struggling with compulsive stat checking, performance-related anxiety, and motivational challenges, Stefano emerged from research revealing how constant metric availability paradoxically reduces user motivation. Traditional fitness apps inadvertently create cycles of performance anxiety by prioritising numbers over movement. The development process highlighted the importance of psychological design in digital health interventions, demonstrating that introducing deliberate friction and personality can significantly enhance user engagement beyond traditional tracking methodologies. Ultimately, Stefano represents more than an app—it's a paradigm shift in how technology can positively influence personal health behaviour by making fitness tracking an active, engaging, and motivational experience.