Sexual health education (SHE) provides students with knowledge and skills to establish healthy relationships, understand sexual development, and prevent risk behaviors; therefore, it is critical to understand how to optimize the delivery and receipt of this education. Using a grounded theory approach, interviews with middle school health education teachers (n = 13) and focus groups with students (n = 41) were conducted to examine factors that influence perceived comfort delivering and receiving SHE in a public-school district. Findings identified key barriers including disruptive behavior, insufficient time, and lack of dedicated classrooms. Some key facilitators to comfort included professional development and establishing ground rules.