In this article, the authors present the results of the analysis of the baseline data fromKeepin’it R.E.A.L.!, an HIV prevention project developed for mothers and their adolescents. Six hundred twelve mostly male (60.6%) and African American (98.2%) adolescents completed baseline assessments. Eleven percent of the adolescent participants reported initiating sexual intercourse. Adolescent participants expressing higher levels of self-efficacy to resist peer pressure, more favorable outcome expectancies, less communication about sex with their mothers, higherle vels of self-concept related to theirbeha vior, lowerle vels of self-concept related to popularity, and less stress reported fewer types of intimate sexual behaviors. Adolescent participants who reported higher selfefficacy to resist peer pressure to have sex and lower levels of stress were less likely to have initiated sexual intercourse. Selected characteristics of mothers did not contribute to understanding factors associated with intimate sexual behaviors or initiation of sexual intercourse among adolescent participants.