Ashley Randall's struggle with food and weight began when she was a child. Her mother often tried to curb her daughter's eating habits, but Ashley found those attempts more harmful than helpful. While her mother admonished Ashley's eating with insults and teasing, her father would often tell his wife to let Ashley be. The household's dynamic resulted in Ashley favoring her father and avoiding her mother.

During the first few years of her weight loss journey, Ashley showed significant progress. After undergoing gastric bypass surgery and two excess skin removal surgeries, she slimmed down to 265 pounds by the end of her fifth year working with Dr. Now. Then, during her sixth year in the program, tragedy struck. Ashley's father, who was one of her most important motivations for losing weight, was diagnosed with cancer. Ashley put her education on hold and moved back in with her family to care for her ailing father. Seven months after being diagnosed, Ashley's father died.