The growing gender gap in educational attainment between men and women has raised concerns that the skill development of boys may be more sensitive to family disadvantage than that of girls. Using the National Longitudinal Study of Adolescent to Adult Health (Add Health) data we find, as do previous studies, that boys are more likely to experience increased problems in school relative to girls, including suspensions and reduced educational aspirations, when they are in poor quality schools, less-educated neighborhoods, and father-absent households. Following these cohorts into young adulthood, however, we find no evidence that adolescent disadvantage has stronger negative impacts on long-run economic outcomes such as college graduation, employment, or income for men, relative to women. We do find that father absence is more strongly associated with men's marriage and childbearing and weak support for greater male vulnerability to disadvantage in rates of high school graduation. An investigation of adult outcomes for another recent cohort from the National Longitudinal Survey of Youth, 1997 produces a similar pattern of results. We conclude that focusing on gender differences in behavior in school may not lead to valid inferences about the effects of disadvantage on adult skills.