The purpose of this study is to examine the complexities of recruiting overweight and obese adolescent boys for qualitative research, discuss specific recruitment considerations for this population, and offer guidance to researchers interested in recruiting overweight adolescent boys. Three overweight adolescent boys and six community professionals participated in this study. Data collection methods included fieldwork observations (60 hours) and person-centered interviews (N=9). Emergent themes revealed that establishing trust, understanding the sensitivities of discussing obesity, and considering adolescent boys’ fears of sharing personal information may have enhanced recruitment success. Researchers should consider the importance of building relationships with professionals who can recruit vulnerable adolescents, as well as the time required to establish trust with both overweight adolescent boys and their parents. Keywords: Adolescent Boys; Overweight; Obesity; Recruiting Vulnerable Populations; Community; Qualitative Research