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.

First comes love. Then comes marriage. Then comes...a baby carriage? Isn’t that what all women want? Not so for Claudia Parr. And just as she gives up on finding a man who feels the same way, she meets warm, wonderful Ben. Things seem too good to be true when they fall in love and agree to buck tradition with a satisfying, child-free marriage. Then the unexpected occurs: one of them has a change of heart.

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.

Tessa Russo is the mother of two young children and the wife of a renowned pediatric surgeon. Despite her own mother's warnings, Tessa has recently given up her career to focus on her family and the pursuit of domestic happiness. From the outside, she seems destined to live a charmed life. Valerie Anderson is an attorney and single mother to six-year-old Charlie - a boy who has never known his father.

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.