Young men who have sex with men (YMSM) between the ages of 13 and 24 account for a disproportionate number of new HIV infections in the U.S. Recognizing the unique developmental circumstances that YMSM face and building on the dual-process model, it is important to consider the role of cognitive and emotional factors as well as self-efficacy to negotiate safer sex when understanding experiences of sexual risk-taking among YMSM. This article used structural equation modeling to examine how the decisional balance to use condoms (a cognitive factor) and limerence (an emotional factor) are both directly and indirectly associated with sexual risk-taking behaviors (the number of insertive and receptive condomless anal intercourse partners), with indirect effects occurring via limited self-efficacy to negotiate safer sex. Data were from a cross-sectional online survey of YMSM (aged 18-24) in the U.S. who did not report being in a romantic relationship. Analysis included a sample of 1084 single YMSM who had never tested positive for HIV and who had engaged in anal intercourse in the previous 2 months. Results indicated that the decisional balance to use condoms was both directly and indirectly associated with reduced sexual risk-taking behaviors. Limerence was not directly associated with sexual risk-taking behaviors; however, it was indirectly associated with sexual risk-taking behavior through limited self-efficacy to negotiate safer sex. These findings highlight the importance of considering both cognitive and emotional factors, as well as self-efficacy to use condoms, in the development and implementation of HIV prevention interventions for YMSM.