This qualitative data analysis examined adolescents' thoughts and feelings about difficulties that can emerge during sexual experiences. The sample consisted of 53 sexually experienced, ethnically diverse, predominantly female, nonpregnant adolescents participating in a web-based sexual health intervention. As part of a message board discussion, adolescents described anxiety-enhancing attitudes and beliefs (e.g., men should be skilled sexually, women should express satisfaction even if they do not feel it). Several adolescents advocated for condom use despite potential difficulties when attempting to use them. Health professionals should equip adolescents with skills to communicate with partners about sexual difficulties and cope with related anxiety.