The present study examined occasion-level associations between cognitions (willingness to drink, descriptive norms, and injunctive norms) and situational factors (familiarity with people and locations) with playing drinking games (DGs) among adolescents and young adults. Further, this study tested the associations between playing DGs, the number of drinks consumed, and the negative consequences experienced at the occasion level. Participants were 15–25-year-olds (N = 688; 43 % male, 47 % White, Non-Hispanic, Mean age = 21.18) who were part of a longitudinal ecological momentary assessment (EMA) study on cognitions and alcohol use. The study design consisted of a 3-week EMA burst design (8 surveys per week) that was repeated quarterly over the 12-month study (up to 2x/day) per participant. Multilevel models showed that occasion-level risks (higher willingness, higher descriptive norms, and less familiarity with people) were associated with playing DGs. When examining the within-person associations between DGs and number of drinks, results showed that playing DGs was associated with consuming more drinks. For consequences, DGs were not uniquely predictive of experiencing more consequences and riding in a vehicle with a driver who had been drinking. This study contributes to the literature by examining associations between cognitions and situational factors with DGs and the role DGs play in experiencing negative consequences among a diverse sample of adolescents and young adults.