Massively multiplayer online games have become a common research subject in game studies. Several of these studies have focused on how the player interacts with the game and other players through the game, but often the fact is neglected that there are other games besides MMOGs that allow players to interact with each other. Two-player off-line games, for example, also allow for interaction between players, both through the game and in the physical world. This chapter focuses on the improvement of skills while such a game is being played. We use interaction analysis to understand how the player learns to play the game and how to play together with someone else. By observing how players interact with each other and with the game in a setting with only two players, we find different learning situations than one would find in a single-player or MMOG environment. These learning situations show that the formulation of an understanding of a game and the incorporation of the game into the player’s repertoire are obstructed by the repertoire itself, and they show that players may have trouble adapting to a reflective playing style. This case study is part of a larger project on situated play with multiplayer off-line and colocated video games.