This study investigated the daily lives of obese children and their families to better understand factors influencing weight-related behaviors. A multiple case study design was implemented with 6 obese children and their families. Participant observations occurred in different settings from when the children woke until they went to bed, yielding approximately 95 hours of data per family. Lack of parenting skills and role modeling, environments encouraging poor weight-related behaviors, low self-awareness and enjoyment of sedentary activities were common themes. Child obesity involves a complex set of factors interacting to place a child at risk of developing weight problems.