At age thirty-three, Penelope “Pepper” Bradford has no career, no passion and no children. Her intrusive parents still treat her like a child. Moving into the Chelmsford Arms with her fiancé Rick, an up-and-coming financier, and joining the co-op board give her some control over her life—until her parents take a gut dislike to Rick and urge Pepper to call off the wedding. When, the week before the wedding, she glimpses a trail of desperate text messages from Rick’s obsessed female client, Pepper realizes that her parents might be right.

She looks to her older neighbors in the building to help decide whether to stay with Rick, not realizing that their marriages are in crisis, too. Birdie and George’s bond frays after George is forced into retirement at sixty-two. And Francis alienates Carol, his wife of fifty years, and everyone else he knows, after being diagnosed with an inoperable heart condition. To her surprise, Pepper’s best model for love may be a clandestine romance between Caleb and Sergei, a porter and a doorman.