Will leaving positive legacies mean kissing their own happily-ever-after goodbye? If Tim Bergeron got a lifetime achievement award for anything, it'd be managing the iconic rock band, Awestruck, but he'd trade his successful career for the opportunity to prevent his daughter from repeating his mistakes. When a health scare proves time is short, he talks Isabella into a cross-country road trip. His attempts to talk her out of a hasty marriage drive a wedge between them, and it looks like the best he can hope for from the trip is scouting out promising new talent to represent. That is, until he meets Gabby. Widow Gabrielle Voss has responsibilities to her daughter and patients, deep roots in the community, and a dream that scares her. Though she'd never utter it to the people she lives and works among, the truth slips out with Tim, who's not in Many Oaks, Iowa, to stay. As her fiftieth birthday party draws near and an attraction to Tim sparks to life, Gabby realizes she must pursue her dream now-or, more reasonably, never.