Using a developmental-contextual framework, the present study investigated risk factors for same- and cross-gender sexual harassment victimization in 986 middle school students. Participants completed questionnaires in the fall and spring of the same school year so risk factors could be explored longitudinally. Results revealed that gender differences existed for same- and cross-gender forms of harassment. While girls reported more instances of receiving same- and cross-gender unwanted sexual attention, boys were more likely to report being victims of same-gender gender harassment. Important differences in risk factors also existed. Being bullied in the fall and feeling disconnected from school were risk factors for same-gender victimization but not for cross-gender victimization. Romantic relationship status, which was a significant risk factor for both same- and cross-gender victimization, was qualified by significant gender interactions. Results are explained through a developmental-contextual lens and implications for intervention are discussed.