Recommendation algorithms play an important role in the current media landscape by fostering interactions between users of digital media platforms and media content. The growing concern with recommendation algorithms raises important questions for media educators who emphasize critical analysis of media content and creative production and are required to develop media education initiatives focused on a critical understanding of digital platforms and their underlying technical infrastructures. What are teenagers’ current perception and experiences of recommendation algorithms? What should be the key issues these initiatives should address, and how should they be addressed? The In the Shoes of an Algorithm project approached these questions through design-based research (DBR). This project led to the creation of a series of pen-and-paper games designed to (1) help teenagers share their daily experiences of recommendation algorithms to identify core issues that should be addressed by media educators and (2) to foster a better understanding of key issues related to recommendation algorithms used by digital media platforms. The project was initiated in Belgium and expanded as an international program, in collaboration with South-Korean researchers and practitioners.