Decision-making processes in everyday life are complex. Research on decision-making has focused on self-report or experimental paradigms to understand this process. Recent work has highlighted the potential for complex iterative decision-making frameworks. We developed a simulated decision-making paradigm to assess the relationship between in-game and real-world behaviors and symptoms of depression through exploratory and then pre-registered, confirmatory analyses. Our pre-registered and post-hoc confirmatory analyses highlighted the link between in-game technology use and real-world technology use. We also explored decision-making through transition probabilities to evaluate how specific decisions might unfold over time. The findings emphasized the stability of discrete decision-making in two independent samples. Taken together, these findings suggest that some behavioral patterns appear to be quite stable. Our novel “game” has the potential to provide important insights into decision-making processes and may provide a unique method for identifying and intervening on specific targeted behaviors.