The present study examined the link between the emotional context of sexual situations and sexual risk, specifically by examining the relationship of teens’ recall of their affective states prior to sex with their sexual risk behaviors and attitudes. Adolescents (ages 13-19) attending therapeutic schools due to emotional and behavioral difficulties (n = 247) completed audio computer-assisted self-interviews regarding sexual behavior, including ratings of their emotions prior to last sexual activity. Positive emotions were most commonly endorsed (43-57 % of participants), however, significant proportions (8-23 %) also endorsed negative emotions prior to last sex. Both positive and negative emotions were significantly related to risk attitudes and behavior in regression analyses. The affective contexts of sexual experiences may be important predictors of risk in adolescence.