This article describes the development and evaluation of The Game of Late Life—a novel education activity for the psychology of ageing. The game was designed to provide transformational learning where students imagine themselves as older adults and move through late life via a game board, encountering various life events along the way. One of the key features of the game is that several of the life event outcomes (moves on the board) are dependent on the how the player interprets and responds to that event. The activity was evaluated across two semesters. In the first study, playing the game significantly improved students' attitudes towards ageing, but did not significantly reduce their anxiety about ageing. Open-ended responses indicated the discussion students engaged in during the game was an important factor for transformational learning. The second study replicated and extended the first by adding significantly more instruction to the tutors about fostering discussion and including specific questions about group discussion in the evaluation. Again, playing the game produced significantly more positive attitudes towards ageing, and in this second iteration it also significantly reduced anxiety about ageing. The student ratings of their tutor's ability to foster discussion were significantly related to the changes in these variables. Students also had very positive feedback about the game as an interesting and engaging activity. While this version of the game is designed around the psychology of ageing, the premise would be easily translated to any area of gerontological education across many disciplines.