This study used grounded theory methodology (B. G. Glaser & A. L. Strauss, 1967; A. Strauss & J. Corbin, 1990) to explore the help-seeking behaviors of a select group of White male adolescents to understand and identify the mental health stressors in their lives and the factors involved with their decisions to seek or not to seek help for those stressors. Semistructured interviews were conducted with 22 males, 4 female adolescent counterparts, 4 male parents, and 5 high school staff members. The substantive grounded theory that emerged was that the communal pressures of wealth, success, and high expectations creates a tremendous amount of stress for males to be successful and "fit in" and contributes to a gender-linked stigma about males' help-seeking behaviors. Specific motivators and barriers to help seeking are identified and discussed, as are common methods and resources used by males to deal with personal problems. Finally, suggestions for making professional helping services more acceptable to this population are presented, and specific research directions are posited.