In recent years, "gender" has emerged as a prism through which North American Jewish educators discuss adolescents and Jewish identity, communal participation, and programming. Jewish organizations have developed a range of youth and professional development initiatives that foster open discussion with adolescents on intimate relationships, sexuality, gender identity, and body image. The initiatives utilize Jewish texts, themes, and values as frames for exploration of gender issues within formal and informal Jewish educational programming. This chapter highlights recently developed curricula, professional development, educator training, and Participatory Action Research, suggesting a shift from "evasion" to "engagement" of gender issues within Jewish education.