This study examined cross-sectional and 5-year longitudinal associations between the frequency of family meals and overweight status (>85th percentile for age and gender) in a large, diverse population of adolescents (n = 2,516). The population included two cohorts (midadolescence to young adulthood, n = 1,710, and early adolescence to midadolescence, n = 806). Logistic regression models tested cross-sectional and longitudinal (1999–2004) associations between family meal frequency and overweight status. Two sets of models are presented: (i) models adjusted only for baseline demographic characteristics and (ii) models also adjusted for physical activity, sedentary behaviors, and energy intake. Longitudinal models adjusted for baseline overweight status. Although significant inverse associations between family meal frequency and overweight status were observed for early adolescent females in all cross-sectional models (P < 0.001), longitudinal associations were not significant. Neither cross-sectional nor longitudinal associations were significant for males of either cohort and older females in any models. Young adolescent females who do not eat meals with their families may be at risk for overweight; however, the increased risk may not persist over a 5-year period. Eating family meals during high school may not protect against overweight during young adulthood. Although previous longitudinal research has suggested significant dietary and psychosocial benefits related to family meal frequency, the weight-related benefits of family meals may be more complex and deserving of further study, including an examination of the quality and quantity of food consumed at family meals.