Rachel has always been a good girl--until her 30th birthday, when her best friend Darcy throws her a party. That night, after too many drinks, Rachel ends up in bed with Darcy's fiancé Dex. Rachel is horrified to discover that she has genuine feelings for Dex. She prays for fate to intervene, but when she makes a choice she discovers that the lines between right and wrong are blurry, endings aren't always neat, and you have to risk all to win true happiness.

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.

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.

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.