Adolescents tend to consume alcohol and find romantic and sexual partners in mixed-group settings that are unmonitored by adults. Relatively little is known about the influence that dating anxiety may have with these social interactions. A sample of 163 high school students (aged 14-17 years) completed online surveys assessing dating, sex, and alcohol-related measures of behaviors and cognitions. Anxiety in mixed-sex peer group interactions was linked to later ages of first dating relationships and anxiety in dating interactions with fewer sexual experiences. Dating anxiety was not associated with drinking behaviors, drinking motivations, or expectations for alcohol to facilitate sex. Age, but not gender, was related to all adolescent behaviors and drinking motivations, but not social-sexual expectations for alcohol consumption. Implications relate to the provision of education regarding responsible participation in social experiences in ways that promote positive development.