As cultures are mainly divided into collectivistic and individualistic, members tend to emphasize, through communication, either their position as part of their group or their independence from the group. This emphasis is manifested in using the pragmatic concepts of positive politeness and negative politeness. The present study looks into the reflection of these two cultures in Rockstar’s renowned video game, Red Dead Redemption 2 (2018). It aims at identifying the two cultures as present in the game and showing their significance to its narrative. It fills the gap in the studies of language used within video games as well as its cultural reflections. The study addresses the following question: What are the positive and negative politeness strategies used in Red Dead Redemption 2 (2018), and what are the implications of using these strategies in its narrative? By adopting Brown and Levinson’s (1987) politeness theory, the researcher analyzed the positive and negative politeness used in the scripted dialogue of the in-game cutscenes through the mixed methods approach. The researcher hypothesized that the protagonist shows adherence to a collectivistic culture using positive politeness, and he begins transitioning towards an individualistic culture using negative politeness. The results showed that 75% of the protagonist’s interactions contained positive politeness while only 25% contained negative politeness. This transition explains the protagonist’s loss of trust and loyalty to his group as he begins to witness the futility of maintaining such loyalty. It also supports the overall narrative of the game as well as its cultural foundations.