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. 

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.

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 been almost two years since Effie’s beloved parents got divorced, destroying the image of the happy, loving childhood she thought she had. Since then, she’s become estranged from her father and embarked on a feud with his hot (and much younger) girlfriend, Krista. And now, more earth-shattering news: They’ve sold Greenoaks, the rambling Victorian country house Effie has always called home.

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. Fifteen years later, Josie and Meredith are in their late 30s, following very different paths.  

Rachel White is the consummate good girl. A hard-working attorney at a large Manhattan law firm and a diligent maid of honor to her charmed best friend Darcy, Rachel has always played by all the rules. But that changes the night of her thirtieth birthday when Rachel finally confesses her feelings to Darcy's fiancé, and is both horrified and thrilled to discover that he feels the same way. As the wedding date draws near, events spiral out of control, and Rachel knows she must make a choice between her heart and conscience.

Claudia and Ben are the perfect couple. Ever since their first date, when they both admitted they had no desire for children, their courtship and marriage seemed destined. Their relationship is about freedom, possibility, and exploration. About being together because they want to be together. Not because children are caging them with 18 years of obligation. But then Ben changes his mind: He does want children, after all.

Darcy Rhone thought she had it all figured out: the more beautiful the girl, the more charmed her life. Never mind substance. Never mind playing by the rules. Never mind karma. But Darcy's neat, perfect world turns upside down when her best friend, Rachel, the plain-Jane “good girl,” steals her fiancé, while Darcy finds herself completely alone for the first time in her life . . . with a baby on the way. Darcy tries to recover, fleeing to her childhood friend living in London and resorting to her tried-and-true methods for getting what she wants.

Lottie is tired of long-term boyfriends who don’t want to commit to marriage. When her old boyfriend Ben reappears and reminds her of their pact to get married if they were both still single at 30, she jumps at the chance. There will be no dates and no engagement - just a straight wedding march to the altar! Next comes the honeymoon on the Greek island where they first met. But not everyone is thrilled with Lottie and Ben’s rushed marriage, and family and friends are determined to intervene. Will Lottie and Ben have a wedding night to remember…or one to forget?