Telltales - Gamifying Personal Fitness Journey" explores the evolution and challenges of the online fitness industry. The project traces the journey of fitness culture from VHS workout tapes with icons like Jane Fonda to the rise of modern digital platforms such as Beachbody and MyFitnessPal. By combining primary and secondary research, the project identifies key pain points for both trainers and clients in online fitness. Trainers struggle with maintaining engagement, communication, and offering personalized feedback, while clients face challenges with motivation, consistency, and trust in digital fitness programs. The project proposes gamification and personalized narratives as innovative solutions to these problems, enhancing user engagement and improving fitness outcomes. By incorporating game-like elements and personalized stories, the fitness journey becomes more interactive and motivating. The culmination of this research is the design of an app that uses these principles to boost client motivation and retention in remote coaching scenarios. "Telltales" aims to transform the online fitness experience, making it more enjoyable, engaging, and effective for users and trainers alike. The project highlights the potential of gamification in overcoming the challenges of online fitness, creating a new paradigm in the fitness industry.