People living with HIV (PLHIV) on anti-retroviral treatment (ART) who drink are less adherent and more likely to engage in unprotected sex but the connections among these events are correlational. Using an adapted Timeline Follow-Back (A-TLFB) procedure, this paper examines the day by day interface of alcohol, medication adherence and sex to provide a fine grained understanding of how multiple behavioral risks coincide in time and space, explores concordance/discordance of measures with survey data and identifies potential recall bias. Data are drawn from a survey of behavior, knowledge and attitudes, and a 30 day TLFB assessment of multiple risk behaviors adapted for the Indian PLHIV context, administered to 940 alcohol-consuming, HIV positive men on ART at the baseline evaluation stage of a multilevel, multi-centric intervention study. On days participants drank they were significantly more likely to be medication non-adherent and to have unprotected sex. In the first day after their alcohol consuming day, the pattern of nonadherence persisted. Binge and regular drinking days were associated with nonadherence but only binge drinking co-occurred with unprotected sex. Asking about specific “drinking days” improved recall for drinking days and number of drinks consumed. Recall declined for both drinking days and nonadherence from the first week to subsequent weeks but varied randomly for sex risk. There was high concordance and low discordance between A-TLFB drinking and nonadherence but these results were reversed for unprotected sex. Moving beyond simple drinking-adherence correlational analysis, the A-TLFB offers improved recall probes and provides researchers and interventionists with the opportunity to identify types of risky days and tailor behavioral modification to reduce alcohol consumption, nonadherence and risky sex on those days.