Nina Browning is living the good life after marrying into Nashville's elite. More recently, her husband made a fortune selling his tech business, and their adored son has been accepted to Princeton. Yet sometimes the middle-class small-town girl in Nina wonders if she's strayed from the person she once was. Tom Volpe is a single dad working multiple jobs while struggling to raise his headstrong daughter, Lyla. His road has been lonely, long, and hard, but he finally starts to relax after Lyla earns a scholarship to Windsor Academy, Nashville's most prestigious private school.

The Kingsley family is American royalty, beloved for their military heroics, political service, and unmatched elegance. In 1967, after Joseph S. Kingsley, Jr. is killed in a tragic accident, his charismatic son inherits the weight of that legacy. But Joe III is a free spirit—and a little bit reckless. Despite his best intentions, he has trouble meeting the expectations of a nation, as well as those of his exacting mother, Dottie.

It’s 2 AM on a Saturday night in the spring of 2001, and 28-year-old Cecily Gardner sits alone in a dive bar in New York’s East Village, questioning her life. Feeling lonesome and homesick for the Midwest, she wonders if she’ll ever make it as a reporter in the big city - and whether she made a terrible mistake in breaking up with her longtime boyfriend, Matthew.

Thirty-three-year-old Shea Rigsby has spent her entire life in Walker, Texas - a small college town that lives and dies by football, a passion she unabashedly shares. Raised alongside her best friend, Lucy, the daughter of Walker’s legendary head coach, Clive Carr, Shea was too devoted to her hometown team to leave. Instead she stayed in Walker for college, even taking a job in the university athletic department after graduation, where she has remained for more than a decade.

Ellen and Andy's first year of marriage doesn't just seem perfect, it is perfect. There is no question how deep their devotion is, and how naturally they bring out the best in each other. But one fateful afternoon, Ellen runs into Leo for the first time in eight years. Leo, the one who brought out the worst in her. Leo, the one who left her heartbroken with no explanation. Leo, the one she could never quite forget. When his reappearance ignites long-dormant emotions, Ellen begins to question whether the life she's living is the one she's meant to live.