What might have been? This tantalizing question propels a woman on a cross-country adventure to reunite with the men she had loved and let go.

Madison Allen is a renowned, career-driven photographer. Sifting through old photos in her fashionable New York fire-house apartment, she reflects on what could have been. She'd had three men in her life who were very important to her in different ways, but it was the fourth love, her job, which always won in the end.

Consumed by old memories and with a forced pause in her demanding schedule, Maddie embarks on a road trip. She hopes to answer questions about the men she'd loved and might have married in the years after she was left alone with three young children. As Maddie sets off to reconnect with her past in Boston, Chicago and Wyoming, she hopes to learn that the decisions she made long ago were the right ones.