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.

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.

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.

The Kingsley family is American royalty, beloved for their military heroics, political service, and unmatched elegance. In 1967, after Joseph S. Kingsley, Jr. is killed in a tragic accident, his charismatic son inherits the weight of that legacy. But Joe III is a free spirit—and a little bit reckless. Despite his best intentions, he has trouble meeting the expectations of a nation, as well as those of his exacting mother, Dottie.

Four freshmen arrive at college from completely different worlds: Lainey, a California party girl with a flair for drama; Tyson, a brilliant scholar and aspiring lawyer from Washington, D.C.; Summer, an ambitious, recruited athlete from the Midwest; and Hannah, a mild-mannered southerner who is content to quietly round out the circle of big personalities. Soon after arriving on campus, they strike up a conversation in their shared dorm, and the seeds of friendship are planted.