Currently there is little research on the effects of obesity and self-esteem on family functioning over time, or more specifically, across two generations. The purpose of this dissertation was to examine the connections between supportive parenting, self-esteem, and obesity over time. This dissertation includes two related studies that both utilize a Family Systems Theory to guide the research. Utilizing the Family Transitions Project (FTP), a longitudinal study that examines adolescents and their families over 23 years, this study extends the current literature by examining how maternal supportive parenting during early adolescence influences obesity in late adolescence and ultimately how both of these influence the individual's parent-child relationships with their own children in adulthood. This study also considers the possible effects of self-esteem on the aforementioned relationships. Chapter 2 examined the influence of maternal supportive parenting in early adolescence on the development of self-esteem in middle adolescence and obesity in late adolescence. Chapter 2 also looked at the mediating role of self-esteem on the relationship between supportive parenting and obesity. Chapter 3 continued to build on this foundation and added in the effects of maternal supportive parenting (G1) in early adolescence, G2 self-esteem in middle adolescence, and G2 obesity in late adolescence on G2 supportive parenting expressed towards their own child in adulthood.