Differences in philosophy, goals, and ideologies can make research in sexuality education a turbulentterrain. Despite those debates and challenges, there is a significant amount of research on sexuality education in the United States. However, there is significantly less research on sexuality education in middle schools in the United States compared to high schools. Middle schools deserve more attention in social science research due to the developmental needs of students and teacher competency concerns. Sexuality education research in middle schools can help inform professional and curriculum development that supports educators feeling more competent and students feeling engaged, knowledgeable, and more secure in the safety of U.S. schools. As such, my dissertation research sought to do a qualitative investigation into how sexuality education is showing up in three urban middle schools from grades six through eight in the northeast United States. Through a multi-site case study following six teachers, this research investigated sexuality education, explicitly or implicitly, in cross-curricular ways from health and humanities to STEM classes. This research sought to 1) to understand sexuality education in middle schools in a more contextualized way, including what ways educators may encounter sexuality topics and how educators across subjects negotiate instances related to sexuality (e.g., lesson planning, class discussion, and classroom environment) and 2) identify ways to better support pedagogical and classroom approaches. Insights from this study provide implications on teacher perceptions, cross-curricular teacher competency, classroom safety, student engagement, sexualization, adolescent health and well-being.