This study examined area-specific self-esteem scores by sexual behavior relative to adolescents' values concerning participation in sexual intercourse as an unmarried teenager. The sample consisted of 332 students in grades 7–12 from a Southern rural school district. Students were asked if they had ever had sexual intercourse (yes/no) and if they had participated in sexual intercourse in the last month (yes/no). Respondents also indicated on a 4-point scale their response to the statement “It is against my values to have sex as an unmarried teenager.” Data were analyzed using a 2 × 4 (behavior x values) analysis of variance for each of the three area-specific self-esteem scores (peer, school, and home). Results indicated that students who had participated in sexual intercourse had significantly lower scores in school and home self-esteem than those who had not participated. In addition, those who “strongly agreed” with the values statement and indicated they had not had intercourse had the highest school and home self-esteem scores. Those who strongly agreed with the values statement but indicated they had participated in sexual intercourse had the lowest school and home self-esteem scores. This behavior x values interaction was significant for sexual intercourse–ever, and for school self-esteem and sexual intercourse in the last month. No difference was seen in peer self-esteem scores by behavior nor were there behavior x values interactions.