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.

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.

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.

Four freshmen arrive at college from completely different worlds: Lainey, a California party girl with a flair for drama; Tyson, a brilliant scholar and aspiring lawyer from Washington, D.C.; Summer, an ambitious, recruited athlete from the Midwest; and Hannah, a mild-mannered southerner who is content to quietly round out the circle of big personalities. Soon after arriving on campus, they strike up a conversation in their shared dorm, and the seeds of friendship are planted.

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.