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.

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.

Marian Caldwell is a 36-year-old television producer, living her dream in New York City. With a fulfilling career and satisfying relationship, she has convinced everyone, including herself, that her life is just as she wants it to be. But one night, Marian answers a knock on the door ... only to find Kirby Rose, an 18-year-old girl with a key to a past that Marian thought she had sealed off forever. From the moment Kirby appears on her doorstep, Marian’s perfectly constructed world - and her very identity - will be shaken to its core.

Growing up, Josie and Meredith Garland shared a loving, if sometimes contentious, relationship. Josie was impulsive, spirited, and outgoing, Meredith hardworking, thoughtful, and reserved. When tragedy strikes, their delicate bond splinters.

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.