Background: Sources of sexual health information exert strong influence on adolescents' sexual behavior. Purpose: The current study was undertaken to understand how family serve as sexual information sources, the messages adolescents recall from family, and how family learning experiences affect sexual behavior among at-risk adolescents. Methods: Individual interviews were conducted with 69 teens, ages 15-18 years, from an alternative high school and a juvenile correctional facility to capture adolescents' early sexual health learning experiences involving family and evaluate their association with teens' recent sexual behavior. Sexual learning narratives were compared among gender and sexual experience groups. Results: Many participants identified family as sexual health information sources. Primary messages recalled: risks of sex, protection, and relationship advice. Many adolescents portrayed learning experiences as negative, cautionary, lacking detail and not always balanced with positive messages. Participants who reported four or more sexual risks were the only group to identify pornography as a sexual health information source. Participants who reported fewer than four sexual risks were most likely to identify family sexual health information sources. Discussion: Participants identified family members as sources of sexual health information, with variations by gender. Negative/cautionary messages require teens to seek additional sexual information elsewhere (primarily friends/media). Males, in particular, appear to often lack familial guidance/education. Translation to Health Education Practice: Sexual health messages should be tailored to adolescents' needs for practical and sex-positive guidance regarding mechanics of sex and formation of healthy relationships, and balanced with cautions regarding negative consequences. (Contains 2 tables.)