Objectives: The purpose of this research was to examine the social, educational, and psychological correlates of weight status in an adolescent population. It was hypothesized that obese adolescents would differ on psychological, social, and educational variables compared with their non-overweight peers. Research Methods and Procedures: In this cross-sectional study, a population-based sample of 4742 male and 5201 female public school students in the 7th, 9th, and 11th grades responded anonymously to a classroom administered questionnaire. Body mass index was calculated from self-reported height and weight and categorized into four classes of weight status: underweight (<15th percentile), average weight (15th to 85th percentile), overweight (>85th to 95th percentile), and obese (>95th percentile). The questionnaire also included questions about social experiences, psychological well-being, educational experiences, and future goals. Associations of weight status with social, psychological, and educational variables and future goals were explored. Results: After adjustment for grade level, race, and parental socioeconomic status, obese girls, when compared with their average weight counterparts, were 1.63 (95% confidence interval [CI]: 1.16, 2.30) times less likely to hang out with friends in the last week, 1.49 (95% CI: 1.12, 1.98) times more likely to report serious emotional problems in the last year, 1.79 (95% CI: 1.20, 2.65) times more likely to report hopelessness, and 1.73 (95% CI: 1.21, 1.98) times more likely to report a suicide attempt in the last year. Obese girls were also 1.51 (95% CI: 1.09, 2.10) times more likely to report being held back a grade and 2.09 (95% CI: 1.35, 3.24) times more likely to consider themselves poor students compared with average weight girls. Compared with their average weight counterparts, obese boys were 1.91 (95% CI: 1.43, 2.54) times less likely to hang out with friends in the last week, 1.34 (95% CI: 1.06, 1.70) times more likely to feel that their friends do not care about them, 1.38 (95% CI: 1.08, 1.76) times more likely to report having serious problems in the last year, 1.46 (95% CI: 1.05, 0.03) times more likely to consider themselves poor students, and 2.18 (95% CI: 1.45, 3.30) times more likely to expect to quit school. Compared with average weight boys, underweight boys were 1.67 (95% CI: 1.30, 2.13) times more likely to report hanging out with friends in the last week, 1.22 (95% CI: 1.01, 1.49) times more likely to report disliking school, and 1.40 (95% CI: 1.06, 1.86) times more likely to consider themselves poor students. Discussion: Associations of weight status with social relationships, school experiences, psychological well-being, and some future aspirations were observed. Among girls, the pattern of observations indicates that obese girls reported more adverse social, educational, and psychological correlates. Obese as well as underweight boys also reported some adverse social and educational correlates. These findings contribute to an understanding of how adolescent experiences vary by weight status and suggest social and psychological risks associated with not meeting weight and body shape ideals embedded in the larger culture.