It is important to understand situational factors linked to episodes of unprotected sexual intercourse among Latino gay men (LGM), who are disproportionately affected by HIV/AIDS in the U.S. Past research has suggested that participation in difficult sexual situations mediates the relationship between socio-cultural factors and sexual risk behaviors among LGM. This study examined drug use by self and sex partners, interpersonal factors, and other key variables, each examined at the situation-level of analysis, as predictors of episodes of unprotected anal intercourse (UAI) among LGM. Study participants included 270 LGM living in New York City, Miami, and Los Angeles who reported inconsistent condom use during anal intercourse in the last year. Men participated in structured interviews in which they were asked sets of detailed questions about their most recent episode of anal intercourse in which they used condoms, and their most recent anal intercourse episode in which they did not use condoms. Conditional logistic regression was used to compare the relevance of specific situational factors to participants' episodes of UAI and protected anal intercourse. We found that drug use by a sex partner and lacks of discussions about condom use with partners, among other situational factors, were significantly related to episodes of UAI. The findings highlight the importance of considering the impact of sexual situations and interactions with sex partners when studying HIV risk among LGM and when designing interventions.