The current study examined the relationship between gambling motives and gambling in various social contexts using both retrospective and real-time assessment of gambling social context. Ninety-five young adults (79 males, 16 females; aged 19–24 years) who reported gambling at least 4 times in the past month participated. Scores on the Gambling Motives Questionnaire (GMQ; Stewart & Zack, 2008) were used as a measure of gambling motives (Enhancement, Social, Coping). Data on the social context of gambling (alone, with family, with friends, with strangers) were derived retrospectively from the Gambling Timeline Follow-Back (G-TLFB; Weinstock, Whelan, & Meyers, 2004) as well as in real time using experience sampling (ES) methods (Conner Christensen, Feldman Barrett, Bliss-Moreau, Lebo, & Kaschub, 2003). For both the G-TLFB and ES data, we conducted a series of multivariate regression analyses with the block of gambling motives predicting gambling behaviour in each social context. Across the two assessment methods, coping gambling motives positively predicted gambling alone, whereas social gambling motives negatively predicted gambling alone and positively predicted gambling with friends. These findings suggest that individuals who gamble for particular motives are more likely to do so in specific social contexts.