Every summer, four college friends hold a mini reunion. They laugh, reminisce, and commiserate about their soul-sucking jobs. Maybe they should have listened to everyone who warned them to study something "practical". Then an unexpected windfall arrives - $1 million, to be exact - with the stipulation that they use it to jump-start their new careers. Almost overnight, a professor, a bartender, a copywriter, and an administrative assistant reinvent themselves.

Ellie married her handsome, wealthy Prince Charming when she was young, naive, and willing to sign a one-sided pre-nup in the name of true love. But seven years and one toddler later, her happily ever after has come screeching to a halt. If she can't save her marriage, she's determined to save her divorce, and she's not about to let a lot of legalese stand in her way.

Home to the Better Off Bed-and-Breakfast, the Eat Your Heart Out bakery, and the Whinery bar, Black Dog Bay offers a haven for the suddenly single. Flight attendant Summer Benson lives by two rules: Don't stay with the same man for too long, and never stay in one place. She's about to break rule number one by considering accepting her boyfriend's proposal - then disaster strikes, and her world is shattered in an instant.

After enduring a chaotic childhood, Emily McKellips yearns for a drama-free life, complete with a white picket fence. Her dreams are about to come true: She has a stellar career, a gorgeous house, and a fiancé any woman would die for. But as friends and family arrive in picturesque Valentine, Vermont, for her wedding, an uninvited guest shows up. Ryan is Emily's first husband from a disastrous starter marriage. They wed on a whim, only to discover that combustible chemistry couldn't ensure a happily ever after.

Sasha has had it. She cannot bring herself to respond to another inane, “urgent” email or participate in the corporate employee joyfulness program. She hasn’t seen her friends in months. Sex? Seems like a lot of effort. Even cooking dinner takes far too much planning. Sasha has hit a wall. Armed with good intentions to drink kale smoothies, try yoga, and find peace, she heads to the seaside resort she loved as a child. But it’s the off season, the hotel is in a dilapidated shambles, and she has to share the beach with the only other occupant: a grumpy guy named Finn.

After a political scandal, fledgling lobbyist Dempsey Jo Killebrew is left almost broke, unemployed, and homeless. She reluctantly accepts to refurbish Birdsong, the old family place in Guthrie, Georgia. But, oh, is Dempsey in for a surprise. "Bird Droppings" would more aptly describe the moldering Pepto Bismol - pink dump. There's also a murderously grumpy old lady who has claimed squatter's rights and isn't moving out. Ever.

Andrea Sachs, a small-town girl fresh out of college, is hired as the assistant to Miranda Priestly, the successful editor of Runway magazine. Andrea finds herself in an office that shouts Prada! Armani! Versace! at every turn. As things escalate from the merely unacceptable to the downright outrageous, Andrea begins to realize that the job a million girls would die for may just kill her. And even if she survives, she has to decide whether the job is worth the price of her soul.

Twenty-nine-year-old Lindsey Rose has, for as long as she can remember, lived in the shadow of her ravishingly beautiful fraternal twin sister, Alex. Determined to get noticed, Lindsey is finally on the cusp of being named VP creative director of an elite New York advertising agency, after years of 80-plus-hour weeks, migraines, and profound loneliness. But during the course of one devastating night, Lindsey’s carefully constructed life implodes. Humiliated, she flees the glitter of Manhattan and retreats to the time warp of her parents’ Maryland home.

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.

Amanda Beth Luker has spent her whole life desperately looking for someone who can show her the way out of her trailer park Florida town. And then, finally, help arrives - in the form of Tom Davis, a successful lawyer with political aspirations who grew up just a few towns over from Amanda. But it's his wife, Lindsay, who really captures Amanda's imagination. Strong, smart, and determined, she gives Amanda something she's never had: a role model.

Actuary Penny Sinclair has a head for business, and she always makes rational decisions. Knowing that 60 percent of spouses cheat and 50 percent of marriages end in divorce, she wasn't too surprised when her husband had an affair. (That he did so with a woman their daughter's age? Well, that part did sting a bit.) She just made sure she got everything in the divorce, including their lovely old Victorian house. And as soon as her younger daughter has her hipster-fabulous wedding in the backyard, she's trading it in for a condo in downtown Chicago....

Rory McGovern is entering the prime of her life when her husband loses his dream job and announces he feels like "taking a break". Rory was already spread thin and now, without warning, she is single-parenting two kids, juggling their science projects, flu season, and pajama days, while coming to terms with her disintegrating marriage. Without Blake, her only hope is to accept a full-time position working for two full-time 20-somethings.

No political science degree could ever prepare Elizabeth Miller for her new job as a second assistant at The Agency, whose clients include everyone you’ve never met - but you know who they’re sleeping with. A former congressional intern in Washington, Lizzie made a bid for a life change that landed her a job a world away, where ethics and First Amendment debates take a backseat to pleading the Fifth for Ritalin-snorting boss Scott Wagner.

Charlie Goldwyn's life hasn't exactly gone according to plan. A widower at 34, he is left trying to raise a quirky five-year-old, Caleb, whose obsession with natural disasters and penchant for girls' clothing have made him a loner at his preschool. The only thing Charlie does have going for him is his job at a prestigious law firm where - after 10 long years of 12-hour days and working through weekends and a huge win on a settlement - he is finally a rising star on his way to becoming a partner.

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.