Research demonstrates a consistent association between substance use and sexual risk, particularly among men who have sex with men (MSM). The present study builds upon two existing theories (Cognitive Escape Theory and Expectancy Theory) to examine the synergistic role of sexual conflict (surrounding unsafe sex) and expectancies in sexual behavior among 135 MSM. Two conflicts were examined: (1) The conflict between motivation to practice safer sex and temptation for unprotected sex; and (2) The conflict between motivation to practice safer sex and perceived benefits of unprotected sex. Factorial ANOVAs (2 × 2; high versus low expectancies and conflict versus no conflict) revealed a significant interaction between conflict and expectancies-individuals who reported high levels of conflict were more sensitive to the effect of expectancies than were those experiencing low levels of sexual conflict. Results demonstrate the synergistic effects of conflict and expectancies and highlight the importance of integrating existing theories to more fully consider the intrapsychic operation and experience of sexual conflicts.