Research shows that gender norms play a notable role in pregnancy prevention, often placing responsibility on females and allowing some males to pursue sexual encounters without considering the consequences of unprotected sex. This paper examines gender differences in attitudes and behaviors related to condom use and birth control among adolescents using survey, focus group, and interview data gathered from the evaluation of Chicago Healthy Adolescents and Teens (CHAT), a comprehensive sexual health education program implemented with adolescents in Chicago Public High Schools. Results indicate that safe sex attitudes and behaviors differ between male and female adolescents, specifically those related to condoms and birth control. Our findings suggest that (i) females have higher knowledge and presumed responsibility for pregnancy prevention, (ii) infrequent condom use among adolescents prioritizes male pleasure over female health needs, and (iii) social norms discourage females, but not males, from accessing and using birth control. We use the Theory of Gender and Power to show how our findings reflect gender dynamics within the United States and explain the potential health implications for adolescent sexual health.