Research has consistently shown that gay/lesbian/bisexual (GLB) or sexual minority youth are at an increased risk for adverse outcomes resulting from the stress caused by continual exposure to negative events (e.g., victimization, discrimination). The present study used a nationally representative sample of adolescents to test mechanisms that may be responsible for the differences in offending behaviors among sexual minority and heterosexual adolescents. Specifically, this study tested whether bisexual adolescents received less maternal support than did heterosexual adolescents because of their sexual orientation, thus increasing the likelihood that they run away from home. This study then examined whether the greater likelihood that bisexual adolescents running away would lead to them committing a significantly higher variety of income-based offenses, but not a significantly higher variety of aggression-based offenses. This study tested the hypothesized mediation model using two separate indicators of sexual orientation measured at two different time points, modeled outcomes in two ways, as well as estimated the models separately for boys and girls. Structural equation modeling was used to test the hypothesized direct and indirect relations. Results showed support for maternal support and running away mediating the relations between sexual orientation and offending behaviors for the model predicting the likelihood of committing either an aggressive or an income offense, but only for girls who identified as bisexual in early adulthood. Results did not support these relations for the other models, suggesting that bisexual females have unique needs when it comes to prevention and intervention. Results also highlight the need for a greater understanding of sexual orientation measurement methodology.