Once upon a time, Catherine Andrews (Joley Collins) was an aspiring novelist, creating life-changing stories of hope and optimism. That has changed. After losing her daughter in a car crash many years ago, Catherine gave up on her dreams and fell into a life of maxed-out credit cards, divorce, and complacency, working as an assistant for a publisher of exploitative disaster novels. However, her life is one again turned upside down, after her deceased daughter secretly re-appears as a variety of colorful characters: a comical fumigator, a wise hobo, and a caring waitress (played by Kelly McGillis).
Each of them silently proceed to take away every aspect of her false and unhappy life. This leaves her with literally nothing, except to re-discover the kind nature of her true self. Once again, Catherine begins to dream and tell stories... What Could Have Been recalls the golden age of cinema, and is modeled after such inspiring films as It's a Wonderful Life and Charles Dickens' A Christmas Carol.