Learning about probability can pose difficulties for students at all levels. Performing probability experiments using games can encourage students to develop understandings of probability grounded in real events. In this reflective paper, we explore the thinking of a group of students and teachers as they reasoned about experimental and theoretical probabilities in a game context. We designed a probability lesson based on the game LuLu (McCoy et al., 2007). In this article we share the activity and describe the kinds of explorations that can be facilitated in any secondary school mathematics classroom. We were particularly interested in investigating whether students could construct a bidirectional link between experimental probability and theoretical probability. Overall, the lesson enabled students to gain hands-on experience in data collection and analysis and better comprehend affordances of culturally diverse games.