After successfully raising three children on her own, Madison Allen lives as a photographer in New York. An accident in which she suffers a broken ankle prompts her to make a fresh start. Driven by memories and old photos, the forced break from work and a bad fight with her daughter, Madison sets off on a journey into the past. A road trip across the country leads her to three men she once loved and almost married. Before she can look into the future, she faces the open questions of her past: What would have happened if?