Recruiting participants for research can be a daunting task, even more so when the participants are adolescents. Recruiting young people through schools poses a number of ethical and practical challenges and is subject to stringent overview and regulation. This case study will give readers an example of the challenges and successes in recruiting adolescent boys in high school and securing parental/guardian consent for a doctoral research project. The research uses a mixed-methods evaluative approach to compare boys who did, and boys who did not, participate in a local sexual health promotion/healthy relationship program, focusing particularly on differences in scoring and understandings of masculinity ideologies. The planned recruitment strategies as well as the multiple modifications made throughout the recruitment process will be described. The case study will conclude with several lessons learned in the process of trying to recruit adolescent boys and obtain parent/guardian consent.