In this paper, we explore an interaction between a competitive “Counter Strike: Global Offensive” player and her younger brother, whom she is tutoring in his first match in competitive mode. At least two phenomena, intertwined with each other, are prominent in this data excerpt. One is the boy’s consistent orientation to his sister’s instructions, accountable and observable through the work of following them. The other one deals with the intricacies and overlaps of Lebenswelt (life-world) and Spielwelt (game-world) time and how these apparently different temporalities constitute a temporal whole. Analysis suggests that communication in this instructional setting is grounded in gestalt-contextures that embrace multiple embodied forms of interaction such as talk, gesture, gaze, as well as in-game elements (such as rules to follow and goals to achieve), and how important is the re-specification of those elements as a set, not as a mere sum of individual pieces. Moreover, it is discussed how, while in a gameplay context, players use their common-sense reasoning and practices to elaborate strategies and develop skills necessary to successfully reach their goals.